Journal Articles | |
| 49. | Volovnenko,; Tarasov,; Zubatyuk,; Shishkin,; Turov,; Volovenko, Yu. Interaction of 2-chloroquinoline- 3-carbaldehydes with 2-hetaryl- acetonitriles (Journal Article) Chemistry of Heterocyclic Compounds, (12), pp. 1489-1502, 2009. @article{Volovnenko20091489, title = {Interaction of 2-chloroquinoline- 3-carbaldehydes with 2-hetaryl- acetonitriles}, author = {Volovnenko, T. A. and Tarasov, A. V. and Zubatyuk, R. I. and Shishkin, O. V. and Turov, A. V. and Volovenko, Yu. M.}, url = {{http://www.scopus.com/inward/record.url?eid=2-s2.0-77950859085&partnerID=40&md5=6144e9694788e8151a765a89cff0f649}, http://www.springerlink.com/index/10.1007/s10593-010-0456-7}, year = {2009}, date = {2009-09-01}, journal = {Chemistry of Heterocyclic Compounds}, number = {12}, pages = {1489-1502}, abstract = {The interaction of 2-chloroquinoline-3-carbaldehydes with 1H-benzimidazol-2-ylacetonitriles and 1-benzyl-1H-imidazol-2-ylacetonitrile has been studied. It was shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The interaction of 2-chloroquinoline-3-carbaldehydes with 1H-benzimidazol-2-ylacetonitriles and 1-benzyl-1H-imidazol-2-ylacetonitrile has been studied. It was shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated. © 2009 Springer Science+Business Media, Inc. |
| 48. | Luzanov,; Zhikol, Electron invariants and excited state structural analysis for electronic transitions within CIS, RPA, and TDDFT models (Journal Article) International Journal of Quantum Chemistry, 110 (4), pp. NA-NA, 2009. @article{Luzanov2010902, title = {Electron invariants and excited state structural analysis for electronic transitions within CIS, RPA, and TDDFT models}, author = {Luzanov, A. V. and Zhikol, O. A.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-74549178106&partnerID=40&md5=97235301209540d1720b925de71eec44, http://doi.wiley.com/10.1002/qua.22041}, year = {2009}, date = {2009-01-01}, journal = {International Journal of Quantum Chemistry}, volume = {110}, number = {4}, pages = {NA-NA}, abstract = {We revisit the interpretative scheme (Luzanov et al., Theor Exp Chem 1974, 10, 354) of singly excited configuration interaction (CIS) model given earlier at semiempirical level. Detailed computations and spectral (natural orbital) treatment of the CIS density matrices of various types are presented. The corresponding hole-particle densities and related excitation localization indices are described. All the quantities are extended to the excited states calculated in the random phase approximation and closely related time-dependent density functional theory (TDDFT). The localization indices and charge transfer numbers which are invoked to describe interfragment interactions provide a basis for our scheme which is referred to as the excited state structural analysis for electronic transitions. The proposed analysis is exemplified by various moderate and large-size conjugated molecules treated within ab initio TDDFT and the Parizer-Parr-Pople approximation. Finally, we propose a possible generalization to the electronic transitions between CIS-like states followed by applications to singlet organic biradicals treated within the $pi$-electron spin-flip CIS.© 2009 Wiley Periodicals, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } We revisit the interpretative scheme (Luzanov et al., Theor Exp Chem 1974, 10, 354) of singly excited configuration interaction (CIS) model given earlier at semiempirical level. Detailed computations and spectral (natural orbital) treatment of the CIS density matrices of various types are presented. The corresponding hole-particle densities and related excitation localization indices are described. All the quantities are extended to the excited states calculated in the random phase approximation and closely related time-dependent density functional theory (TDDFT). The localization indices and charge transfer numbers which are invoked to describe interfragment interactions provide a basis for our scheme which is referred to as the excited state structural analysis for electronic transitions. The proposed analysis is exemplified by various moderate and large-size conjugated molecules treated within ab initio TDDFT and the Parizer-Parr-Pople approximation. Finally, we propose a possible generalization to the electronic transitions between CIS-like states followed by applications to singlet organic biradicals treated within the $pi$-electron spin-flip CIS.© 2009 Wiley Periodicals, Inc. |
| 47. | Kępa,; Majkrzak,; Sipatov,; Fedorov,; Samburskaya,; Giebultowicz, Interlayer coupling in EuS/SrS, EuS/PbSe and EuS/PbTe magnetic semiconductor superlattices. (Journal Article) Journal of physics. Condensed matter : an Institute of Physics journal, 21 (12), pp. 124207, 2009. @article{Kȩpa2009, title = {Interlayer coupling in EuS/SrS, EuS/PbSe and EuS/PbTe magnetic semiconductor superlattices.}, author = {Kępa, H and Majkrzak, C F and Sipatov, A.d and Fedorov, A G and Samburskaya, T A and Giebultowicz, T M}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-65449183124&partnerID=40&md5=5ed1f1e59fd3c9b80c9330bdb6f99047, http://www.ncbi.nlm.nih.gov/pubmed/21817449}, year = {2009}, date = {2009-01-01}, journal = {Journal of physics. Condensed matter : an Institute of Physics journal}, volume = {21}, number = {12}, pages = {124207}, abstract = {Neutron reflectivity studies of EuS/SrS, EuS/PbSe and EuS/PbTe all-semiconductor superlattices were carried out in a search for exchange interlayer coupling. A relatively weak antiferromagnetic coupling was found in EuS/SrS and EuS/PbSe systems but no interlayer coupling was detected in EuS/PbTe superlattices. In EuS/SrS, where the SrS spacer is an insulator (E(g)≈4 eV), a very weak and short range interlayer coupling is in agreement with the earlier theoretical predictions that the interlayer coupling strength in EuS-based magnetic semiconductor superlattices depends strongly on the energy gap of the nonmagnetic layer and should decrease with an increase of the energy gap of the spacer material. A weak coupling in EuS/PbSe and no coupling in EuS/PbTe, where both PbSe and PbTe are narrow-gap semiconductors (E(g)≈0.3 eV), is in disagreement not only with the theoretical expectations but also in stark contrast with earlier results for another narrow-gap spacer system, EuS/PbS, where pronounced antiferromagnetic coupling persists even in samples with PbS layer thicknesses as large as 200 AA. A possible influence of the increasing lattice mismatch between EuS and the spacer materials (0.5%, 0.8%, 2.5% and 8.2% for PbS, SrS, PbSe and PbTe, respectively) on the magnetic ordering of the EuS layer near the interfaces and, consequently, on the interlayer coupling is discussed.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Neutron reflectivity studies of EuS/SrS, EuS/PbSe and EuS/PbTe all-semiconductor superlattices were carried out in a search for exchange interlayer coupling. A relatively weak antiferromagnetic coupling was found in EuS/SrS and EuS/PbSe systems but no interlayer coupling was detected in EuS/PbTe superlattices. In EuS/SrS, where the SrS spacer is an insulator (E(g)≈4 eV), a very weak and short range interlayer coupling is in agreement with the earlier theoretical predictions that the interlayer coupling strength in EuS-based magnetic semiconductor superlattices depends strongly on the energy gap of the nonmagnetic layer and should decrease with an increase of the energy gap of the spacer material. A weak coupling in EuS/PbSe and no coupling in EuS/PbTe, where both PbSe and PbTe are narrow-gap semiconductors (E(g)≈0.3 eV), is in disagreement not only with the theoretical expectations but also in stark contrast with earlier results for another narrow-gap spacer system, EuS/PbS, where pronounced antiferromagnetic coupling persists even in samples with PbS layer thicknesses as large as 200 AA. A possible influence of the increasing lattice mismatch between EuS and the spacer materials (0.5%, 0.8%, 2.5% and 8.2% for PbS, SrS, PbSe and PbTe, respectively) on the magnetic ordering of the EuS layer near the interfaces and, consequently, on the interlayer coupling is discussed. |
| 46. | Fedorov, Alexander; Katrunov, Konstantin; Lalayants, Alexander; Lebedinsky, Alexey; Shiran, Natalia; Mateychenko, Pavel Properties of Vacuum Deposited CsI(Tl) and ZnSe(Te) Scintillator Layers (Journal Article) IEEE Transactions on Nuclear Science, 56 (3), pp. 955-957, 2009. @article{Fedorov2009, title = {Properties of Vacuum Deposited CsI(Tl) and ZnSe(Te) Scintillator Layers}, author = {Fedorov, Alexander and Katrunov, Konstantin and Lalayants, Alexander and Lebedinsky, Alexey and Shiran, Natalia and Mateychenko, Pavel}, url = {http://ieeexplore.ieee.org/lpdocs/epic03/wrapper.htm?arnumber=5075933}, year = {2009}, date = {2009-01-01}, journal = {IEEE Transactions on Nuclear Science}, volume = {56}, number = {3}, pages = {955-957}, abstract = {Examinations of the crystalline structure, morphology, luminescent properties of layers of vacuum deposited CsI(Tl) and ZnSe(Te) are presented. The dependence of these important features on deposition conditions is discussed. Optimized deposition conditions relying on the experimental results are proposed that allow thick columnar films to be obtained, while preserving the initial dopant content in the film.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Examinations of the crystalline structure, morphology, luminescent properties of layers of vacuum deposited CsI(Tl) and ZnSe(Te) are presented. The dependence of these important features on deposition conditions is discussed. Optimized deposition conditions relying on the experimental results are proposed that allow thick columnar films to be obtained, while preserving the initial dopant content in the film. |
| 45. | a. Klimenko, Tatyana; Ivanov, Vladimir; Adamowicz, Ludwik Dipole polarizabilities and hyperpolarizabilities of the small conjugated systems in the pi-electron coupled cluster theory (Journal Article) Molecular Physics, 107 (17), pp. 1729–1737, 2009, ISSN: 0026-8976. @article{Klimenko2009, title = {Dipole polarizabilities and hyperpolarizabilities of the small conjugated systems in the pi-electron coupled cluster theory}, author = {Klimenko, Tatyana a. and Ivanov, Vladimir V. and Adamowicz, Ludwik}, url = {http://www.tandfonline.com/doi/abs/10.1080/00268970903029123}, issn = {0026-8976}, year = {2009}, date = {2009-01-01}, journal = {Molecular Physics}, volume = {107}, number = {17}, pages = {1729--1737}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
| 44. | Volovnenko,; Tarasov,; Zubatyuk,; Shishkin,; Turov,; Volovenko, Yu. Interaction of 2-chloroquinoline- 3-carbaldehydes with 2-hetaryl- acetonitriles (Journal Article) Chemistry of Heterocyclic Compounds, 45 (12), pp. 1489-1502, 2009. @article{Volovnenko20091489, title = {Interaction of 2-chloroquinoline- 3-carbaldehydes with 2-hetaryl- acetonitriles}, author = {Volovnenko, T. A. and Tarasov, A. V. and Zubatyuk, R. I. and Shishkin, O. V. and Turov, A. V. and Volovenko, Yu. M.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-77950859085&partnerID=40&md5=6144e9694788e8151a765a89cff0f649, http://www.springerlink.com/index/10.1007/s10593-010-0456-7}, year = {2009}, date = {2009-01-01}, journal = {Chemistry of Heterocyclic Compounds}, volume = {45}, number = {12}, pages = {1489-1502}, abstract = {The interaction of 2-chloroquinoline-3-carbaldehydes with 1H-benzimidazol-2-ylacetonitriles and 1-benzyl-1H-imidazol-2-ylacetonitrile has been studied. It was shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The interaction of 2-chloroquinoline-3-carbaldehydes with 1H-benzimidazol-2-ylacetonitriles and 1-benzyl-1H-imidazol-2-ylacetonitrile has been studied. It was shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated. © 2009 Springer Science+Business Media, Inc. |
| 43. | Gorobets,; Sedash,; Shishkina,; Shishkin,; Yermolayev,; Desenko, Structure of the intermediate in the synthesis of 6-methyl-2-oxo-1,2- dihydropyridine-3-carbonitrile (Journal Article) Arkivoc, 2009 (13), pp. 23-30, 2009. @article{Gorobets200923, title = {Structure of the intermediate in the synthesis of 6-methyl-2-oxo-1,2- dihydropyridine-3-carbonitrile}, author = {Gorobets, N Y and Sedash, Y V and Shishkina, S V and Shishkin, O V and Yermolayev, S A and Desenko, S M}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-77953221760&partnerID=40&md5=9ba24298c008685e8d1f9aa380a0007b}, year = {2009}, date = {2009-01-01}, journal = {Arkivoc}, volume = {2009}, number = {13}, pages = {23-30}, abstract = {4-(Dimethylamino)but-3-en-2-one 1a reacted with malononitrile 2a affording (2E,4E)-2-cyano-5-dimethylamino)hexa-2,4-dienamide 6aa that was isolated as two isomers, 1-s-cis and 1-s-trans 6aa as confirmed by X-ray diffraction analysis. Acid-induced cyclization of 1-s-cis 6aa gave the known 1,2-dihydro-6-methyl-2- oxopyridine-3-carbonitrile 3aa, but not 1,2-dihydro-4-methyl-2-oxopyridine-3- carbonitrile 9aa as reported previously. The mechanistic pathway of the 2-pyridone ring formation is discussed.}, keywords = {}, pubstate = {published}, tppubtype = {article} } 4-(Dimethylamino)but-3-en-2-one 1a reacted with malononitrile 2a affording (2E,4E)-2-cyano-5-dimethylamino)hexa-2,4-dienamide 6aa that was isolated as two isomers, 1-s-cis and 1-s-trans 6aa as confirmed by X-ray diffraction analysis. Acid-induced cyclization of 1-s-cis 6aa gave the known 1,2-dihydro-6-methyl-2- oxopyridine-3-carbonitrile 3aa, but not 1,2-dihydro-4-methyl-2-oxopyridine-3- carbonitrile 9aa as reported previously. The mechanistic pathway of the 2-pyridone ring formation is discussed. |
