A computational study of the of a boron-oxygen-carbon formation linkage. - The reaction of monohydroxy borane with methanol

Boronic acids are well known to form covalent linkages with compounds containing 1,2- or 1,3-diol moieties to form cyclic boronic esters. This unique ability of the boronic acid functional group has led to its use as the recognition entity in carbohydrate sensors. In the present computational study we discuss the formation of a prototypical boron-oxygen-carbon linkage by investigating the dehydration reaction: monohydroxy borane + methanol --> borane methyl ether + water; density functional theory at the B3LYP/6-311++G** computational level is employed. Several alternative mechanisms for this reaction are considered and the influence of aprotic solvents and base catalysts are also discussed. (C) 2003 Elsevier B.V. All rights reserved.