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Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones
Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK - 842 15 Bratislava, Slovak Republic
Department of Chemistry, University of Jyväskylä, FIN - 40351 Jyväskylä, Finland
Institute of Chemistry, Karl Franzens University, A - 8010 Graz, Austria
* Author to whom correspondence should be addressed.
Received: 20 May 2002; in revised form: 5 November 2002 / Accepted: 27 November 2002 / Published: 30 November 2002
Abstract: Correlations of AM1 and PM3 theoretical data, 13C-NMR substituent chemical shifts (13C-SCS) and IR carbonyl group wave numbers [ν(C3═O)] were studied using dual substituent parameter (DSP) models for 5-substituted indole-2,3-diones. For the C7 atom a reverse substituent effect attributed to extended π-polarization was observed. On the other hand, the DSP approaches for the C3 atom showed normal substituent effects with some contribution of reverse effect supported strongly by 13C-SCS correlations. In the ν(C3═O) and p(C3═O) DSP correlations the field effect contribution predominates over the resonance effect, which justifies the using of earlier suggested vibrational coupling (V-C) model for 5- and 6-substituted indole-2,3-diones.
Keywords: 5-Substituted indole-2; 3-diones; AM1 and PM3 theoretical data; IR and NMR data DSP correlations; π-polarization; reverse substituent effect
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Fadhil, G.F.; Radhy, H.A.; Perjéssy, A.; Šamalíková, M.; Kolehmainen, E.; Fabian, W.M.; Laihia, K.; Šusteková, Z. Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones. Molecules 2002, 7, 833-839.
Fadhil GF, Radhy HA, Perjéssy A, Šamalíková M, Kolehmainen E, Fabian WM, Laihia K, Šusteková Z. Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones. Molecules. 2002; 7(11):833-839.
Fadhil, Ghazwan F.; Radhy, Hanan A.; Perjéssy, Alexander; Šamalíková, Mária; Kolehmainen, Erkki; Fabian, Walter M.; Laihia, Katri; Šusteková, Zora. 2002. "Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones." Molecules 7, no. 11: 833-839.