¹H D.N.M.R. and X-Ray Structure of 2,2-Dimethyl-1-(Para-nitrophenyl)propyl Mesityl Sulfone

Abstract

2,2-Dimethyl-1-(p- nitrophenyl ) propyl mesityl sulfone (3), formed by an S_RN1 reaction between sodium mesitylenesulfinate and p-(1-chloro-2,2- dimethylpropyl )nitrobenzene displays a number of conformational interconversions in solution. The activation parameters for the rotation of the mesityl ring about the aryl-sulfur bond and the rotation of the p- nitrophenyl ring about the aryl-carbon bond were determined by ¹H d.n.m.r .spectroscopy. The conformation of (3) in the solid state, determined by X-ray crystallography, is very similar to the preferred ground-state conformation of the molecule in solution.