| 42. | Tolkunov,; Ktyuchkov,; Zubatyuk,; Shishkin, Khimiya Geterotsiklicheskikh Soedinenii, (8), pp. 1244-1252+1280, 2009. @article{Tolkunov2009, title = {242-Cl -Benzoyl-4-methyldibenzothienyl-2)benzo[b]thienyl-31- phenyl-1-ethanone a new product of 1-methyl-3-phenylben- zothieno[2,3-c]pyrilium perchiorate interaction with nucleo philic reagents}, author = {Tolkunov, S V and Ktyuchkov, M A and Zubatyuk, R I and Shishkin, O V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70350708420&partnerID=40&md5=9cf0d34b0489080f5e16076c5cc5916c}, year = {2009}, date = {2009-01-01}, journal = {Khimiya Geterotsiklicheskikh Soedinenii}, number = {8}, pages = {1244-1252+1280}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
| 41. | Sofronov,; Kudin,; Voloshko, Yu.; Kudin,; Shishkin, Origin of the thermal desorption peaks of gases in NaI above 180°C (Journal Article) Inorganic Materials, 45 (11), pp. 1314-1318, 2009. @article{Sofronov20091314, title = {Origin of the thermal desorption peaks of gases in NaI above 180°C}, author = {Sofronov, D S and Kudin, K. A. and Voloshko, A Yu. and Kudin, A M and Shishkin, O V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70449673492&partnerID=40&md5=7f663e92e7ab860315146a3d2dc91835,, http://www.springerlink.com/index/10.1134/S0020168509110235}, year = {2009}, date = {2009-01-01}, journal = {Inorganic Materials}, volume = {45}, number = {11}, pages = {1314-1318}, abstract = {We analyze the origin of the water desorption peaks in NaI above the temperature stability range of the crystalline hydrate NaI • 2H 2O. The two water desorption peaks at t ≥ 180°C are shown to arise from the decomposition of aqua complexes based on hydroxyl groups. Such peaks in the pressure-temperature curve provide an effective and sensitive tool for detecting OH groups in raw materials. After prolonged room-temperature dehydration, no such peaks emerge. The dehydration process can be accelerated by microwave drying. © 2009 Pleiades Publishing, Ltd.}, keywords = {}, pubstate = {published}, tppubtype = {article} } We analyze the origin of the water desorption peaks in NaI above the temperature stability range of the crystalline hydrate NaI • 2H 2O. The two water desorption peaks at t ≥ 180°C are shown to arise from the decomposition of aqua complexes based on hydroxyl groups. Such peaks in the pressure-temperature curve provide an effective and sensitive tool for detecting OH groups in raw materials. After prolonged room-temperature dehydration, no such peaks emerge. The dehydration process can be accelerated by microwave drying. © 2009 Pleiades Publishing, Ltd. |
| 40. | Avdeenko,; Konovalova,; Ludchenko,; Palamarchuk,; Shishkin, Russian Journal of Organic Chemistry, 45 (11), pp. 1651-1662, 2009. @article{Avdeenko20091651, title = {Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms}, author = {Avdeenko, A. P. and Konovalova, S. A. and Ludchenko, O. N. and Palamarchuk, G. V. and Shishkin, O. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-75749128678&partnerID=40&md5=faa8185de47cfecfa7251c89661e97e8, http://www.springerlink.com/index/10.1134/S1070428009110128}, year = {2009}, date = {2009-01-01}, journal = {Russian Journal of Organic Chemistry}, volume = {45}, number = {11}, pages = {1651-1662}, abstract = {At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo-2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans- and syn-scheme. © 2009 Pleiades Publishing, Ltd.}, keywords = {}, pubstate = {published}, tppubtype = {article} } At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo-2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the trans- and syn-scheme. © 2009 Pleiades Publishing, Ltd. |
| 39. | Vreshch, Olesia; Nesterova, Oksana; Kokozay, Vladimir; Dyakonenko, Viktoriya; Shishkin, Oleg; Cormary, Benoit; Malfant, Isabelle; Jezierska, Julia Sodium Nitroprusside as a Source of Metalloligand in Direct Synthesis of Cu/Fe Complexes (Journal Article) Zeitschrift f"{u}r anorganische und allgemeine Chemie, 635 (13-14), pp. 2316-2323, 2009. @article{Vreshch20092316, title = {Sodium Nitroprusside as a Source of Metalloligand in Direct Synthesis of Cu/Fe Complexes}, author = {Vreshch, Olesia V. and Nesterova, Oksana V. and Kokozay, Vladimir N. and Dyakonenko, Viktoriya V. and Shishkin, Oleg V. and Cormary, Benoit and Malfant, Isabelle and Jezierska, Julia}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70449591318&partnerID=40&md5=877f8d8ef2eb4622eff273bf1d9afa7b, http://doi.wiley.com/10.1002/zaac.200900017}, year = {2009}, date = {2009-01-01}, journal = {Zeitschrift f"{u}r anorganische und allgemeine Chemie}, volume = {635}, number = {13-14}, pages = {2316-2323}, abstract = {This article discusses synthesis of two heterometallic complexes [Cu(phen)2Fe(CN)5(NO)]•2H2O (1) and [Cu(phen)3][Fe(CN)5(NO)]• 2H2O (2) prepared from zerovalent copper, sodium nitroprusside (SNP), ammonium thiocyanate in dimethylformamide (DMF) solution of 1,10-phenanthroline (phen). Single crystal X-ray analysis revealed that compound 1 has a molecular structure with [Cu(phen)2]2+ and [Fe(CN)5NO] 2- blocks joined through a bridging CN group of nitroprusside whereas compound 2 consists of a separate [Cu(phen)3]2+ cation and [Fe(CN)5NO]2- anion. The magnetic behaviour of compound 1 is paramagnetic. Compound 1 displays photo-induced transition to the metastable state SI after irradiation with blue light, what was proved by a low-frequency shift of v(N-O) bands. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.}, keywords = {}, pubstate = {published}, tppubtype = {article} } This article discusses synthesis of two heterometallic complexes [Cu(phen)2Fe(CN)5(NO)]•2H2O (1) and [Cu(phen)3][Fe(CN)5(NO)]• 2H2O (2) prepared from zerovalent copper, sodium nitroprusside (SNP), ammonium thiocyanate in dimethylformamide (DMF) solution of 1,10-phenanthroline (phen). Single crystal X-ray analysis revealed that compound 1 has a molecular structure with [Cu(phen)2]2+ and [Fe(CN)5NO] 2- blocks joined through a bridging CN group of nitroprusside whereas compound 2 consists of a separate [Cu(phen)3]2+ cation and [Fe(CN)5NO]2- anion. The magnetic behaviour of compound 1 is paramagnetic. Compound 1 displays photo-induced transition to the metastable state SI after irradiation with blue light, what was proved by a low-frequency shift of v(N-O) bands. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA. |
| 38. | Iminov, Rustam; Tverdokhlebov, Anton; Tolmachev, Andrey; Volovenko, Yulian; Shishkina, Svetlana; Shishkin, Oleg Synthesis of structurally constrained 4-quinazolinone derivatives with a tetrahedral C-2 atom present in three rings (Journal Article) Tetrahedron, 65 (41), pp. 8582-8586, 2009. @article{Iminov20098582, title = {Synthesis of structurally constrained 4-quinazolinone derivatives with a tetrahedral C-2 atom present in three rings}, author = {Iminov, Rustam T. and Tverdokhlebov, Anton V. and Tolmachev, Andrey A. and Volovenko, Yulian M. and Shishkina, Svetlana V. and Shishkin, Oleg V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-69749114542&partnerID=40&md5=5476768bac46a761b4fa882b108b3d2e, http://linkinghub.elsevier.com/retrieve/pii/S004040200901117X}, year = {2009}, date = {2009-01-01}, journal = {Tetrahedron}, volume = {65}, number = {41}, pages = {8582-8586}, abstract = {The reaction of 2-aminobenzamides with 2-oxocyclopentane-, 2-oxocyclohexane-, and 2-oxocycloheptaneacetic acids esters was found to give 7a,8,9,10-tetrahydrocyclopenta[2,3]pyrrolo[1,2-a]quinazoline-6,12(7H,11H )-diones, 7,7a,8,9,10,11-hexahydro-6H-indolo[1,7a-a]quinazoline-6,13(12H)-diones, and 7a,8,9,10,11,12-hexahydrocyclohepta[2,3]pyrrolo[1,2-a]quinazoline-6,14(7 H,13H)-diones, respectively. The relative configuration with the cis-fused butyrolactam and cycloalkane rings was assigned to the prepared compounds on the basis of an X-ray crystallographic study. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The reaction of 2-aminobenzamides with 2-oxocyclopentane-, 2-oxocyclohexane-, and 2-oxocycloheptaneacetic acids esters was found to give 7a,8,9,10-tetrahydrocyclopenta[2,3]pyrrolo[1,2-a]quinazoline-6,12(7H,11H )-diones, 7,7a,8,9,10,11-hexahydro-6H-indolo[1,7a-a]quinazoline-6,13(12H)-diones, and 7a,8,9,10,11,12-hexahydrocyclohepta[2,3]pyrrolo[1,2-a]quinazoline-6,14(7 H,13H)-diones, respectively. The relative configuration with the cis-fused butyrolactam and cycloalkane rings was assigned to the prepared compounds on the basis of an X-ray crystallographic study. © 2009 Elsevier Ltd. All rights reserved. |
| 37. | Shishkin, Oleg; Shtamburg, Vasiliy; Zubatyuk, Roman; Olefir, Dmitriy; Tsygankov, Alexander; Prosyanik, Alexander; Mazepa, Alexander; Kostyanovsky, Remir Chiral ureas with two electronegative substituents at 1-N: an unusual case of coexisting pyramidal and almost planar 1-N atoms in the same crystal. (Journal Article) Chirality, 21 (7), pp. 642-7, 2009. @article{Shishkin2009642, title = {Chiral ureas with two electronegative substituents at 1-N: an unusual case of coexisting pyramidal and almost planar 1-N atoms in the same crystal.}, author = {Shishkin, Oleg V and Shtamburg, Vasiliy G and Zubatyuk, Roman I and Olefir, Dmitriy A and Tsygankov, Alexander V and Prosyanik, Alexander V and Mazepa, Alexander V and Kostyanovsky, Remir G}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70349533023&partnerID=40&md5=f612150acf297c20b3b9098ab9d9f304, http://www.ncbi.nlm.nih.gov/pubmed/18979531}, year = {2009}, date = {2009-01-01}, journal = {Chirality}, volume = {21}, number = {7}, pages = {642-7}, abstract = {XRD studies of structure of N-acetoxy-N-methoxyurea and N,N-bis(methoxycarbonyl)-N-methoxyimide have revealed that in N-methoxy-N-X-ureas (X = OAc, Cl, OMe, N(+)C(5)H(5)) the additional shortening of N-OMe bond took place, which arising from an n(O(Me))-sigma*(N-X) anomeric orbital interaction. XRD studies of N-chloro-N-ethoxyurea crystal have revealed the presence of two kinds of anomeric nitrogen configuration in the O-N-Cl group in the form of a pyramidal configuration and a planar configuration for same 1-N nitrogen atom. XRD studies of N-4-chlorobenzoyloxy-N-ethoxyurea have revealed that the degree of pyramidality of the 1-N nitrogen in N-aroyloxy-N-alkoxyureas is tuned by orientation of benzoyl group with respect to the N-O bond, which in turn depends of size of N-alkoxy group.}, keywords = {}, pubstate = {published}, tppubtype = {article} } XRD studies of structure of N-acetoxy-N-methoxyurea and N,N-bis(methoxycarbonyl)-N-methoxyimide have revealed that in N-methoxy-N-X-ureas (X = OAc, Cl, OMe, N(+)C(5)H(5)) the additional shortening of N-OMe bond took place, which arising from an n(O(Me))-sigma*(N-X) anomeric orbital interaction. XRD studies of N-chloro-N-ethoxyurea crystal have revealed the presence of two kinds of anomeric nitrogen configuration in the O-N-Cl group in the form of a pyramidal configuration and a planar configuration for same 1-N nitrogen atom. XRD studies of N-4-chlorobenzoyloxy-N-ethoxyurea have revealed that the degree of pyramidality of the 1-N nitrogen in N-aroyloxy-N-alkoxyureas is tuned by orientation of benzoyl group with respect to the N-O bond, which in turn depends of size of N-alkoxy group. |
