Radical hydroxylation of aromatic hydrocarbons examined by MINDO/3 methods View Full Text


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Article Info

DATE

1986-01

AUTHORS

V. V. Lobanov, N. A. Vysotskaya, E. A. Rabovskaya, V. I. Bogillo

ABSTRACT

MINDO/3 calculations have been made on the potential-energy surfaces for the attachment of OH. radicals to benzene (1) and naphthalene (2) in the vapor state. The activation energies of these reactions are calculated as 88 and 58 kJ/mole. while the enthalpies at 298K are calculated as −211 and −199 kJ/mol. The transition states in (1) and (2) lie closer to the reagents than the products on the reaction coordinate, while (1) has an earlier transition state than does (2). The transition states in these reactions have high dipole moments: 3.1 and 3.6 D, respectively, which are due to charge transfer from the hydrocarbons to the OH.. Quantum-chemical calculations and kinetic data on the reactions of aromatic hydrocarbons with OH. in aqueous solution indicate that the mechanism is probably not one involving electron transfer and a rate-limiting stage in the attachment. These processes are of high performance because the radicals are of high stability, while polar effects determine the selectivity. More... »

PAGES

17-22

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Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf00525299

DOI

http://dx.doi.org/10.1007/bf00525299

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1034585365


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