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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Authors: | Marija Baranac-Stojanovi? Ute Klaumünzer Erich Kleinpeter |
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Institution: | a Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, 11000 Belgrade, Serbia b Center for Chemistry ICTM, PO Box 473, 11000 Belgrade, Serbia c Chemisches Institut der Universität Potsdam, Karl-Liebknecht Str.24-25, D-14476 Potsdam (Golm), Germany |
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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, 13C 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 π∗/π, length of the partial double bond, 13C NMR chemical shift difference (ΔδC C) and 1H 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. |
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Keywords: | Push-pull effect 2-Alkylidene-4-thiazolidinones Ab initio MO calculation NBO analysis NMR spectroscopy |
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