| 36. | Kosenkov, Dmytro; Kholod, Yana; Gorb, Leonid; Shishkin, Oleg; Kuramshina, Gulnara; Dovbeshko, Galina; Leszczynski, Jerzy Effect of a pH change on the conformational stability of the modified nucleotide queuosine monophosphate. (Journal Article) The journal of physical chemistry. A, 113 (33), pp. 9386-95, 2009. @article{Kosenkov20099386, title = {Effect of a pH change on the conformational stability of the modified nucleotide queuosine monophosphate.}, author = {Kosenkov, Dmytro and Kholod, Yana A and Gorb, Leonid and Shishkin, Oleg V and Kuramshina, Gulnara M and Dovbeshko, Galina I and Leszczynski, Jerzy}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70349199473&partnerID=40&md5=cea5148eff3d80b20c5c2ddc2af0cfd4, http://www.ncbi.nlm.nih.gov/pubmed/19630370}, year = {2009}, date = {2009-01-01}, journal = {The journal of physical chemistry. A}, volume = {113}, number = {33}, pages = {9386-95}, abstract = {The naturally occurring modified nucleotide queuosine 5\'-monophosphate (QMP) related to biochemical regulatory pathways in the cell was investigated using quantum chemical approaches. The relative stability of biologically relevant conformations of QMP in solvent under a pH change was predicted at the BVP86/TZVP and MP2/TZVP levels of theory. Hydrogen bonding in QMP was studied using Bader\'s approach. The acidity constants of QMP were estimated using the COSMO-RS theory. It has been found that the neutral and anionic forms of QMP are the most stable in the physiological pH range. These forms correspond to the anti/north conformation and exist as zwitterionic tautomers having a negatively charged phosphate group (-1 for neutral and -2 for anionic) and a positively charged secondary amine group in the side chain. It was also found that QMP possesses the syn conformation in the cationic state at pH < 5.0 and undergoes syn to anti conformation transition when the pH increases, remaining in the anti conformation at the higher pH values. The marker IR bands specific for the anionic and neutral QMP forms in the 2300-2700 cm(-1) region were assigned to H-bonded NH groups of the QMP side chain. The bands between 800 and 1300 cm(-1) of the \"fingerprint\" (400-1500 cm(-1)) region were assigned to the vibrations of the ribose ring, the phosphate group and the side chain of QMP. The predicted IR spectra can be useful for the assignment of vibration bands in the experiential spectra of QMP or identification of the QMP forms. The revealed peculiarities of the QMP conformation sensitivity to a pH change as well as additional formed H-bonds could be responsible for specific nucleotide interactions with enzymes.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The naturally occurring modified nucleotide queuosine 5'-monophosphate (QMP) related to biochemical regulatory pathways in the cell was investigated using quantum chemical approaches. The relative stability of biologically relevant conformations of QMP in solvent under a pH change was predicted at the BVP86/TZVP and MP2/TZVP levels of theory. Hydrogen bonding in QMP was studied using Bader's approach. The acidity constants of QMP were estimated using the COSMO-RS theory. It has been found that the neutral and anionic forms of QMP are the most stable in the physiological pH range. These forms correspond to the anti/north conformation and exist as zwitterionic tautomers having a negatively charged phosphate group (-1 for neutral and -2 for anionic) and a positively charged secondary amine group in the side chain. It was also found that QMP possesses the syn conformation in the cationic state at pH < 5.0 and undergoes syn to anti conformation transition when the pH increases, remaining in the anti conformation at the higher pH values. The marker IR bands specific for the anionic and neutral QMP forms in the 2300-2700 cm(-1) region were assigned to H-bonded NH groups of the QMP side chain. The bands between 800 and 1300 cm(-1) of the "fingerprint" (400-1500 cm(-1)) region were assigned to the vibrations of the ribose ring, the phosphate group and the side chain of QMP. The predicted IR spectra can be useful for the assignment of vibration bands in the experiential spectra of QMP or identification of the QMP forms. The revealed peculiarities of the QMP conformation sensitivity to a pH change as well as additional formed H-bonds could be responsible for specific nucleotide interactions with enzymes. |
| 35. | Moroz, Yurii; Konovalova, Irina; Iskenderov, Turganbay; Pavlova, Svetlana; Shishkin, Oleg 2-Hydroxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene]propanohydrazide. (Journal Article) Acta crystallographica. Section E, Structure reports online, 65 (Pt 9), pp. o2242, 2009. @article{Moroz2009, title = {2-Hydroxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene]propanohydrazide.}, author = {Moroz, Yurii S and Konovalova, Irina S and Iskenderov, Turganbay S and Pavlova, Svetlana V and Shishkin, Oleg V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70249139481&partnerID=40&md5=f5633165777835c588b435f35c9a117a, http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2969988&tool=pmcentrez&rendertype=abstract}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section E, Structure reports online}, volume = {65}, number = {Pt 9}, pages = {o2242}, abstract = {The title compound, C(10)H(12)N(4)O(2), features an intra-molecular N-H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds into supra-molecular zigzag chains along the c axis.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The title compound, C(10)H(12)N(4)O(2), features an intra-molecular N-H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds into supra-molecular zigzag chains along the c axis. |
| 34. | Tolkunov,; Eresko,; Khizhan,; Shishkin,; Palamarchuk,; Tolkunov, Heterocyclizations of 2-acylindolyl-3-acetic acids derivatives by hydrazine. Synthesis of 2, 3-dihydro-2-oxo-5-R1-lH-[l, 2]diazepino[4, 5-fc]indoles (Journal Article) Khimiya Geterotsiklicheskikh Soedinenii, (6), pp. 907-917+960, 2009. @article{Tolkunov2009, title = {Heterocyclizations of 2-acylindolyl-3-acetic acids derivatives by hydrazine. Synthesis of 2, 3-dihydro-2-oxo-5-R1-lH-[l, 2]diazepino[4, 5-fc]indoles}, author = {Tolkunov, V S and Eresko, A B and Khizhan, A I and Shishkin, O V and Palamarchuk, O V and Tolkunov, S V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-69549124709&partnerID=40&md5=be1e4ac811c233a0e5c6742980942105}, year = {2009}, date = {2009-01-01}, journal = {Khimiya Geterotsiklicheskikh Soedinenii}, number = {6}, pages = {907-917+960}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
| 33. | Borovskoy, Valery; Komykhov, Sergey; Musatov, Vladimir; Shishkina, Svetlana; Shishkin, Oleg; Desenko, Sergey Unusual reaction of 2-(aminomethyl)benzimidazole with chalcones: Synthesis of new aryl-substituted pyrrolines (Journal Article) Collection of Czechoslovak Chemical Communications, 74 (9), pp. 1403-1410, 2009. @article{Borovskoy20091403, title = {Unusual reaction of 2-(aminomethyl)benzimidazole with chalcones: Synthesis of new aryl-substituted pyrrolines}, author = {Borovskoy, Valery A and Komykhov, Sergey A and Musatov, Vladimir I and Shishkina, Svetlana V and Shishkin, Oleg V and Desenko, Sergey M}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-72049085507&partnerID=40&md5=bf7bd2d9c96e5f16704131c88fee86c6, http://cccc.uochb.cas.cz/74/9/1403/}, year = {2009}, date = {2009-01-01}, journal = {Collection of Czechoslovak Chemical Communications}, volume = {74}, number = {9}, pages = {1403-1410}, abstract = {The reaction of 2-(aminomethyl)benzimidazole (1) with chalcones 2a-2e leads to formation of 3,5-diaryl-2-benzimidazol-2-yl-4,5-dihydropyrroles 3a-3e. The trans orientation of benzimidazol-2-yl and 3-aryl substituents in 3a-3e was established by X-ray analysis of 3e. © 2009 Institute of Organic Chemistry and Biochemistry.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The reaction of 2-(aminomethyl)benzimidazole (1) with chalcones 2a-2e leads to formation of 3,5-diaryl-2-benzimidazol-2-yl-4,5-dihydropyrroles 3a-3e. The trans orientation of benzimidazol-2-yl and 3-aryl substituents in 3a-3e was established by X-ray analysis of 3e. © 2009 Institute of Organic Chemistry and Biochemistry. |
| 32. | Kliachyna,; Yesypenko,; Pirozhenko,; Shishkina,; Shishkin,; Boyko,; Kalchenko, Synthesis, optical resolution and absolute configuration of inherently chiral calixarene carboxylic acids (Journal Article) Tetrahedron, 65 (34), pp. 7085-7091, 2009. @article{Kliachyna20097085, title = {Synthesis, optical resolution and absolute configuration of inherently chiral calixarene carboxylic acids}, author = {Kliachyna, M.A.a and Yesypenko, O.A.a and Pirozhenko, V.V.a and Shishkina, S.V.b and Shishkin, O.V.b and Boyko, V.І. and Kalchenko, V.I.a}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67650671383&partnerID=40&md5=21dc72bea3fd741a29c495aad45d4f37, http://linkinghub.elsevier.com/retrieve/pii/S0040402009008989}, year = {2009}, date = {2009-01-01}, journal = {Tetrahedron}, volume = {65}, number = {34}, pages = {7085-7091}, abstract = {Both enantiomers of inherently chiral calixarene carboxylic acids with ABCD substitution patterns have been prepared by the benzoylation of 25-propoxy-27-(R)-N-($alpha$-phenylethyl)amidomethyloxycalix[4]arene followed by resolution of the diastereomers formed, monobromination of them and removal of the benzoyl and $alpha$-phenylethylamide auxiliary groups. The absolute configuration of the calixarenes obtained has been established by X-ray analysis. Preliminary study of the chiral recognition properties of calixarene carboxylic acid was performed. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Both enantiomers of inherently chiral calixarene carboxylic acids with ABCD substitution patterns have been prepared by the benzoylation of 25-propoxy-27-(R)-N-($alpha$-phenylethyl)amidomethyloxycalix[4]arene followed by resolution of the diastereomers formed, monobromination of them and removal of the benzoyl and $alpha$-phenylethylamide auxiliary groups. The absolute configuration of the calixarenes obtained has been established by X-ray analysis. Preliminary study of the chiral recognition properties of calixarene carboxylic acid was performed. © 2009 Elsevier Ltd. All rights reserved. |
| 31. | Shishkina, Svetlana; Shishkin, Oleg; Ukrainets, Igor; Tkach, Andrei; Grinevich, Lina Ethyl 5-[(1H-benzoimidazol-2-yl)amino-carbon-yl]-4-hydr-oxy-2-methyl-6-oxo-1-propyl-1,6-dihydro-pyridine-3-carboxyl-ate-ethanol-methanol (4/2/1). (Journal Article) Acta crystallographica. Section E, Structure reports online, 65 (Pt 8), pp. o1984, 2009. @article{Shishkina2009, title = {Ethyl 5-[(1H-benzoimidazol-2-yl)amino-carbon-yl]-4-hydr-oxy-2-methyl-6-oxo-1-propyl-1,6-dihydro-pyridine-3-carboxyl-ate-ethanol-methanol (4/2/1).}, author = {Shishkina, Svetlana V and Shishkin, Oleg V and Ukrainets, Igor V and Tkach, Andrei A and Grinevich, Lina A}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-68749086005&partnerID=40&md5=9f242468678e9109041d89641da8938a, http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2977359&tool=pmcentrez&rendertype=abstract}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section E, Structure reports online}, volume = {65}, number = {Pt 8}, pages = {o1984}, abstract = {The asymmetric unit of the title compound, 4C(20)H(22)N(4)O(5)•2C(2)H(6)O•CH(4)O, contains two pyridine-3-carboxyl-ate mol-ecules, one ethanol mol-ecule and one methanol mol-ecule disordered about in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in both independent mol-ecules are planar within 0.03 AA due to the formation of intra-molecular O-H⋯O and N-H⋯O hydrogen bonds. The formation of these latter inter-actions also causes the redistribution of the electron density within the hydroxy-pyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. In the crystal phase, the pyridine-3-carboxyl-ate mol-ecules form layers parallel to (010), which are inter-linked through hydrogen bonds mediated by the bridging solvate mol-ecules. A terminal ethyl group in one of the mol-ecules is disordered over two sites of equally occupancy.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The asymmetric unit of the title compound, 4C(20)H(22)N(4)O(5)•2C(2)H(6)O•CH(4)O, contains two pyridine-3-carboxyl-ate mol-ecules, one ethanol mol-ecule and one methanol mol-ecule disordered about in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in both independent mol-ecules are planar within 0.03 AA due to the formation of intra-molecular O-H⋯O and N-H⋯O hydrogen bonds. The formation of these latter inter-actions also causes the redistribution of the electron density within the hydroxy-pyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. In the crystal phase, the pyridine-3-carboxyl-ate mol-ecules form layers parallel to (010), which are inter-linked through hydrogen bonds mediated by the bridging solvate mol-ecules. A terminal ethyl group in one of the mol-ecules is disordered over two sites of equally occupancy. |
