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RESEARCH PRODUCT
Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones
Ghazwan F. FadhilM. SamalikovaKatri LaihiaAlexander PerjéssyHanan A. RadhyErkki KolehmainenZora ŠUstekováWalter M. F. Fabiansubject
StereochemistrySubstituentPharmaceutical ScienceField effectArticleAnalytical Chemistry3-dioneslcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistry5-Substituted indole-23-dionesDrug DiscoveryAtomAM1 and PM3 theoretical dataπ-polarizationWavenumberPhysical and Theoretical ChemistrySpectral dataIndole testreverse substituent effectChemistryChemical shiftOrganic ChemistryIR and NMR data DSP correlationsChemistry (miscellaneous)5-Substituted indole-2Molecular MedicinePhysical chemistryÀ-polarizationRotational–vibrational couplingdescription
Correlations of AM1 and PM3 theoretical data, 13C-NMR substituent chemical shifts (13C-SCS) and IR carbonyl group wave numbers [ν(C3â•ÂO)] 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 À-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(C3â•ÂO) and p(C3â•ÂO) 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-11-01 | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |