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The question of pentaphenylethyl: An AM1 study
Author(s) -
Smith William B.
Publication year - 1995
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.610080307
Subject(s) - chemistry , radical , dissociation (chemistry) , decomposition , computational chemistry , hydrocarbon , bond dissociation energy , photochemistry , organic chemistry
Semi‐empirical AM1 theoretical calculations were carried out on the pentaphenylethyl and 9‐trityfluorenyl free radicals, related radicals and their precursor hydrocarbons. Previous reports of the preparation of the former radical have been questioned, although the existence of the second is on secure ground. Based on simple energy considerations, it is concluded that pentaphenylethyl should be as readily prepared. However, the acidity of the precursor hydrocarbon is considerably less than that of 9‐tritylfluorene, and possible radical decomposition via dissociation to triphenylmethyl and diphenylcarbene is calculated to be more facile than the corresponding decomposition of 9‐tritylfluorenyl. A previous postulation of a rapid phenyl equilibration of the pentaphenylethyl radical is shown to be untenable.