| 30. | Tolkunov,; Kryuchkov,; Zubatyuk,; Shishkin, Chemistry of Heterocyclic Compounds, 45 (8), pp. 990-996, 2009. @article{Tolkunov2009990, title = {2-[2-(1-benzoyl-4-methyldibenzo- thienyl-2)benzo[b]thienyl-3]phenyl- 1-ethanone – a new product of the reaction of 1-methyl-3-phenylbenzo- thieno[2,3-c]pyrilium perchlorate with nucleophilic reagents}, author = {Tolkunov, S. V. and Kryuchkov, M. A. and Zubatyuk, R. I. and Shishkin, O. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-72249096459&partnerID=40&md5=6c484a392c16fd74862cbd901c4dfd1f, http://www.springerlink.com/index/10.1007/s10593-009-0380-x}, year = {2009}, date = {2009-01-01}, journal = {Chemistry of Heterocyclic Compounds}, volume = {45}, number = {8}, pages = {990-996}, abstract = {On the interaction of 1-methyl-3-phenylbenzothieno[2,3-c]pyrilium perchlorate with primary and secondary amines and alkalis in aqueous media a product of cyclocondensation of 2-acetyl-3-phenacyl-benzo[b]thiophene - 2-[2-(1-benzoyl-4-methyldibenzothienyl-2)benzo[b]thienyl-3]phenyl-1-ethanone - was isolated in addition to the classical objects of recyclization. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } On the interaction of 1-methyl-3-phenylbenzothieno[2,3-c]pyrilium perchlorate with primary and secondary amines and alkalis in aqueous media a product of cyclocondensation of 2-acetyl-3-phenacyl-benzo[b]thiophene - 2-[2-(1-benzoyl-4-methyldibenzothienyl-2)benzo[b]thienyl-3]phenyl-1-ethanone - was isolated in addition to the classical objects of recyclization. © 2009 Springer Science+Business Media, Inc. |
| 29. | Hordiyenko, Olga; Rudenko, Igor; Biitseva, Angelina; Turov, Aleksandr; Arrault, Axelle; Brosse, Nicolas; Fabre, Olivier; Jamart-Gr'{e}goire, Brigitte; Zubatyuk, Roman; Shishkin, Oleg Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization (Journal Article) Tetrahedron, 65 (31), pp. 6218-6225, 2009. @article{Hordiyenko20096218, title = {Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization}, author = {Hordiyenko, Olga V. and Rudenko, Igor V. and Biitseva, Angelina V. and Turov, Aleksandr V. and Arrault, Axelle and Brosse, Nicolas and Fabre, Olivier and Jamart-Gr'{e}goire, Brigitte and Zubatyuk, Roman I. and Shishkin, Oleg V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67649378631&partnerID=40&md5=3239b87e2dd53e3f6a348573ad27bbb2, http://linkinghub.elsevier.com/retrieve/pii/S0040402009007558}, year = {2009}, date = {2009-01-01}, journal = {Tetrahedron}, volume = {65}, number = {31}, pages = {6218-6225}, abstract = {N′,N″-1H-Isoindole-1,3-diylidenedialkyl(aryl,heteroaryl)carbohydrazides were prepared in good yields via 1,1,3-trichloro-1H-isoindole, which was shown to be a versatile reagent for their synthesis. Tautomeric structure and conformational behaviour of dicarbohydrazides in solid state as well as in solution have been studied by X-ray crystallography, NMR spectroscopy and quantum calculations. The dependence of Z/E amide-type isomerism upon steric effects and solvent polarity is discussed. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } N′,N″-1H-Isoindole-1,3-diylidenedialkyl(aryl,heteroaryl)carbohydrazides were prepared in good yields via 1,1,3-trichloro-1H-isoindole, which was shown to be a versatile reagent for their synthesis. Tautomeric structure and conformational behaviour of dicarbohydrazides in solid state as well as in solution have been studied by X-ray crystallography, NMR spectroscopy and quantum calculations. The dependence of Z/E amide-type isomerism upon steric effects and solvent polarity is discussed. © 2009 Elsevier Ltd. All rights reserved. |
| 28. | Karpenko, Alexander; Kovalenko, Sergey; Shishkin, Oleg Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system (Journal Article) Tetrahedron, 65 (31), pp. 5964-5972, 2009. @article{Karpenko20095964, title = {Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system}, author = {Karpenko, Alexander V. and Kovalenko, Sergey I. and Shishkin, Oleg V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67649336589&partnerID=40&md5=e2e206478070c965efd55cd1cb9673b5, http://linkinghub.elsevier.com/retrieve/pii/S0040402009008400}, year = {2009}, date = {2009-01-01}, journal = {Tetrahedron}, volume = {65}, number = {31}, pages = {5964-5972}, abstract = {Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H-[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3′-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6′(1′H)-1,2,4-triazin]-5′(4′H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H-[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3′-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6′(1′H)-1,2,4-triazin]-5′(4′H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. © 2009 Elsevier Ltd. All rights reserved. |
| 27. | Tkachenko,; Tarabara,; Shishkina,; Shishkin,; Kas’yan, Amido acids of norbornene series in reactions with sulfonyl azides (Journal Article) Russian Journal of Organic Chemistry, 45 (8), pp. 1143-1148, 2009. @article{Tkachenko20091143, title = {Amido acids of norbornene series in reactions with sulfonyl azides}, author = {Tkachenko, I. V. and Tarabara, I. N. and Shishkina, S. V. and Shishkin, O. V. and Kas’yan, L. I.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70349514891&partnerID=40&md5=22cd784ca47172878175c532a1f24a5b, http://www.springerlink.com/index/10.1134/S1070428009080053}, year = {2009}, date = {2009-01-01}, journal = {Russian Journal of Organic Chemistry}, volume = {45}, number = {8}, pages = {1143-1148}, abstract = {In reaction of amido acids from the norbornene series with arenesunfonyl azides alongside the expected N,N-dialkyl-5-oxo-exo-2-arylsulfonylamino-4- oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamides (oxabrendanones) the formation of zwitter-ions with a structure of 5-(N,N-dialkyliminio)-exo-2- arylsulfonylamino-4-oxatricyclo[4.2.1.03,7]nonane-endo-9- carboxylates came as a surprise. The structure of compounds obtained was confirmed by the analysis of their IR and 1H NMR spectra. The molecular structure of one among the zwitterions was established by XRD analysis. © 2009 Pleiades Publishing, Ltd.}, keywords = {}, pubstate = {published}, tppubtype = {article} } In reaction of amido acids from the norbornene series with arenesunfonyl azides alongside the expected N,N-dialkyl-5-oxo-exo-2-arylsulfonylamino-4- oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamides (oxabrendanones) the formation of zwitter-ions with a structure of 5-(N,N-dialkyliminio)-exo-2- arylsulfonylamino-4-oxatricyclo[4.2.1.03,7]nonane-endo-9- carboxylates came as a surprise. The structure of compounds obtained was confirmed by the analysis of their IR and 1H NMR spectra. The molecular structure of one among the zwitterions was established by XRD analysis. © 2009 Pleiades Publishing, Ltd. |
| 26. | Potikha,; Kovtunenko,; Turov,; Palamarchuk,; Zubatyuk,; Shishkin., Synthesis of 2,4-diphenyl-1h- Pyrrol-1-amine derivatives (Journal Article) Khimiya Geterotsiklicheskikh Soedinenii, (3), pp. 404-414, 2009. @article{Potikha2009404, title = {Synthesis of 2,4-diphenyl-1h- Pyrrol-1-amine derivatives}, author = {Potikha, L M and Kovtunenko, V A and Turov, A V and Palamarchuk, G V and Zubatyuk, R I and Shishkin., O V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67649986727&partnerID=40&md5=f210948d2c6fafb431c8a1a936812847}, year = {2009}, date = {2009-01-01}, journal = {Khimiya Geterotsiklicheskikh Soedinenii}, number = {3}, pages = {404-414}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
| 25. | Lipson,; Karnozhitskaya,; Shishkina,; Shishkin,; Turov, Reactions of 3-amino-1,2,4-triazoles with cinnamic aldehydes (Journal Article) Russian Chemical Bulletin, 58 (7), pp. 1441-1444, 2009. @article{Lipson20091441, title = {Reactions of 3-amino-1,2,4-triazoles with cinnamic aldehydes}, author = {Lipson, V. V. and Karnozhitskaya, T. M. and Shishkina, S. V. and Shishkin, O. V. and Turov, A. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-77955720304&partnerID=40&md5=aaa0e3299d7727fdec6fbaa4db8d278e, http://www.springerlink.com/index/10.1007/s11172-009-0193-1}, year = {2009}, date = {2009-01-01}, journal = {Russian Chemical Bulletin}, volume = {58}, number = {7}, pages = {1441-1444}, abstract = {The reaction of 3-amino-and 3-amino-5-methylthio-1, 2, 4-triazoles with cinnamaldehyde takes two directions to form mixtures of 5-[JV-(3- phenylpropenylideneamino)]-1H-1, 2, 4-triazoles and 5-phenyl-4, 5, 6, 7-tetrahydro[1, 2, 4]triazolo[1, 5-a]pyrimidin-7-ols. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The reaction of 3-amino-and 3-amino-5-methylthio-1, 2, 4-triazoles with cinnamaldehyde takes two directions to form mixtures of 5-[JV-(3- phenylpropenylideneamino)]-1H-1, 2, 4-triazoles and 5-phenyl-4, 5, 6, 7-tetrahydro[1, 2, 4]triazolo[1, 5-a]pyrimidin-7-ols. © 2009 Springer Science+Business Media, Inc. |
| 24. | Shishkin, Oleg; Gorb, Leonid; Leszczynski, Jerzy Conformational flexibility of pyrimidine rings of nucleic acid bases in polar environment: PCM study (Journal Article) Structural Chemistry, 20 (4), pp. 743-749, 2009. @article{Shishkin2009743, title = {Conformational flexibility of pyrimidine rings of nucleic acid bases in polar environment: PCM study}, author = {Shishkin, Oleg V. and Gorb, Leonid and Leszczynski, Jerzy}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70349969452&partnerID=40&md5=560dd973f85a571e8fbb6a8c1900f4bb, http://www.springerlink.com/index/10.1007/s11224-009-9477-1}, year = {2009}, date = {2009-01-01}, journal = {Structural Chemistry}, volume = {20}, number = {4}, pages = {743-749}, abstract = {The results of calculations of molecular structures of nucleic acid bases in polar environment using Polarized Continuum Model of solvent combined with the MP2/cc-pvdz level of ab initio theory demonstrate considerable polarization of thymine, cytosine, and guanine. This phenomenon can be related to considerable contribution of zwitter-ionic resonant forms into total structure of the studied species. It leads to significant increase (about 30%) of frequencies of the out-of-plane pyrimidine ring vibrations and is related to considerable decrease of conformational flexibility of heterocycle due to smaller out-of-plane deformability of pyrimidine ring in zwitter-ionic resonant forms. In the case of adenine, the presence of a polar environment results in an increase of conformational flexibility of pyrimidine ring. © Springer Science+Business Media, LLC 2009.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The results of calculations of molecular structures of nucleic acid bases in polar environment using Polarized Continuum Model of solvent combined with the MP2/cc-pvdz level of ab initio theory demonstrate considerable polarization of thymine, cytosine, and guanine. This phenomenon can be related to considerable contribution of zwitter-ionic resonant forms into total structure of the studied species. It leads to significant increase (about 30%) of frequencies of the out-of-plane pyrimidine ring vibrations and is related to considerable decrease of conformational flexibility of heterocycle due to smaller out-of-plane deformability of pyrimidine ring in zwitter-ionic resonant forms. In the case of adenine, the presence of a polar environment results in an increase of conformational flexibility of pyrimidine ring. © Springer Science+Business Media, LLC 2009. |
| 23. | Ukrainets, Igor; Shishkina, Svetlana; Shishkin, Oleg; Davidenko, Alexandra; Tkach, Andrei Ethyl 2-(4-hydr-oxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)acetate. (Journal Article) Acta crystallographica. Section E, Structure reports online, 65 (Pt 5), pp. o968, 2009. @article{Ukrainets2009, title = {Ethyl 2-(4-hydr-oxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)acetate.}, author = {Ukrainets, Igor V and Shishkina, Svetlana V and Shishkin, Oleg V and Davidenko, Alexandra A and Tkach, Andrei A}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-66749152687&partnerID=40&md5=8f48c5f9a94749f0d3a56a71da7dfa74, http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2977667&tool=pmcentrez&rendertype=abstract}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section E, Structure reports online}, volume = {65}, number = {Pt 5}, pages = {o968}, abstract = {In the title compound, C(14)H(15)NO(4), the bicyclic fragment and the ester group form a dihedral angle of 86.7 (2)°. Inter-molecular O-H⋯O and C-H⋯O hydrogen bonding connects mol-ecules into a helix along the crystallographic b axis.}, keywords = {}, pubstate = {published}, tppubtype = {article} } In the title compound, C(14)H(15)NO(4), the bicyclic fragment and the ester group form a dihedral angle of 86.7 (2)°. Inter-molecular O-H⋯O and C-H⋯O hydrogen bonding connects mol-ecules into a helix along the crystallographic b axis. |
