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Structural study on 1‐phenyl‐ and 1‐(2‐naphthyl)‐8‐tropylionaphthalene hexafluoroantimonates
Author(s) -
Tsuji Ryotaro,
Komatsu Koichi,
Takeuchi Ken'ichi,
Shiro Motoo,
Cohen Shmuel,
Rabinovitz Mordecal
Publication year - 1993
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610060802
Subject(s) - chemistry , computational chemistry , stereochemistry
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.