STRUCTURAL STUDY ON 1-PHENYL- AND 1-(2-NAPHTHYL)-8-TROPYLIONAPHTHALENE HEXAFLUOROANTIMONATES

Article abstract of DOI:10.1002/poc.610060802

The molecular structures of 1-phenyl- (5) and 1-(2-naphthyl)-8-tropylionaphthalene (6) hexafluoroantimonates were determined by x-ray crystallography and compared with those of 1,8-diphenylnaphthalene and related compounds.In these compounds, the two aromatic substituents face each other in a nearly parallel conformation with a splayed-out arrangement.In the cations 5 and 6, the distance between the facing rings is appreciably shorter than that of other 1,8-diarylnaphthalenes, suggesting the presence of some attractive force.This attraction is ascribed to an intramolecular charge-transfer interaction, and seems to bring about a slight inward bending of the 2-naphthyl substituent in the cation 6.AM1 calculations were carried out for these cations and the results are discussed in comparison with the results of x-ray crystallography.