| 22. | Beznischenko, Asya; Makhankova, Valeriya; Kokozay, Vladimir; Dyakonenko, Viktoriya; Shishkin, Oleg Direct synthesis of Co/Mn complex with Co-semisepulchrate entity (Journal Article) Inorganic Chemistry Communications, 12 (6), pp. 473-475, 2009. @article{Beznischenko2009473, title = {Direct synthesis of Co/Mn complex with Co-semisepulchrate entity}, author = {Beznischenko, Asya O. and Makhankova, Valeriya G. and Kokozay, Vladimir N. and Dyakonenko, Viktoriya V. and Shishkin, Oleg V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67349168417&partnerID=40&md5=3d4c8986dda914196b429c30cbbd15a7, http://linkinghub.elsevier.com/retrieve/pii/S1387700309001853}, year = {2009}, date = {2009-01-01}, journal = {Inorganic Chemistry Communications}, volume = {12}, number = {6}, pages = {473-475}, abstract = {A novel compound [CoL][Mn(ox)2]Cl•3H2O [L - N(CH2NHC2H4NH2)3, tris(((aminoethyl)amino)methyl)amine] (1), has been synthesized and structurally characterized. The compound 1 represents a new and rare example constructed by 1D polymeric [Mn (ox)2]n2 n - anions and semisepulchrate [CoIIIL]3+ cations. An efficient and simple procedure for the synthesis of 1 has been proposed. The advantages of this procedure include: one pot reaction, good efficiency and easily available starting materials. © 2009 Elsevier B.V. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A novel compound [CoL][Mn(ox)2]Cl•3H2O [L - N(CH2NHC2H4NH2)3, tris(((aminoethyl)amino)methyl)amine] (1), has been synthesized and structurally characterized. The compound 1 represents a new and rare example constructed by 1D polymeric [Mn (ox)2]n2 n - anions and semisepulchrate [CoIIIL]3+ cations. An efficient and simple procedure for the synthesis of 1 has been proposed. The advantages of this procedure include: one pot reaction, good efficiency and easily available starting materials. © 2009 Elsevier B.V. All rights reserved. |
| 21. | Pivnenko, Nikolay; Turov, Alexander; Abakumov, Vladimir; Kutulya, Lidiya; Shishkina, Svetlana; Shishkin, Oleg Molecular structures of regioisomeric 7-arylidene hexahydroindazoles from (1)H NMR spectra. (Journal Article) Magnetic resonance in chemistry : MRC, 47 (6), pp. 488-96, 2009. @article{Pivnenko2009488, title = {Molecular structures of regioisomeric 7-arylidene hexahydroindazoles from (1)H NMR spectra.}, author = {Pivnenko, Nikolay S and Turov, Alexander V and Abakumov, Vladimir V and Kutulya, Lidiya A and Shishkina, Svetlana V and Shishkin, Oleg V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67049174161&partnerID=40&md5=36993333ae84f9917ae199beef29bb2d, http://www.ncbi.nlm.nih.gov/pubmed/19267426}, year = {2009}, date = {2009-01-01}, journal = {Magnetic resonance in chemistry : MRC}, volume = {47}, number = {6}, pages = {488-96}, abstract = {The structural characterization of two regioisomeric products of the interaction of 2,6-bis-(4-methoxybenzylidene)-3R-methylcyclohexanone with methyl hydrazine was achieved using (1)H NMR spectral data, including chemical shifts, coupling constants and results of COSY and nuclear overhauser effect (NOE) experiments. Configurations of the new chiral centers in the (3S,3aR,6R,7E)-7-(4-methoxybenzylidene)-3,4,5,7-hexahydro-3-(4-methoxyphenyl)-2,6-dimethyl- and 2,4-dimethyl-2H-indazoles were assigned on the basis of experimental data combined with molecular modeling by the density functional theory (DFT) method. The distinction in the helical twisting power of studied compounds under addition to a nematic liquid crystal is discussed on the basis of peculiarities of the molecular structures.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The structural characterization of two regioisomeric products of the interaction of 2,6-bis-(4-methoxybenzylidene)-3R-methylcyclohexanone with methyl hydrazine was achieved using (1)H NMR spectral data, including chemical shifts, coupling constants and results of COSY and nuclear overhauser effect (NOE) experiments. Configurations of the new chiral centers in the (3S,3aR,6R,7E)-7-(4-methoxybenzylidene)-3,4,5,7-hexahydro-3-(4-methoxyphenyl)-2,6-dimethyl- and 2,4-dimethyl-2H-indazoles were assigned on the basis of experimental data combined with molecular modeling by the density functional theory (DFT) method. The distinction in the helical twisting power of studied compounds under addition to a nematic liquid crystal is discussed on the basis of peculiarities of the molecular structures. |
| 20. | Tolkunov,; Eresko,; Khizhan,; Shishkin,; Palamarchuk,; Tolkunov, Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles (Journal Article) Chemistry of Heterocyclic Compounds, 45 (6), pp. 726-734, 2009. @article{Tolkunov2009726, title = {Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles}, author = {Tolkunov, V. S. and Eresko, A. B. and Khizhan, A. I. and Shishkin, O. V. and Palamarchuk, G. V. and Tolkunov, S. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-70350183745&partnerID=40&md5=4edd736ba11a22bf7e9171da1bceef00, http://www.springerlink.com/index/10.1007/s10593-009-0322-7}, year = {2009}, date = {2009-01-01}, journal = {Chemistry of Heterocyclic Compounds}, volume = {45}, number = {6}, pages = {726-734}, abstract = {The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate. © 2009 Springer Science+Business Media, Inc. |
| 19. | Boyko,; Matvieiev, Yu.I.a; Klyachina,; Yesypenko,; Shishkina,; Shishkin,; Kalchenko, Proximal heteroalkylation of monoalkoxycalix[4]arenes in synthesis of inherently chiral molecules (Journal Article) Tetrahedron, 65 (21), pp. 4220-4227, 2009. @article{Boyko20094220, title = {Proximal heteroalkylation of monoalkoxycalix[4]arenes in synthesis of inherently chiral molecules}, author = {Boyko, V.I.a and Matvieiev, Yu.I.a and Klyachina, M.A.a and Yesypenko, O.A.a and Shishkina, S.V.b and Shishkin, O.V. and Kalchenko, V.I.a}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-64649088571&partnerID=40&md5=fa8061ed2ab7551bf70bd1a662502599, http://linkinghub.elsevier.com/retrieve/pii/S0040402009004141}, year = {2009}, date = {2009-01-01}, journal = {Tetrahedron}, volume = {65}, number = {21}, pages = {4220-4227}, abstract = {Proximal heteroalkylation of monoalkyl ethers of calix[4]arenes or p-tert-butylcalix[4]arenes in NaH/CH 3CN or NaOH/DMSO, respectively, was applied for synthesis of inherently chiral calixarenes with ABHH substitution pattern. The introduction by the method of (R)- or (S)-N-($alpha$-phenylethyl)acetamide chiral auxiliary group gives mixtures of diastereomeric derivatives of inherently chiral calixarenes, which were separated by column chromatography. The chiral calixarenes were thoroughly characterized by 1H, 13C NMR, and X-ray diffraction methods. © 2009.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Proximal heteroalkylation of monoalkyl ethers of calix[4]arenes or p-tert-butylcalix[4]arenes in NaH/CH 3CN or NaOH/DMSO, respectively, was applied for synthesis of inherently chiral calixarenes with ABHH substitution pattern. The introduction by the method of (R)- or (S)-N-($alpha$-phenylethyl)acetamide chiral auxiliary group gives mixtures of diastereomeric derivatives of inherently chiral calixarenes, which were separated by column chromatography. The chiral calixarenes were thoroughly characterized by 1H, 13C NMR, and X-ray diffraction methods. © 2009. |
| 18. | Nikitina, Vitalina; Nesterova, Oksana; Kokozay, Vladimir; Zubatyuk, Roman; Dyakonenko, Viktoriya; Shishkin, Oleg; Goreshnik, Evgeny; G'{o}mez-Garc'{i}a, Carlos; Clemente-Juan, Juan; Jezierska, Julia Supramolecular diversity and magnetic properties of novel heterometallic Cu(II)/Cr(III) complexes prepared from copper powder, Reineckes salt and ethylenediamine (Journal Article) Inorganica Chimica Acta, 362 (7), pp. 2237-2246, 2009. @article{Nikitina20092237, title = {Supramolecular diversity and magnetic properties of novel heterometallic Cu(II)/Cr(III) complexes prepared from copper powder, Reineckes salt and ethylenediamine}, author = {Nikitina, Vitalina M. and Nesterova, Oksana V. and Kokozay, Vladimir N. and Zubatyuk, Roman I. and Dyakonenko, Viktoriya V. and Shishkin, Oleg V. and Goreshnik, Evgeny A. and G'{o}mez-Garc'{i}a, Carlos J. and Clemente-Juan, Juan M. and Jezierska, Julia}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67349263033&partnerID=40&md5=b3c89f091d7575ec6b5f824685a43952, http://linkinghub.elsevier.com/retrieve/pii/S0020169308006257}, year = {2009}, date = {2009-01-01}, journal = {Inorganica Chimica Acta}, volume = {362}, number = {7}, pages = {2237-2246}, abstract = {Three novel heterometallic complexes [Cu(en)2Cr(NCS)4(NH3)2][Cr(N CS)4(NH3)2] • 6dmf (1), [Cu(en)2Cr(NCS)4(NH3)2](OAc) (2) and [{Cu(en)2}3{Cr(NCS)4(NH3) 2}2(NCS)2](NCS)2 (3) have been synthesized in a one-pot reaction from copper powder, Reineckes salt, NH4X [X- = OAc- (2), NCS- (3)] in a dmf (1) or CH3CN (2, 3) solution of ethylenediamine (en). X-ray studies showed that 1 and 2 consist of cationic polymeric chains, formed by Cu (en)22 + and Cr (NCS)4 (NH3)2- building blocks that bridged through thiocyanate anions. In both complexes, distinct hydrogen bonds are present and serve to increase the dimensionality of the compound from one to two (in 1) or three (in 2). The main structural feature of 3 is the pentanuclear Cu3Cr2 cation which is H-bonded with uncoordinated thiocyanate groups generating a 3D supramolecular assembly. The shortest Cu⋯Cr distances are 5.840(1) AA for 1, 5.856(1) and 6.018(3) AA for 2 and 6.009(9) and 6.465(9) AA for 3. Compounds 1 and 2 are essentially paramagnets whereas compound 3 shows a weak antiferromagnetic coupling. The magnetic properties are simulated and discussed in terms of the structural features. © 2008 Elsevier B.V. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Three novel heterometallic complexes [Cu(en)2Cr(NCS)4(NH3)2][Cr(N CS)4(NH3)2] • 6dmf (1), [Cu(en)2Cr(NCS)4(NH3)2](OAc) (2) and [{Cu(en)2}3{Cr(NCS)4(NH3) 2}2(NCS)2](NCS)2 (3) have been synthesized in a one-pot reaction from copper powder, Reineckes salt, NH4X [X- = OAc- (2), NCS- (3)] in a dmf (1) or CH3CN (2, 3) solution of ethylenediamine (en). X-ray studies showed that 1 and 2 consist of cationic polymeric chains, formed by Cu (en)22 + and Cr (NCS)4 (NH3)2- building blocks that bridged through thiocyanate anions. In both complexes, distinct hydrogen bonds are present and serve to increase the dimensionality of the compound from one to two (in 1) or three (in 2). The main structural feature of 3 is the pentanuclear Cu3Cr2 cation which is H-bonded with uncoordinated thiocyanate groups generating a 3D supramolecular assembly. The shortest Cu⋯Cr distances are 5.840(1) AA for 1, 5.856(1) and 6.018(3) AA for 2 and 6.009(9) and 6.465(9) AA for 3. Compounds 1 and 2 are essentially paramagnets whereas compound 3 shows a weak antiferromagnetic coupling. The magnetic properties are simulated and discussed in terms of the structural features. © 2008 Elsevier B.V. All rights reserved. |
| 17. | Moroz, Olesia; Trush, Victor; Konovalova, Irina; Shishkin, Oleg; Moroz, Yurii; Demeshko, Serhiy; Amirkhanov, Vladimir New copper(II) 1D polymer containing dimethyl(phenylsulfonyl)amidophosphate: Synthesis, crystal structure and magnetic properties (Journal Article) Polyhedron, 28 (7), pp. 1331-1335, 2009. @article{Moroz20091331, title = {New copper(II) 1D polymer containing dimethyl(phenylsulfonyl)amidophosphate: Synthesis, crystal structure and magnetic properties}, author = {Moroz, Olesia V. and Trush, Victor A. and Konovalova, Irina S. and Shishkin, Oleg V. and Moroz, Yurii S. and Demeshko, Serhiy and Amirkhanov, Vladimir M.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-64549092795&partnerID=40&md5=aa9fbcd38df54e7bee91678a818042b5, http://linkinghub.elsevier.com/retrieve/pii/S0277538709000886}, year = {2009}, date = {2009-01-01}, journal = {Polyhedron}, volume = {28}, number = {7}, pages = {1331-1335}, abstract = {The reaction of sodium dimethyl(phenylsulfonyl)amidophosphate NaL (HL = C 6H 5SO 2NHP(O)(OCH 3) 2) with Cu(NO 3) 2 • 6H 2O and o-bpe (1,2-bis(pyridine-2-yl)ethane) in appropriate ratios, afford the formation of 1D coordination polymer [Cu(L) 2 • o-bpe] n in good yield. The crystal structures of HL (1) and [Cu(L) 2 • o-bpe] n (2) are reported. In the crystal package the molecules of 1 are linked by intermolecular hydrogen bonds formed by the phosphoryl oxygen atoms which serve as acceptors and nitrogen atoms of amide groups as donors. The crystal structure of 2 indicates the presence of unsaturated Cu(L) 2 unit bridged by o-bpe ligand in the one-dimensional polymeric chain. The Cu(II) atoms have distorted 4 + 2 octahedral CuO 4N 2 environment formed by the oxygen atoms belonging to the sulfonyl and phosphoryl groups of two deprotonated chelate ligands and nitrogen atoms of the bridging o-bpe ligands. The magnetic study of 2 has revealed the presence of a weak intrachain antiferromagnetic exchange interaction between copper ions. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The reaction of sodium dimethyl(phenylsulfonyl)amidophosphate NaL (HL = C 6H 5SO 2NHP(O)(OCH 3) 2) with Cu(NO 3) 2 • 6H 2O and o-bpe (1,2-bis(pyridine-2-yl)ethane) in appropriate ratios, afford the formation of 1D coordination polymer [Cu(L) 2 • o-bpe] n in good yield. The crystal structures of HL (1) and [Cu(L) 2 • o-bpe] n (2) are reported. In the crystal package the molecules of 1 are linked by intermolecular hydrogen bonds formed by the phosphoryl oxygen atoms which serve as acceptors and nitrogen atoms of amide groups as donors. The crystal structure of 2 indicates the presence of unsaturated Cu(L) 2 unit bridged by o-bpe ligand in the one-dimensional polymeric chain. The Cu(II) atoms have distorted 4 + 2 octahedral CuO 4N 2 environment formed by the oxygen atoms belonging to the sulfonyl and phosphoryl groups of two deprotonated chelate ligands and nitrogen atoms of the bridging o-bpe ligands. The magnetic study of 2 has revealed the presence of a weak intrachain antiferromagnetic exchange interaction between copper ions. © 2009 Elsevier Ltd. All rights reserved. |
