The nature of hydrogen bonding in hydrotrioxides of methyl α-methylbenzyl ether and α-methylbenzyl alcohol. Are hydrotrioxides self-associated in solutions?

Abstract

¹ H and ¹³C N.m.r. spectroscopic evidence supports the hypothesis of the self-association of hydrotrioxides (2a) and (2b); inspection of molecular models of dimeric forms of these hydrotrioxides by taking into account the equilibrium geometry of methyl hydrotrioxide, calculated by the ab initio method at the STO 4-31G level, reveals two nearly optimal hydrogen bonding geometries in the associated hydrotrioxide species.