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Molecules 2002, 7(11), 833-839; doi:10.3390/71100833
Article

Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones

1, 1, 2,* , 2, 3, 4, 3 and 2
1 Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq 2 Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK - 842 15 Bratislava, Slovak Republic 3 Department of Chemistry, University of Jyväskylä, FIN - 40351 Jyväskylä, Finland 4 Institute of Chemistry, Karl Franzens University, A - 8010 Graz, Austria
* Author to whom correspondence should be addressed.
Received: 20 May 2002 / Revised: 5 November 2002 / Accepted: 27 November 2002 / Published: 30 November 2002
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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 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.

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