| 16. | Nikitina, Vitalina; Nesterova, Oksana; Kokozay, Vladimir; Dyakonenko, Viktoriya; Shishkin, Oleg; Jezierska, Julia N,N-Dimethylethylenediamine in direct and direct template syntheses of Cu(II)/Cr(III) complexes (Journal Article) Polyhedron, 28 (7), pp. 1265-1272, 2009. @article{Nikitina20091265, title = {N,N-Dimethylethylenediamine in direct and direct template syntheses of Cu(II)/Cr(III) complexes}, author = {Nikitina, Vitalina M. and Nesterova, Oksana V. and Kokozay, Vladimir N. and Dyakonenko, Viktoriya V. and Shishkin, Oleg V. and Jezierska, Julia}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-64549093257&partnerID=40&md5=f998b67ee641296302287ece098f44fe, http://linkinghub.elsevier.com/retrieve/pii/S0277538709001582}, year = {2009}, date = {2009-01-01}, journal = {Polyhedron}, volume = {28}, number = {7}, pages = {1265-1272}, abstract = {Four new heterometallic Cu(II)/Cr(III) complexes with N,N-dimethylethylenediamine (dmen) and its novel Schiff-base derivatives, N′-[(1Z)-3-amino-1,3-dimethylbutylidene]-N,N-dimethylethane-1,2-diamine (dmenac) and N′-((1Z)-3-{[2-(dimethylamino)ethyl]amino}-1,3-dimethylbutylidene)-N,N-dimethylethane-1,2-diamine (dmen2ac), have been easily prepared by self-assembly and characterized by spectroscopic methods and single crystal X-ray analysis. The structures of all the complexes are assisted by numerous hydrogen bonds that provide a web of interactions and mould the supramolecular architectures of the compounds. Variable-temperature (1.8-300 K) magnetic susceptibility measurements reveal Curie-Weiss paramagnetic behavior of all the compounds, supported by EPR studies. © 2009 Elsevier Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Four new heterometallic Cu(II)/Cr(III) complexes with N,N-dimethylethylenediamine (dmen) and its novel Schiff-base derivatives, N′-[(1Z)-3-amino-1,3-dimethylbutylidene]-N,N-dimethylethane-1,2-diamine (dmenac) and N′-((1Z)-3-{[2-(dimethylamino)ethyl]amino}-1,3-dimethylbutylidene)-N,N-dimethylethane-1,2-diamine (dmen2ac), have been easily prepared by self-assembly and characterized by spectroscopic methods and single crystal X-ray analysis. The structures of all the complexes are assisted by numerous hydrogen bonds that provide a web of interactions and mould the supramolecular architectures of the compounds. Variable-temperature (1.8-300 K) magnetic susceptibility measurements reveal Curie-Weiss paramagnetic behavior of all the compounds, supported by EPR studies. © 2009 Elsevier Ltd. All rights reserved. |
| 15. | Dzhavakhishvili, Sergey; Gorobets, Nikolay Yu; Shishkina, Svetlana; Shishkin, Oleg; Desenko, Sergey; Groth, Ulrich Diversification of a thieno[2,3-d]pyrimidin-4-one scaffold via regioselective alkylation reactions. (Journal Article) Journal of combinatorial chemistry, 11 (3), pp. 508-14, 2009. @article{Dzhavakhishvili2009508, title = {Diversification of a thieno[2,3-d]pyrimidin-4-one scaffold via regioselective alkylation reactions.}, author = {Dzhavakhishvili, Sergey G and Gorobets, Nikolay Yu and Shishkina, Svetlana V and Shishkin, Oleg V and Desenko, Sergey M and Groth, Ulrich M}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-66149152157&partnerID=40&md5=53ec52c18b90d3a93831dc3ea8465144, http://www.ncbi.nlm.nih.gov/pubmed/19385601}, year = {2009}, date = {2009-01-01}, journal = {Journal of combinatorial chemistry}, volume = {11}, number = {3}, pages = {508-14}, abstract = {The 2-aryl-2,3,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4(1H)-ones and 2-aryl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-ones have been diversified by alkylation reactions, applying benzylchlorides and N-substituted 2-chloroacetamides as alkylating agents. Under the found uniform conditions the substitution direction does not depend on the structure of the alkylating agent and gives monoalkylated products in high yields with simple workup. The alkylation of the 2,3-dihydropyrimidin-4(1H)-one derivatives proceeds onto the N1-position; however, in the case of pyrimidin-4(3H)-ones the O-alkylated products are formed selectively. An alternative strategy for the synthesis of the N1-benzyl-2,3-dihydropyrimidin-4(1H)-one derivatives is also developed. It applies the redaction of N2-substituted Gewald\'s amides with aromatic aldehydes and allows simple introduction of various substituents in the final molecule.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The 2-aryl-2,3,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4(1H)-ones and 2-aryl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-ones have been diversified by alkylation reactions, applying benzylchlorides and N-substituted 2-chloroacetamides as alkylating agents. Under the found uniform conditions the substitution direction does not depend on the structure of the alkylating agent and gives monoalkylated products in high yields with simple workup. The alkylation of the 2,3-dihydropyrimidin-4(1H)-one derivatives proceeds onto the N1-position; however, in the case of pyrimidin-4(3H)-ones the O-alkylated products are formed selectively. An alternative strategy for the synthesis of the N1-benzyl-2,3-dihydropyrimidin-4(1H)-one derivatives is also developed. It applies the redaction of N2-substituted Gewald's amides with aromatic aldehydes and allows simple introduction of various substituents in the final molecule. |
| 14. | Avdeenko,; Konovalova,; Sergeeva,; Palamarchuk,; Shishkin, Reaction of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone monoimines with alcohols (Journal Article) Russian Journal of Organic Chemistry, 45 (5), pp. 674-680, 2009. @article{Avdeenko2009674, title = {Reaction of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone monoimines with alcohols}, author = {Avdeenko, A. P. and Konovalova, S. A. and Sergeeva, A. G. and Palamarchuk, G. V. and Shishkin, O. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67049142544&partnerID=40&md5=08efd87b16de903a53451c633f5dbbc3, http://www.springerlink.com/index/10.1134/S1070428009050054}, year = {2009}, date = {2009-01-01}, journal = {Russian Journal of Organic Chemistry}, volume = {45}, number = {5}, pages = {674-680}, abstract = {Reactions of N-alkyl(aryl)aminocarbonyl-3,5-dimethyl-1,4-benzoquinone monoimines with alcohols led to the formation of products of 1,2-addition, quinolide compounds. They are the final products in reactions with alkyl derivatives, but in event of aryl derivatives they underwent cyclization with the subsequent elimination of the alcohol molecule to provide 4,7a-dimethyl-1-aryl-7,7a-dihydro-1H-benzimidazole-2,6-diones. © 2009 Pleiades Publishing, Ltd.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Reactions of N-alkyl(aryl)aminocarbonyl-3,5-dimethyl-1,4-benzoquinone monoimines with alcohols led to the formation of products of 1,2-addition, quinolide compounds. They are the final products in reactions with alkyl derivatives, but in event of aryl derivatives they underwent cyclization with the subsequent elimination of the alcohol molecule to provide 4,7a-dimethyl-1-aryl-7,7a-dihydro-1H-benzimidazole-2,6-diones. © 2009 Pleiades Publishing, Ltd. |
| 13. | Tarasov, Andrii; Volovnenko, Tatyana; Zubatyuk, Roman; Shishkin, Oleg; Volovenko, Yulian 14-(2,3-Dichloro-phen-yl)-9,10-dimethyl-benzimidazo[1,2-a]benzo[f][1,8]naphthyridine-6-carbonitrile. (Journal Article) Acta crystallographica. Section E, Structure reports online, 65 (Pt 4), pp. o792, 2009. @article{Tarasov2009, title = {14-(2,3-Dichloro-phen-yl)-9,10-dimethyl-benzimidazo[1,2-a]benzo[f][1,8]naphthyridine-6-carbonitrile.}, author = {Tarasov, Andrii V and Volovnenko, Tatyana A and Zubatyuk, Roman I and Shishkin, Oleg V and Volovenko, Yulian M}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-64149132378&partnerID=40&md5=d95ea1509f1306c078cbd60c6d435802, http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2969033&tool=pmcentrez&rendertype=abstract}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section E, Structure reports online}, volume = {65}, number = {Pt 4}, pages = {o792}, abstract = {In the title compound, C(27)H(16)Cl(2)N(4), the benzimidazo[1,2-a]benzo[f][1,8]naphthyridine system is nearly planar (r.m.s. deviation for all non-H atoms = 0.033 AA). The dichloro-phenyl substituent is rotated by -67.5 (2)° from this plane. In the crystal structure, mol-ecules form stacks along the crystallographic (100) direction due to $pi$-$pi$ stacking inter-actions with a centroid-centroid distance of 3.4283 (9) AA.}, keywords = {}, pubstate = {published}, tppubtype = {article} } In the title compound, C(27)H(16)Cl(2)N(4), the benzimidazo[1,2-a]benzo[f][1,8]naphthyridine system is nearly planar (r.m.s. deviation for all non-H atoms = 0.033 AA). The dichloro-phenyl substituent is rotated by -67.5 (2)° from this plane. In the crystal structure, mol-ecules form stacks along the crystallographic (100) direction due to $pi$-$pi$ stacking inter-actions with a centroid-centroid distance of 3.4283 (9) AA. |
| 12. | Tverdokhlebov, Anton; Denisenko, Alexander; Tolmachev, Andrey; Volovenko, Yulian; Shishkina, Svetlana; Shishkin, Oleg Synthesis of Masked Vicinal Amino Aldehydes of Pyrrolizine and Pyrrolo [1,2-c]thiazole Series (Journal Article) Synthesis, 2009 (08), pp. 1265-1270, 2009. @article{Tverdokhlebov20091265, title = {Synthesis of Masked Vicinal Amino Aldehydes of Pyrrolizine and Pyrrolo [1,2-c]thiazole Series}, author = {Tverdokhlebov, Anton and Denisenko, Alexander and Tolmachev, Andrey and Volovenko, Yulian and Shishkina, Svetlana and Shishkin, Oleg}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67650072479&partnerID=40&md5=7929fdbf35211dde1c1cd98ae997dbaa, http://www.thieme-connect.de/DOI/DOI?10.1055/s-0028-1088029}, year = {2009}, date = {2009-01-01}, journal = {Synthesis}, volume = {2009}, number = {08}, pages = {1265-1270}, abstract = {Acylation of (1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-ylidene) acetonitrile with mixed anhydrides of N-Boc proline and 4-thiazolidinecarboxylic acid was found to proceed at the exocyclic carbon atom yielding the corresponding C-acyl derivatives. Removal of the protecting group with equimolar amount of hydrochloric acid effected simultaneous cyclization affording 2-(3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizin-2-yl)- and 2-(5-amino-7,7a-dihydro-7-oxo-1H,3H-pyrrolo[1,2-c]thiazol-6-yl)-1, 3-dimethylbenzimidazolium chlorides. Reduction of the prepared salts with sodium borohydride resulted in 3-amino-2-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2- yl)-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one and 5-amino-6-(2,3-dihydro-1,3- dimethyl-1H-benzimidazol-2-yl)-1,7a-dihydro-3H,7H-pyrrolo[1,2-c]thiazol-7-one, respectively. These compounds were shown to be masked aldehydes. Their reactions with phenylhydrazine and hydroxylamine yielded corresponding hydrazones and oximes, whereas condensation with malononitrile furnished 2-amino-5a,6,7,8- tetrahydro-5-oxo-5H-pyrido[3,2-b]pyrrolizine-3-carbonitrile and 2-amino-5a,6-dihydro-5H,8H-thiazolo[3′,4′:1,5]pyrrolo[2,3-b] pyridine-3-carbonitrile. © Georg Thieme Verlag Stuttgart.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Acylation of (1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-ylidene) acetonitrile with mixed anhydrides of N-Boc proline and 4-thiazolidinecarboxylic acid was found to proceed at the exocyclic carbon atom yielding the corresponding C-acyl derivatives. Removal of the protecting group with equimolar amount of hydrochloric acid effected simultaneous cyclization affording 2-(3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizin-2-yl)- and 2-(5-amino-7,7a-dihydro-7-oxo-1H,3H-pyrrolo[1,2-c]thiazol-6-yl)-1, 3-dimethylbenzimidazolium chlorides. Reduction of the prepared salts with sodium borohydride resulted in 3-amino-2-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2- yl)-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one and 5-amino-6-(2,3-dihydro-1,3- dimethyl-1H-benzimidazol-2-yl)-1,7a-dihydro-3H,7H-pyrrolo[1,2-c]thiazol-7-one, respectively. These compounds were shown to be masked aldehydes. Their reactions with phenylhydrazine and hydroxylamine yielded corresponding hydrazones and oximes, whereas condensation with malononitrile furnished 2-amino-5a,6,7,8- tetrahydro-5-oxo-5H-pyrido[3,2-b]pyrrolizine-3-carbonitrile and 2-amino-5a,6-dihydro-5H,8H-thiazolo[3′,4′:1,5]pyrrolo[2,3-b] pyridine-3-carbonitrile. © Georg Thieme Verlag Stuttgart. |
