Ryotaro Tsuji, K. Komatsu, K. Takeuchi
Aug 1, 1993
Citations
0
Influential Citations
17
Citations
Journal
Journal of Physical Organic Chemistry
Abstract
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.