Structural Analysis of Methyl-Substituted Nitrosobenzenes and Nitrosoanisoles

Eric Bosch, Missouri State University

Abstract

The structures of a series of simple nitrosoarenes: o-nitrosotoluene, nitrosomesitylene, nitrosoprehnitene, 2-methyl-4-nitrosoanisole and 2,6-dimethyl-4-nitrosoanisole are reported. The nitrosoarenes studied adopt one of two orientations in the solid state. In one group (nitrosophrenitene, 2,6-dimethyl-4-nitrosoanisole and 2-methyl-4-nitrosoanisole) the nitroso moiety is coplanar with the arene and the nitrosoarenes exist as monomers (ArNO) in the solid state. In contrast the nitroso group in o-nitrosotoluene and nitrosomesitylene is orthogonal to the arene and these nitrosoarenes exist as trans dimers ArN(O)N(O)Ar.