| 11. | Muravyova, Elena; Shishkina, Svetlana; Musatov, Vladimir; Knyazeva, Irina; Shishkin, Oleg; Desenko, Sergey; Chebanov, Valentin Chemoselectivity of Multicomponent Condensations of Barbituric Acids, 5-Aminopyrazoles, and Aldehydes (Journal Article) Synthesis, 2009 (08), pp. 1375-1385, 2009. @article{Muravyova20091375, title = {Chemoselectivity of Multicomponent Condensations of Barbituric Acids, 5-Aminopyrazoles, and Aldehydes}, author = {Muravyova, Elena and Shishkina, Svetlana and Musatov, Vladimir and Knyazeva, Irina and Shishkin, Oleg and Desenko, Sergey and Chebanov, Valentin}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67650072566&partnerID=40&md5=5a186f12bc7bea813131ac70833aa4f7, http://www.thieme-connect.de/DOI/DOI?10.1055/s-0028-1088024}, year = {2009}, date = {2009-01-01}, journal = {Synthesis}, volume = {2009}, number = {08}, pages = {1375-1385}, abstract = {Multicomponent cyclocondensations between 5-aminopyrazoles, barbituric acids, and aromatic aldehydes under conventional thermal heating, microwave irradiation, or ultrasonic irradiation were studied and the temperature regime was found to be the main factor in controlling their chemoselectivity. At high temperatures the starting materials react in two different ways yielding pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines or their dihydro analogues depending on the nature of the N-substituent in the 5-aminopyrazole. Treatment at room temperature results in a new fourcomponent reaction giving previously undisclosed heterocyclic compounds, 4,6-diaryl-1,4,6,7-tetrahydro- 2′H-spiro[pyrazolo[3,4-b]pyridine-5,5′-pyrimidine]s. Facile multipurpose three-component selective procedures to new spiroheterocycles are proposed. © Georg Thieme Verlag Stuttgart.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Multicomponent cyclocondensations between 5-aminopyrazoles, barbituric acids, and aromatic aldehydes under conventional thermal heating, microwave irradiation, or ultrasonic irradiation were studied and the temperature regime was found to be the main factor in controlling their chemoselectivity. At high temperatures the starting materials react in two different ways yielding pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines or their dihydro analogues depending on the nature of the N-substituent in the 5-aminopyrazole. Treatment at room temperature results in a new fourcomponent reaction giving previously undisclosed heterocyclic compounds, 4,6-diaryl-1,4,6,7-tetrahydro- 2′H-spiro[pyrazolo[3,4-b]pyridine-5,5′-pyrimidine]s. Facile multipurpose three-component selective procedures to new spiroheterocycles are proposed. © Georg Thieme Verlag Stuttgart. |
| 10. | b e Palamarchuk,; b c e Shishkin,; c d e Gorb,; c e Leszczynski, Dependence of deformability of geometries and characteristics of intramolecular hydrogen bonds in canonical 2′-deoxyribonucleotides on DNA conformations (Journal Article) Journal of Biomolecular Structure and Dynamics, 26 (5), pp. 653-661, 2009. @article{Palamarchuk2009653, title = {Dependence of deformability of geometries and characteristics of intramolecular hydrogen bonds in canonical 2′-deoxyribonucleotides on DNA conformations}, author = {Palamarchuk, G.V.a b e and Shishkin, O.V.a b c e and Gorb, L.b c d e and Leszczynski, J.b c e}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-66949117548&partnerID=40&md5=5c0d9b04db450f76082d2ad92cd93425}, year = {2009}, date = {2009-01-01}, journal = {Journal of Biomolecular Structure and Dynamics}, volume = {26}, number = {5}, pages = {653-661}, abstract = {The molecular structure and deformability (with respect to average geometry) of methyl ethers of canonical 2′-deoxyribonucleotides thymidine-5′-phosphate (mTMP), 2-deoxycytidine-5′-phosphate (mCMP), 2-deoxyadenosine-5′-phosphate (mAMP) and 2′-deoxyguanosine-5′- phosphate (mGMP) in different types of DNA have been calculated using B3LYP/cc-pvdz method. Comparison of energy at equilibrium conformations of nucleotides and conformations with torsion angles of backbone fixed to average values for different types of DNA reveals that incorporation of nucleotides to A-DNA macromolecules requires the minimum amount of deformation energy. Therefore, this type of DNA should be the least strained from viewpoint of intramolecular deformations of monomers. Modeling of environmental effects within the PCM approach reveals that the immersion of nucleotides in polar medium results in significant decrease of energy differences between anti conformers of all DNTs and syn conformers of mGMP. This also leads to reduction by almost a half nucleotides\' deformation energy facilitating formation of DNA macromolecule. Change of DNTs conformation causes switch between different types of intramolecular H bonds. Every type of DNA possesses unique set of intramolecular hydrogen bonds in nucleotides. ©Adenine Press (2009).}, keywords = {}, pubstate = {published}, tppubtype = {article} } The molecular structure and deformability (with respect to average geometry) of methyl ethers of canonical 2′-deoxyribonucleotides thymidine-5′-phosphate (mTMP), 2-deoxycytidine-5′-phosphate (mCMP), 2-deoxyadenosine-5′-phosphate (mAMP) and 2′-deoxyguanosine-5′- phosphate (mGMP) in different types of DNA have been calculated using B3LYP/cc-pvdz method. Comparison of energy at equilibrium conformations of nucleotides and conformations with torsion angles of backbone fixed to average values for different types of DNA reveals that incorporation of nucleotides to A-DNA macromolecules requires the minimum amount of deformation energy. Therefore, this type of DNA should be the least strained from viewpoint of intramolecular deformations of monomers. Modeling of environmental effects within the PCM approach reveals that the immersion of nucleotides in polar medium results in significant decrease of energy differences between anti conformers of all DNTs and syn conformers of mGMP. This also leads to reduction by almost a half nucleotides' deformation energy facilitating formation of DNA macromolecule. Change of DNTs conformation causes switch between different types of intramolecular H bonds. Every type of DNA possesses unique set of intramolecular hydrogen bonds in nucleotides. ©Adenine Press (2009). |
| 9. | Zubatyuk, Roman; Shishkin, Oleg; Gorb, Leonid; Leszczynski, Jerzy The journal of physical chemistry. A, 113 (12), pp. 2943-52, 2009. @article{Zubatyuk20092943, title = {Homonuclear versus heteronuclear resonance-assisted hydrogen bonds: tautomerism, aromaticity, and intramolecular hydrogen bonding in heterocyclic systems with different exocyclic proton donor/acceptor.}, author = {Zubatyuk, Roman I and Shishkin, Oleg V and Gorb, Leonid and Leszczynski, Jerzy}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-63849198123&partnerID=40&md5=80b5d7157471ffdb5e85dd63562d481f, http://www.ncbi.nlm.nih.gov/pubmed/19296712}, year = {2009}, date = {2009-01-01}, journal = {The journal of physical chemistry. A}, volume = {113}, number = {12}, pages = {2943-52}, abstract = {Tautomerism and resonance-assisted hydrogen bonding have been analyzed on the basis of the results of ab initio calculations at the MP2/AUG-cc-pVDZ level of theory for the series of molecules containing different heterocycles connected with resonance spacer and containing different exocyclic proton donor/acceptor atoms. It is demonstrated that the position of tautomeric equilibrium is controlled mainly by two factors: aromaticity of heterocycle, which could be different for two tautomers, and relative proton affinities of two heteroatoms forming a hydrogen bond. Replacement of exocyclic proton donor/acceptor atom results in change of an aromaticity degree of heterocycle leading to alteration of relative stability of tautomers. Comparison of structure and properties of E and Z conformers of molecules demonstrates resonance-assisted character of intramolecular hydrogen bond. Application of the NBO theory reveals that the pi-component of the electron density within resonant spacer plays the primary role for determination of characteristics of hydrogen bond while sigma-skeleton only reflects the pi-polarization. An analysis of strength of intramolecular hydrogen bond using geometrical, energetic, and AIM and NBO parameters indicates that the homonuclear N...H-N hydrogen bond is considerably weaker than heteronuclear N...H-O and N...H-S hydrogen bonds in the case of the XH tautomers.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Tautomerism and resonance-assisted hydrogen bonding have been analyzed on the basis of the results of ab initio calculations at the MP2/AUG-cc-pVDZ level of theory for the series of molecules containing different heterocycles connected with resonance spacer and containing different exocyclic proton donor/acceptor atoms. It is demonstrated that the position of tautomeric equilibrium is controlled mainly by two factors: aromaticity of heterocycle, which could be different for two tautomers, and relative proton affinities of two heteroatoms forming a hydrogen bond. Replacement of exocyclic proton donor/acceptor atom results in change of an aromaticity degree of heterocycle leading to alteration of relative stability of tautomers. Comparison of structure and properties of E and Z conformers of molecules demonstrates resonance-assisted character of intramolecular hydrogen bond. Application of the NBO theory reveals that the pi-component of the electron density within resonant spacer plays the primary role for determination of characteristics of hydrogen bond while sigma-skeleton only reflects the pi-polarization. An analysis of strength of intramolecular hydrogen bond using geometrical, energetic, and AIM and NBO parameters indicates that the homonuclear N...H-N hydrogen bond is considerably weaker than heteronuclear N...H-O and N...H-S hydrogen bonds in the case of the XH tautomers. |
| 8. | Palamarchuk,; Borisov,; Kovalenko,; Chernykh,; Kovalenko,; Baumer,; Shishkin, 1-(8-Bromo-2-methyl-4-thioxo-3,4,5,6-tetra-hydro-2H-2,6-methano-1,3-benzoxazocin-11-yl)ethanone. (Journal Article) Acta crystallographica. Section E, Structure reports online, 65 (Pt 3), pp. o461, 2009. @article{Palamarchuk2009, title = {1-(8-Bromo-2-methyl-4-thioxo-3,4,5,6-tetra-hydro-2H-2,6-methano-1,3-benzoxazocin-11-yl)ethanone.}, author = {Palamarchuk, G V and Borisov, O V and Kovalenko, S S and Chernykh, V P and Kovalenko, S M and Baumer, V N and Shishkin, O V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-62149129731&partnerID=40&md5=24e8f212b7c7bf2acd5a88fb7aecb1df, http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2968576&tool=pmcentrez&rendertype=abstract}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section E, Structure reports online}, volume = {65}, number = {Pt 3}, pages = {o461}, abstract = {In the title compound, C(14)H(14)BrNO(2)S, there are two similar non-equivalent mol-ecules in the asymmetric unit, displaying three chiral centres each. In the crystal structure, they are linked by inter-molecular N-H⋯O hydrogen bonds to form infinite chains, which are in turn connected by weak Br⋯H and S⋯H inter-actions.}, keywords = {}, pubstate = {published}, tppubtype = {article} } In the title compound, C(14)H(14)BrNO(2)S, there are two similar non-equivalent mol-ecules in the asymmetric unit, displaying three chiral centres each. In the crystal structure, they are linked by inter-molecular N-H⋯O hydrogen bonds to form infinite chains, which are in turn connected by weak Br⋯H and S⋯H inter-actions. |
| 7. | Beznischenko, Asya; Makhankova, Valeriya; Kokozay, Vladimir; Dyakonenko, Viktoriya; Zubatyuk, Roman; Shishkin, Oleg; Jezierska, Julia as a source of manganese in the direct synthesis of heterobimetallic Cu/Mn complexes (Journal Article) Inorganica Chimica Acta, 362 (4), pp. 1307-1314, 2009. @article{Beznischenko20091307, title = {as a source of manganese in the direct synthesis of heterobimetallic Cu/Mn complexes}, author = {Beznischenko, Asya O. and Makhankova, Valeriya G. and Kokozay, Vladimir N. and Dyakonenko, Viktoriya V. and Zubatyuk, Roman I. and Shishkin, Oleg V. and Jezierska, Julia}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-59649121538&partnerID=40&md5=7bcf6d7929c75b4f701b089326faf724, http://linkinghub.elsevier.com/retrieve/pii/S002016930800457X}, year = {2009}, date = {2009-01-01}, journal = {Inorganica Chimica Acta}, volume = {362}, number = {4}, pages = {1307-1314}, abstract = {{Complexes [Cu(en)2MnCl4] • Solv [en = ethylenediamine}, keywords = {}, pubstate = {published}, tppubtype = {article} } {Complexes [Cu(en)2MnCl4] • Solv [en = ethylenediamine |
