Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives
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2010
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Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Structures of a series of push-pull 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives were optimized at the B3LYP/6-31G(d) level of theory in the gas phase and discussed with respect to configurational and conformational stability. Employing the GIAO method, C-13 NMR chemical shifts of the C-2, C-2', C-4 and C-5 atoms were calculated at the same level of theory in the gas phase and with inclusion of solvent, and compared with experimental data. Push-pull effect of all compounds was quantified by means of the quotient pi*/pi, length of the partial double bond, C-13 NMR chemical shift difference (Delta delta(C=C)) and H-1 NMR chemical shifts of olefinic protons. The effect of bromine on donating and accepting ability of other substituents of the push-pull C=C double bond is discussed, too. (C) 2010 Elsevier Ltd. All rights reserved.
Ključne reči:
Push-pull effect / 2-Alkylidene-4-thiazolidinones / Ab initio MO calculation / NBO analysis / NMR spectroscopyIzvor:
Tetrahedron, 2010, 66, 46, 8958-8967Izdavač:
- Oxford : Pergamon-Elsevier Science Ltd
Finansiranje / projekti:
- Deutscher Akademischer Austauschdienst (DAAD) [504 252 70]
- Ministry of Science of the Republic of Serbia
DOI: 10.1016/j.tet.2010.09.040
ISSN: 0040-4020
WoS: 000284499100023
Scopus: 2-s2.0-77958195188
Institucija/grupa
IHTMTY - JOUR AU - Baranac-Stojanović, Marija AU - Klaumuenzer, Ute AU - Marković, Rade AU - Kleinpeter, Erich PY - 2010 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3172 AB - Structures of a series of push-pull 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives were optimized at the B3LYP/6-31G(d) level of theory in the gas phase and discussed with respect to configurational and conformational stability. Employing the GIAO method, C-13 NMR chemical shifts of the C-2, C-2', C-4 and C-5 atoms were calculated at the same level of theory in the gas phase and with inclusion of solvent, and compared with experimental data. Push-pull effect of all compounds was quantified by means of the quotient pi*/pi, length of the partial double bond, C-13 NMR chemical shift difference (Delta delta(C=C)) and H-1 NMR chemical shifts of olefinic protons. The effect of bromine on donating and accepting ability of other substituents of the push-pull C=C double bond is discussed, too. (C) 2010 Elsevier Ltd. All rights reserved. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron T1 - Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives VL - 66 IS - 46 SP - 8958 EP - 8967 DO - 10.1016/j.tet.2010.09.040 ER -
@article{ author = "Baranac-Stojanović, Marija and Klaumuenzer, Ute and Marković, Rade and Kleinpeter, Erich", year = "2010", abstract = "Structures of a series of push-pull 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives were optimized at the B3LYP/6-31G(d) level of theory in the gas phase and discussed with respect to configurational and conformational stability. Employing the GIAO method, C-13 NMR chemical shifts of the C-2, C-2', C-4 and C-5 atoms were calculated at the same level of theory in the gas phase and with inclusion of solvent, and compared with experimental data. Push-pull effect of all compounds was quantified by means of the quotient pi*/pi, length of the partial double bond, C-13 NMR chemical shift difference (Delta delta(C=C)) and H-1 NMR chemical shifts of olefinic protons. The effect of bromine on donating and accepting ability of other substituents of the push-pull C=C double bond is discussed, too. (C) 2010 Elsevier Ltd. All rights reserved.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron", title = "Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives", volume = "66", number = "46", pages = "8958-8967", doi = "10.1016/j.tet.2010.09.040" }
Baranac-Stojanović, M., Klaumuenzer, U., Marković, R.,& Kleinpeter, E.. (2010). Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives. in Tetrahedron Oxford : Pergamon-Elsevier Science Ltd., 66(46), 8958-8967. https://doi.org/10.1016/j.tet.2010.09.040
Baranac-Stojanović M, Klaumuenzer U, Marković R, Kleinpeter E. Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives. in Tetrahedron. 2010;66(46):8958-8967. doi:10.1016/j.tet.2010.09.040 .
Baranac-Stojanović, Marija, Klaumuenzer, Ute, Marković, Rade, Kleinpeter, Erich, "Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives" in Tetrahedron, 66, no. 46 (2010):8958-8967, https://doi.org/10.1016/j.tet.2010.09.040 . .