Y. Ohkatsu et al., Consideration on the effect of ortho-substituents of phenols by semiempirical molecular orbital method MOPAC, POLYM DEGR, 67(3), 2000, pp. 541-545
A MOPAC calculation is performed to explain the new ortho-substitutent effe
ct of phenols proposed by the authors; an alpha-hydrogen of an ortho-substi
tuent being used to regenerate a phenol from the phenoxy radical. The benzy
l radical derived from the intramolecular hydrogen transfer of a phenoxy ra
dical is found to be as stable as, or more stable than, the phenoxy radical
. The regenerated phenol also is strikingly more stable than a quinoid type
compound formed by the reaction of a phenoxy radical with another peroxy r
adical. Thus, the new ortho-substituent effect mentioned above can also be
well explained by this work. (C) 2000 Elsevier Science Ltd. All rights rese
rved.