Tautomerism of peroxyacetic acid derivatives: a quantum chemical study View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2005-09

AUTHORS

D. Yu. Zubarev, N. B. Filimonova, E. N. Timokhina, K. V. Bozhenko, N. I. Moiseeva, S. P. Dolin, A. E. Gekhman, I. I. Moiseev

ABSTRACT

The electronic and molecular structures and the relative stabilities of organic peracids X=C(R)-COOH and their cyclic tautomers, dioxiranes , with R = Me, CF3; X = O, NH, were studied using the ab initio Hartree-Fock method and the density functional theory (B3LYP version) as well as at the MP2-MP4 Møller-Plesset levels of perturbation theory. Geometry optimization was performed by the UHF and B3LYP methods with the 6-31G** basis set and at the MP2/cc-pvtz level of theory. The acyclic form of the peracid is more stable than the cyclic dioxirane form irrespective of the nature of the substituent. The energy difference between these tautomers increases as the CF3 and NH groups are replaced by Me and O, respectively. Parameters of the activation barrier to tautomeric conversion increase in parallel with enhancement of the electron-accepting properties of both substituents. The transition state of tautomeric interconversion, which is topologically similar to the acyclic structure of the carbonyl oxide derivative R(HX)C=O+-O−, was found and characterized taking peroxyacetic acid as an example. The characteristic features of the transition state are an intramolecular “multicenter” H-bond and the charge distribution that is inconsistent with the canonical structure mentioned above. An appropriate reaction coordinate for the transformation of the quasi-tetrahedral dioxirane structure into a planar peroxyacetic acid structure is provided by the dihedral angle. Deprotonated anionic systems are characterized by much smaller differences between the relative stabilities of the open and closed forms of isomers and by much lower activation barriers to isomeric conversions. More... »

PAGES

2023-2033

References to SciGraph publications

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URI

http://scigraph.springernature.com/pub.10.1007/s11172-006-0074-9

DOI

http://dx.doi.org/10.1007/s11172-006-0074-9

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https://app.dimensions.ai/details/publication/pub.1037134240


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194 grid-institutes:grid.4886.2 schema:alternateName N. M. Emanuel’ Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation
195 schema:name N. M. Emanuel’ Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation
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197 grid-institutes:grid.77642.30 schema:alternateName People’s Friendship University of Russia, 6 ul. Miklukho-Maklaya, 117198, Moscow, Russian Federation, 6
198 schema:name People’s Friendship University of Russia, 6 ul. Miklukho-Maklaya, 117198, Moscow, Russian Federation, 6
199 rdf:type schema:Organization
 




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