Bond dissociation energy of the phenol O{single bond}H bond from ab initio calculations

Document Type

Article

Publication Date

6-12-2006

Abstract

The phenol O{single bond}H bond dissociation energy (BDE) is currently disputed, despite its importance in combustion chemistry and in the reactions of antioxidants such as vitamin E. We have studied this BDE using the computational methods G3, G3B3 and CBS-APNO, with bond-isodesmic work reactions. These calculations yield a BDE of 89.0 ± 1.0 kcal mol-1, which supports other recent calculations [B.J. Costa Cabral, S. Canuto, Chem. Phys. Lett. 406 (2005) 300]. From our BDE we determine the enthalpy of formation of the phenoxy radical to be 13.9 ± 1.0 kcal mol-1. Comparison of the phenol C{single bond}H BDE with the vinyl alcohol H{single bond}CH{double bond, long}CHOH BDE reveals the bond in phenol to be around 3 kcal mol-1 stronger than that in vinyl alcohol. Replacement of a H atom with the OH group on benzene or ethylene strengthens the C{single bond}H bonds on adjacent carbons by 3 to 4 kcal mol-1. © 2006 Elsevier B.V. All rights reserved.

Identifier

33646833610 (Scopus)

Publication Title

Chemical Physics Letters

External Full Text Location

https://doi.org/10.1016/j.cplett.2006.04.022

ISSN

00092614

First Page

42

Last Page

45

Issue

1-3

Volume

424

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