Journal of Computational Chemistry, volume 43, issue 15, pages 1000-1010
Keto-enol tautomerism from the electron delocalization perspective
Publication type: Journal Article
Publication date: 2022-04-12
Journal:
Journal of Computational Chemistry
Quartile SCImago
Q1
Quartile WOS
Q3
Impact factor: 3
ISSN: 01928651, 1096987X
General Chemistry
Computational Mathematics
Abstract
The equilibrium between keto and enol forms in acetylacetone and its derivatives is studied using electron delocalization indices and delocalization tensor density. We demonstrate how electron delocalization governs the equilibrium between keto and enol forms. The less stable enols have more distinct double and single bond character in the CCC fragment, while electron delocalization in this fragment is more pronounced in more stable enols. Looking for the origin of such behavior, we considered the one‐electron potentials entering the Euler equation for the electron density. We found that electron delocalization is mainly governed by the static exchange potential, which depends on the three‐dimensional atomic structure. It, however, does not distinguish differences in electron delocalization in more and less stable enols, the effect arising from the kinetic exchange contribution, which reflects spin‐dependent effects in the electron motion. The local depletion of kinetic exchange in the conjugated fragment yields the enhanced electron delocalization along the CCC bonds in more stable enols. Thus, a combination of considered descriptors allowed us to reveal the influence of electron delocalization on the equilibrium between keto and enol forms and showed the significant features of this phenomenon.
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Levina E. S. et al. Keto-enol tautomerism from the electron delocalization perspective // Journal of Computational Chemistry. 2022. Vol. 43. No. 15. pp. 1000-1010.
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Levina E. S., Khrenova M. G., Astakhov A. A., Tsirel’son V. S. Keto-enol tautomerism from the electron delocalization perspective // Journal of Computational Chemistry. 2022. Vol. 43. No. 15. pp. 1000-1010.
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TY - JOUR
DO - 10.1002/jcc.26858
UR - https://doi.org/10.1002%2Fjcc.26858
TI - Keto-enol tautomerism from the electron delocalization perspective
T2 - Journal of Computational Chemistry
AU - Astakhov, Andrey A
AU - Levina, Elena S.
AU - Khrenova, Maria G.
AU - Tsirel’son, V. S.
PY - 2022
DA - 2022/04/12 00:00:00
PB - Wiley
SP - 1000-1010
IS - 15
VL - 43
SN - 0192-8651
SN - 1096-987X
ER -
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@article{2022_Levina,
author = {Andrey A Astakhov and Elena S. Levina and Maria G. Khrenova and V. S. Tsirel’son},
title = {Keto-enol tautomerism from the electron delocalization perspective},
journal = {Journal of Computational Chemistry},
year = {2022},
volume = {43},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002%2Fjcc.26858},
number = {15},
pages = {1000--1010},
doi = {10.1002/jcc.26858}
}
Cite this
MLA
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Levina, Elena S., et al. “Keto-enol tautomerism from the electron delocalization perspective.” Journal of Computational Chemistry, vol. 43, no. 15, Apr. 2022, pp. 1000-1010. https://doi.org/10.1002%2Fjcc.26858.