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

Skylaris, C-K; Igglessi-Markopoulou, O; Detsi, A; Markopoulos, J

dc.contributor.author	Skylaris, C-K	en
dc.contributor.author	Igglessi-Markopoulou, O	en
dc.contributor.author	Detsi, A	en
dc.contributor.author	Markopoulos, J	en
dc.date.accessioned	2014-03-01T01:18:49Z
dc.date.available	2014-03-01T01:18:49Z
dc.date.issued	2003	en
dc.identifier.issn	0301-0104	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/15217
dc.subject	Chemical Shift	en
dc.subject	Density Functional	en
dc.subject	Gibbs Free Energy	en
dc.subject	Nmr Spectroscopy	en
dc.subject	Nuclear Magnetic Resonance	en
dc.subject	Thermal Effects	en
dc.subject.classification	Chemistry, Physical	en
dc.subject.classification	Physics, Atomic, Molecular & Chemical	en
dc.subject.other	3 acetyltetramic acid	en
dc.subject.other	3 acetyltetronic acid	en
dc.subject.other	tetramic acid derivative	en
dc.subject.other	tetronic acid derivative	en
dc.subject.other	unclassified drug	en
dc.subject.other	ab initio calculation	en
dc.subject.other	article	en
dc.subject.other	carbon nuclear magnetic resonance	en
dc.subject.other	chemical structure	en
dc.subject.other	density	en
dc.subject.other	energy	en
dc.subject.other	mathematical analysis	en
dc.subject.other	nuclear magnetic resonance spectroscopy	en
dc.subject.other	proton nuclear magnetic resonance	en
dc.subject.other	quantitative analysis	en
dc.subject.other	structure analysis	en
dc.subject.other	temperature sensitivity	en
dc.title	Density functional and ab initio study of the tautomeric forms of 3-acetyl tetronic and 3-acetyl tetramic acids	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/S0301-0104(03)00359-8	en
heal.identifier.secondary	http://dx.doi.org/10.1016/S0301-0104(03)00359-8	en
heal.language	English	en
heal.publicationDate	2003	en
heal.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 DeltaG 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 H-1 and C-13 chemical shifts are in agreement with the experimental values from NMR spectroscopy. (C) 2003 Elsevier B.V. All rights reserved.	en
heal.publisher	ELSEVIER SCIENCE BV	en
heal.journalName	Chemical Physics	en
dc.identifier.doi	10.1016/S0301-0104(03)00359-8	en
dc.identifier.isi	ISI:000185239400004	en
dc.identifier.volume	293	en
dc.identifier.issue	3	en
dc.identifier.spage	355	en
dc.identifier.epage	363	en