Effect of ortho-SR groups on OH bond strength and H-atom donating ability of phenols: a possible role for the tyr-cys link in galactose oxidase active site?

…, S Menichetti, GF Pedulli, C Viglianisi

Index: Amorati, Riccardo; Catarzi, Francesca; Menichetti, Stefano; Pedulli, Gian Franco; Viglianisi, Caterina Journal of the American Chemical Society, 2008 , vol. 130, # 1 p. 237 - 244

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Citation Number: 37

Abstract

Rotation about the Ar-S bond in ortho-(alkylthio) phenols strongly affects the bond dissociation enthalpy (BDE) and the reactivity of the OH group. Newly synthesized sulfur containing heterocycles 3 and 4, where the-SR group is almost coplanar with the phenolic ring, are characterized by unusually low BDE (OH) values (79.6 and 79.2 kcal/mol, respectively) and by much higher reactivities toward peroxyl radicals than the ortho- ...