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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
Authors
Baranac-Stojanović, Marija
Klaumuenzer, Ute
Marković, Rade
Kleinpeter, Erich
Article (Published version)
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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.
Keywords:
Push-pull effect / 2-Alkylidene-4-thiazolidinones / Ab initio MO calculation / NBO analysis / NMR spectroscopy
Source:
Tetrahedron, 2010, 66, 46, 8958-8967
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • 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
[ Google Scholar ]
17
16
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3172
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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 . .

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