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Density functional and ab initio study of the tautomeric forms of 3-acetyl tetronic and 3-acetyl tetramic acids

Density functional and ab initio study of the tautomeric forms of 3-acetyl tetronic and 3-acetyl tetramic acids
Density functional and ab initio study of the tautomeric forms of 3-acetyl tetronic and 3-acetyl tetramic acids
We propose all the accessible paths of interconversion between the tautomers of 3-acetyl tetronic and 3-acetyl tetramic acids by performing calculations with the density functional B3LYP method and the ab initio MP2 method. Our findings clarify at the atomic level the mechanisms of the equilibria between these tautomers, a topic so far only partially understood on the basis of studies by nuclear magnetic resonance (NMR) spectroscopy. We show that thermal effects via relative Gibbs free energies ?G must be taken into account in order to reach good quantitative agreement with the available experimental information on the ratios of the most stable tautomers. The calculated 1H and 13C chemical shifts are in agreement with the experimental values from NMR spectroscopy.
355-363
Skylaris, C.-K.
8f593d13-3ace-4558-ba08-04e48211af61
Igglessi-Markopoulou, O.
5ce1a6d8-8446-4797-9416-5c5a550b2ca8
Detsi, A.
3c021521-4b69-445c-b575-94aca38a85a2
Markopoulos, J.
0795d115-70c9-4f93-9779-fc2fb0bcbf68
Skylaris, C.-K.
8f593d13-3ace-4558-ba08-04e48211af61
Igglessi-Markopoulou, O.
5ce1a6d8-8446-4797-9416-5c5a550b2ca8
Detsi, A.
3c021521-4b69-445c-b575-94aca38a85a2
Markopoulos, J.
0795d115-70c9-4f93-9779-fc2fb0bcbf68

Skylaris, C.-K., Igglessi-Markopoulou, O., Detsi, A. and Markopoulos, J. (2003) Density functional and ab initio study of the tautomeric forms of 3-acetyl tetronic and 3-acetyl tetramic acids. Chemical Physics, 293 (3), 355-363. (doi:10.1016/S0301-0104(03)00359-8).

Record type: Article

Abstract

We propose all the accessible paths of interconversion between the tautomers of 3-acetyl tetronic and 3-acetyl tetramic acids by performing calculations with the density functional B3LYP method and the ab initio MP2 method. Our findings clarify at the atomic level the mechanisms of the equilibria between these tautomers, a topic so far only partially understood on the basis of studies by nuclear magnetic resonance (NMR) spectroscopy. We show that thermal effects via relative Gibbs free energies ?G must be taken into account in order to reach good quantitative agreement with the available experimental information on the ratios of the most stable tautomers. The calculated 1H and 13C chemical shifts are in agreement with the experimental values from NMR spectroscopy.

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More information

Submitted date: 15 April 2003
Published date: 30 July 2003

Identifiers

Local EPrints ID: 39009
URI: http://eprints.soton.ac.uk/id/eprint/39009
PURE UUID: 39e8cea9-c6d8-427f-9088-76edd7725748
ORCID for C.-K. Skylaris: ORCID iD orcid.org/0000-0003-0258-3433

Catalogue record

Date deposited: 16 Jun 2006
Last modified: 16 Mar 2024 03:51

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Contributors

Author: C.-K. Skylaris ORCID iD
Author: O. Igglessi-Markopoulou
Author: A. Detsi
Author: J. Markopoulos

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