TY  - JOUR
A1  - Baranac-Stojanovic, Marija
A1  - Klaumuenzer, Ute
A1  - Markovic, Rade
A1  - Kleinpeter, Erich
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
N2  - 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.
Y1  - 2010
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/32057
UR  - http://www.sciencedirect.com/science/journal/00404020
SN  - 0040-4020
ER  -