| 6. | Potikha,; Kovtunenko,; Turov,; Palamarchuk,; Zubatyuk,; Shishkin, Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives (Journal Article) Chemistry of Heterocyclic Compounds, 45 (3), pp. 327-335, 2009. @article{Potikha2009327, title = {Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives}, author = {Potikha, L. M. and Kovtunenko, V. A. and Turov, A. V. and Palamarchuk, G. V. and Zubatyuk, R. I. and Shishkin, O. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-67651225125&partnerID=40&md5=745fee2dd9fcc55165bd32b60e6df801, http://www.springerlink.com/index/10.1007/s10593-009-0269-8}, year = {2009}, date = {2009-01-01}, journal = {Chemistry of Heterocyclic Compounds}, volume = {45}, number = {3}, pages = {327-335}, abstract = {The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one ($gamma$-bromodypnone) with hydrazines depends on the nature of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. $gamma$-Bromodypnone and phenylhydrazine give both 1,3,5-triphenyl-1,4-dihydropyridazine and N,2,4-triphenyl-1H-pyrrol-1-amine (15%). 1-(2,4-Dinitrophenyl)hydrazine gives the 2,4-dinitrophenylhydrazone of (Z)-4-bromo-1,3-diphenyl-2-buten-1-one. Condensation of 2,4-diphenyl-1H-pyrrol-1-amine with aromatic aldehydes readily leads to N-(arylmethylidene)-2,4-diphenyl-1H-pyrrol-1-amines and alkylation with methyl iodide gives N,N-dimethyl-2,4-diphenyl-1H-pyrrol-1-amine. © 2009 Springer Science+Business Media, Inc.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one ($gamma$-bromodypnone) with hydrazines depends on the nature of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. $gamma$-Bromodypnone and phenylhydrazine give both 1,3,5-triphenyl-1,4-dihydropyridazine and N,2,4-triphenyl-1H-pyrrol-1-amine (15%). 1-(2,4-Dinitrophenyl)hydrazine gives the 2,4-dinitrophenylhydrazone of (Z)-4-bromo-1,3-diphenyl-2-buten-1-one. Condensation of 2,4-diphenyl-1H-pyrrol-1-amine with aromatic aldehydes readily leads to N-(arylmethylidene)-2,4-diphenyl-1H-pyrrol-1-amines and alkylation with methyl iodide gives N,N-dimethyl-2,4-diphenyl-1H-pyrrol-1-amine. © 2009 Springer Science+Business Media, Inc. |
| 5. | Nikitina, Vitalina; Nesterova, Oksana; Kokozay, Vladimir; Dyakonenko, Viktoriya; Shishkin, Oleg; Jezierska, Julia Novel heterometallic Cu(II)/Cr(III) complex with unique open-chain N-ligand produced in conditions of direct template synthesis (Journal Article) Inorganic Chemistry Communications, 12 (2), pp. 101-104, 2009. @article{Nikitina2009101, title = {Novel heterometallic Cu(II)/Cr(III) complex with unique open-chain N-ligand produced in conditions of direct template synthesis}, author = {Nikitina, Vitalina M. and Nesterova, Oksana V. and Kokozay, Vladimir N. and Dyakonenko, Viktoriya V. and Shishkin, Oleg V. and Jezierska, Julia}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-58749097410&partnerID=40&md5=4eabef751663125ddc695c4251cd637c, http://linkinghub.elsevier.com/retrieve/pii/S1387700308004267}, year = {2009}, date = {2009-01-01}, journal = {Inorganic Chemistry Communications}, volume = {12}, number = {2}, pages = {101-104}, abstract = {The one-pot self-assembly reaction of copper powder, Reineckes salt, acetone and tris(2-aminoethyl)amine (tren) in dmso affords to obtain a heterometallic compound [Cu(trenac)][Cr(NCS)4(NH3)2](NCS) • 6dmso with novel Schiff-base ligand N-(2-{[(1E)-3-amino-1,3-dimethylbutylidene]amino}ethyl)-N-(2-aminoethyl)ethane-1,2-diamine (trenac). The ligand trenac is generated by metal-directed condensation of tren, acetone and ammonia, formed during the synthetic procedure. X-ray structural investigations showed that the complex consists of [Cu(trenac)]2+ cations, anions of the Reineckes salt [Cr(NCS)4(NH3)2]-, uncoordinated thiocyanate groups and dmso molecules, which are held together by electrostatic forces and hydrogen-bonded interactions. The compound was characterized by EPR spectroscopic and magnetic susceptibility measurements. © 2008 Elsevier B.V. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The one-pot self-assembly reaction of copper powder, Reineckes salt, acetone and tris(2-aminoethyl)amine (tren) in dmso affords to obtain a heterometallic compound [Cu(trenac)][Cr(NCS)4(NH3)2](NCS) • 6dmso with novel Schiff-base ligand N-(2-{[(1E)-3-amino-1,3-dimethylbutylidene]amino}ethyl)-N-(2-aminoethyl)ethane-1,2-diamine (trenac). The ligand trenac is generated by metal-directed condensation of tren, acetone and ammonia, formed during the synthetic procedure. X-ray structural investigations showed that the complex consists of [Cu(trenac)]2+ cations, anions of the Reineckes salt [Cr(NCS)4(NH3)2]-, uncoordinated thiocyanate groups and dmso molecules, which are held together by electrostatic forces and hydrogen-bonded interactions. The compound was characterized by EPR spectroscopic and magnetic susceptibility measurements. © 2008 Elsevier B.V. All rights reserved. |
| 4. | Shishkin, Oleg; Zubatyuk, Roman; Zhovtyak, Oleg Yu.; Kiriyak, Andrey; Kotlyar, Sergei; Kamalov, Gerbert Unexpected 3:2 stoichiometry and structure of 15-crown-5 complex with lithium chlorochromate (Journal Article) Structural Chemistry, 20 (1), pp. 139-143, 2009. @article{Shishkin2009139, title = {Unexpected 3:2 stoichiometry and structure of 15-crown-5 complex with lithium chlorochromate}, author = {Shishkin, Oleg V. and Zubatyuk, Roman I. and Zhovtyak, Oleg Yu. and Kiriyak, Andrey V. and Kotlyar, Sergei A. and Kamalov, Gerbert L.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-60349088378&partnerID=40&md5=3ba0a6ef4524c4d9790c9da47fc6ba37, http://www.springerlink.com/index/10.1007/s11224-008-9388-6}, year = {2009}, date = {2009-01-01}, journal = {Structural Chemistry}, volume = {20}, number = {1}, pages = {139-143}, abstract = {X-ray diffraction study of the lithium chlorochromate complex with 15-crown-5 (15C5) revealed the existence of an unexpected complex dication with [(15C5)3Li2(H2O)2]2+ composition, which is also stable in the gas phase according to the quantum-chemical calculations by B3LYP/6-311+G(d,p) method. © 2008 Springer Science+Business Media, LLC.}, keywords = {}, pubstate = {published}, tppubtype = {article} } X-ray diffraction study of the lithium chlorochromate complex with 15-crown-5 (15C5) revealed the existence of an unexpected complex dication with [(15C5)3Li2(H2O)2]2+ composition, which is also stable in the gas phase according to the quantum-chemical calculations by B3LYP/6-311+G(d,p) method. © 2008 Springer Science+Business Media, LLC. |
| 3. | Shishkin, Oleg; Konovalova, Irina; Gorb, Leonid; Leszczynski, Jerzy Novel type of mixed O–H•••N/O–H•••$pi$ hydrogen bonds: monohydrate of pyridine (Journal Article) Structural Chemistry, 20 (1), pp. 37-41, 2009. @article{Shishkin200937, title = {Novel type of mixed O–H•••N/O–H•••$pi$ hydrogen bonds: monohydrate of pyridine}, author = {Shishkin, Oleg V. and Konovalova, Irina S. and Gorb, Leonid and Leszczynski, Jerzy}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-60349083545&partnerID=40&md5=1636ef49e9455e5291cb9d652ec99322, http://www.springerlink.com/index/10.1007/s11224-009-9412-5}, year = {2009}, date = {2009-01-01}, journal = {Structural Chemistry}, volume = {20}, number = {1}, pages = {37-41}, abstract = {Investigation of characteristics of hydrogen bonding between pyridine and water by MP2/aug-cc-pvdz method reveals that these two molecules may form three types of hydrogen bonds depending on nature of proton withdrawal site of pyridine. Change of orientation of water with respect to plane of aromatic ring leads to transformation of the O-H⋯N bond to O-H⋯$pi$ bond via wide region of the potential energy surface where both lone pair of the nitrogen atom and $pi$-system make significant contribution into hydrogen bonding. Hydrogen bond in this intermediate region may be considered as mixed O-H⋯N/O-H⋯$pi$ bond representing new type of H bonds. © 2009 Springer Science+Business Media, LLC.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Investigation of characteristics of hydrogen bonding between pyridine and water by MP2/aug-cc-pvdz method reveals that these two molecules may form three types of hydrogen bonds depending on nature of proton withdrawal site of pyridine. Change of orientation of water with respect to plane of aromatic ring leads to transformation of the O-H⋯N bond to O-H⋯$pi$ bond via wide region of the potential energy surface where both lone pair of the nitrogen atom and $pi$-system make significant contribution into hydrogen bonding. Hydrogen bond in this intermediate region may be considered as mixed O-H⋯N/O-H⋯$pi$ bond representing new type of H bonds. © 2009 Springer Science+Business Media, LLC. |
| 2. | Shishkina, Svetlana; Zubatyuk, Roman; Kucherenko, Lyudmila; Mazur, Ivan; Shishkin, Oleg Two polymorphs of morpholin-4-ium 2-(5-methyl-1H-1,2,4-triazol-3-ylsulfanyl)acetate. (Journal Article) Acta crystallographica. Section C, Crystal structure communications, 65 (Pt 1), pp. o24-6, 2009. @article{Shishkina2009, title = {Two polymorphs of morpholin-4-ium 2-(5-methyl-1H-1,2,4-triazol-3-ylsulfanyl)acetate.}, author = {Shishkina, Svetlana V and Zubatyuk, Roman I and Kucherenko, Lyudmila I and Mazur, Ivan A and Shishkin, Oleg V}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-58149528977&partnerID=40&md5=6bafeab0c991f1841df1fc1d33171be0, http://www.ncbi.nlm.nih.gov/pubmed/19129604}, year = {2009}, date = {2009-01-01}, journal = {Acta crystallographica. Section C, Crystal structure communications}, volume = {65}, number = {Pt 1}, pages = {o24-6}, abstract = {Two polymorphs of the title organic salt (a very effective medicinal preparation with the commercial name thiotriazoline), C(4)H(10)NO(+).C(5)H(6)N(3)O(2)S(-), were obtained. The cations and anions are connected by hydrogen bonds and extend into two-dimensional networks. The main packing motifs are an R(4)(4)(12) cluster in the monoclinic form and a chain in the orthorhombic form.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Two polymorphs of the title organic salt (a very effective medicinal preparation with the commercial name thiotriazoline), C(4)H(10)NO(+).C(5)H(6)N(3)O(2)S(-), were obtained. The cations and anions are connected by hydrogen bonds and extend into two-dimensional networks. The main packing motifs are an R(4)(4)(12) cluster in the monoclinic form and a chain in the orthorhombic form. |
| 1. | Avdeenko,; Konovalova,; Roman’kov,; Burmistrov,; Nichvoloda,; Shishkin,; Zubatyuk,; Palamarchuk, Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids (Journal Article) Russian Journal of Organic Chemistry, 45 (1), pp. 48-67, 2009. @article{Avdeenko200948, title = {Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids}, author = {Avdeenko, A. P. and Konovalova, S. A. and Roman’kov, D. A. and Burmistrov, K. S. and Nichvoloda, V. M. and Shishkin, O. V. and Zubatyuk, R. I. and Palamarchuk, G. V.}, url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-60849114754&partnerID=40&md5=e068a98fd68ad308857c7d43e41f23cc, http://www.springerlink.com/index/10.1134/S1070428009010084}, year = {2009}, date = {2009-01-01}, journal = {Russian Journal of Organic Chemistry}, volume = {45}, number = {1}, pages = {48-67}, abstract = {The regioselectivity in the reactions of N-arylsulfonyl-2,6-dialkyl-1,4- benzoquinone imines with arenesulfinic acids (1,6-, 6,1-, or 6,3-addition) is determined by steric factor, while in the reactions of N-aroyl-1,4-benzoquinone imines electronic effect of substituents in the quinoid ring is crucial. The reactions of N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinone imines with arenesulfinic acids follow mainly the 1,4-addition pattern. N-(N- Arylsulfonylbenzimidoyl)-1,4-benzoquinone imines are capable of reacting in a way similar to both N-arylsulfonyl and N-aroyl derivatives. © 2009 Pleiades Publishing, Ltd.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The regioselectivity in the reactions of N-arylsulfonyl-2,6-dialkyl-1,4- benzoquinone imines with arenesulfinic acids (1,6-, 6,1-, or 6,3-addition) is determined by steric factor, while in the reactions of N-aroyl-1,4-benzoquinone imines electronic effect of substituents in the quinoid ring is crucial. The reactions of N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinone imines with arenesulfinic acids follow mainly the 1,4-addition pattern. N-(N- Arylsulfonylbenzimidoyl)-1,4-benzoquinone imines are capable of reacting in a way similar to both N-arylsulfonyl and N-aroyl derivatives. © 2009 Pleiades Publishing, Ltd. |
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