Nitrenium ions. Part 4.1 Reactivity and crystal structure of 1-methyl-2-phenyl-3-N-benzoyloxyindole iminium perchlorate and reactivity of N,N-dimethylamino-p-N-benzoyloxyaniline nitrenium chloride with 2-phenylindole

Abstract

1-Methyl-2-phenyl-3-nitrosoindole and N,N-dimethyl-p-nitrosoaniline react with benzoyl chloride to form salts behaving like iminium and nitrenium ions respectively. The structure of the ion formed in the case of the nitrosoindole was elucidated by X-ray analysis. The charge density distribution of both ions was calculated on the basis of the structure parameters and by AM1 calculations and their reactivity was interpreted on the basis of structural parameters and the calculated distribution of their positive charge.