Isolation and low-temperature x-ray analysis of intramolecular triarylmethane-triarylmethylium complex: preference for a C-H-bridged unsymmetric structure exhibiting a facile 1,5-hydride shift and charge-transfer interaction

Hidetoshi Kawai; Takashi Takeda; Kenshu Fujiwara; Takanori Suzuki

doi:10.1021/ja053161h

Isolation and low-temperature x-ray analysis of intramolecular triarylmethane-triarylmethylium complex: preference for a C-H-bridged unsymmetric structure exhibiting a facile 1,5-hydride shift and charge-transfer interaction

J Am Chem Soc. 2005 Sep 7;127(35):12172-3. doi: 10.1021/ja053161h.

Authors

Hidetoshi Kawai¹, Takashi Takeda, Kenshu Fujiwara, Takanori Suzuki

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

PMID: 16131165
DOI: 10.1021/ja053161h

Abstract

The intramolecular triarylmethane-methylium complex with an averaged C2v-symmetry was successfully generated by N-methylation of the acridine-acridan hybrid. Theoretical calculation and VT-NMR analyses in solution indicate the unsymmetric geometry for the three-center bond, which was finally confirmed crystallographically. Significant degree of CT interaction is induced through the very short C-H...C+ contact.