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RESEARCH PRODUCT

Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons

Renato ContrerasRenato ContrerasRaquel CastilloPatricia PérezLuis R. DomingoJuan Andrés

subject

Carbon atomChemistryChemical shiftOrganic ChemistrySubstituentcarbonyl derivativecarbonylCarbon-13 NMRcarbon nuclear magnetic resonancePhotochemistryDFT calculationsBiochemistryMedicinal chemistryParrReaction rateElectron-withdrawing effectschemistry.chemical_compoundElectronegativityDrug DiscoveryElectrophilePolar effectChemical Reactivityphenylacetic acid derivativeElectrophilicityGround state

description

Indexación: Scopus The substituent effects on the carbonyl carbon atom for a series of twelve substituted phenyl acetates have been rationalized using a global electrophilicity index. This index is linearly correlated with the experimental reaction rate coefficients. We found that, in contrast to the proposed interpretation based on experimental 13C NMR chemical shifts and ground state destabilization calculations, the electrophilicity of carbonyl compounds increases due to the effect promoted by electron-withdrawing groups in these systems. https://www.sciencedirect.com/science/article/pii/S0040402004018046?via%3Dihub

yearjournalcountryeditionlanguage
2005-01-01
10.1016/j.tet.2004.10.085