Quantum chemical insights into regioselective hydrolysis of C60F36

Abstract

The hydrolysis reaction of fluorinated C₆₀ to prepare fullerenols has been exposed by density functional theory for the first time. C₆₀F₃₆ was proved to hydrolyze via an S_N2′ mechanism rather than S_N1 or S_N2 mechanism, and it is revealed that the hydrolysis is a regioselective reaction which may stem from the charge population of C₆₀F₃₆. The two adjacent carbon atoms connected by an isolated double bond possess opposite reactivities, and these two atoms exhibit a strong competition with each other to be attacked by water molecules during the hydrolysis. Bond order analyses using Wiberg indexes indicate that such a hydrolysis should be a concerted yet asynchronous reaction. Hydrolysis of fluorinated C₆₀ can be considered as a method for fullerenol production via which structure-defined fullerenol will be obtained, and this method is greatly superior to traditional methods.