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Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium
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 qu...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer-Verlag
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3249559/ https://www.ncbi.nlm.nih.gov/pubmed/21523531 http://dx.doi.org/10.1007/s00894-011-1075-7 |
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author | Martyniak, Agata Lipkowski, Pawel Boens, Noel Filarowski, Aleksander |
author_facet | Martyniak, Agata Lipkowski, Pawel Boens, Noel Filarowski, Aleksander |
author_sort | Martyniak, Agata |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-3249559 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Springer-Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-32495592012-01-11 Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium Martyniak, Agata Lipkowski, Pawel Boens, Noel Filarowski, Aleksander J Mol Model Original Paper 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. Springer-Verlag 2011-04-27 2012 /pmc/articles/PMC3249559/ /pubmed/21523531 http://dx.doi.org/10.1007/s00894-011-1075-7 Text en © The Author(s) 2011 https://creativecommons.org/licenses/by-nc/4.0/ This article is distributed under the terms of the Creative Commons Attribution Noncommercial License which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited. |
spellingShingle | Original Paper Martyniak, Agata Lipkowski, Pawel Boens, Noel Filarowski, Aleksander Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title | Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title_full | Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title_fullStr | Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title_full_unstemmed | Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title_short | Electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
title_sort | electron-topological, energetic and π-electron delocalization analysis of ketoenamine-enolimine tautomeric equilibrium |
topic | Original Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3249559/ https://www.ncbi.nlm.nih.gov/pubmed/21523531 http://dx.doi.org/10.1007/s00894-011-1075-7 |
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