Twisted Polycyclic Aromatic Hydrocarbons. Structural Studies of Protic and Deuteriated 1,2,3,4-Tetraphenyltriphenylenes

Robert A. Pascal, Donna Van Engen, Bart Kahr, William D. McMillan

Research output: Contribution to journalArticlepeer-review

Abstract

An X-ray crystallographic study of 1,2,3,4-tetraphenyltriphenylene shows that the polycyclic nucleus of this molecule is substantially twisted due to severe nonbonded interactions between the triphenylene hydrogen atoms and the proximal carbons of the 1- and 4-phenyl groups. The two independent molecules in the crystallographic unit cell exhibit twists of 28.1° and 30.9°, slightly less than the 33° twist predicted by MM2(85). 1,2,3,4-Tetraphenyl[5,6,7,8,9,10,ll,12-2H8]triphenylene was prepared to determine if the twist angle would be altered by deuterium substitution, and it was found that the X-ray structuresof the deuteriated and protic molecules did not differ significantly.

Original languageEnglish (US)
Pages (from-to)1687-1689
Number of pages3
JournalJournal of Organic Chemistry
Volume53
Issue number8
DOIs
StatePublished - Apr 1 1988

ASJC Scopus subject areas

  • Organic Chemistry

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