Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium

被引：5

作者：

Martyniak, Agata ^{[1
]}

Lipkowski, Pawel ^{[2
]}

Boens, Noel ^{[3
]}

Filarowski, Aleksander ^{[1
]}

机构：

[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland

[2] Wroclaw Univ Technol, Inst Phys & Theoret Chem, Theoret Chem Grp, PL-50370 Wroclaw, Poland

[3] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium

来源：

JOURNAL OF MOLECULAR MODELING | 2012年 / 18卷 / 01期

关键词：

Aromaticity; Carbonylamine; Enolimine; Intramolecular hydrogen bond; QTAIM; Tautomeric equilibrium; HOMA; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; INTRAMOLECULAR PROTON-TRANSFER; MOLECULAR-ORBITAL METHODS; HYDROGEN-BOND STRENGTH; KETO-ENOL EQUILIBRIA; SCHIFF-BASES; H-BOND; BASIS-SETS; AB-INITIO; RESONANCE;

D O I：

10.1007/s00894-011-1075-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The ketoenamine-enolimine tautometic equilibrium has been studied by the analysis of aromaticity and electron-topological parameters. The influence of substituents on the energy of the transition state and of the tautomeric forms has been investigated for different positions of chelate chain. The quantum theory of atoms in molecules method (QTAIM) has been applied to study changes in the electron-topological parameters of the molecule with respect to the tautomeric equilibrium in intramolecular hydrogen bond. Dependencies of the HOMA aromaticity index and electron density at the critical points defining aromaticity and electronic state of the chelate chain on the transition state (TS), OH and HN tautomeric forms have been obtained.

引用

页码：257 / 263

页数：7

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