Structure and conformation of dihydroaromatic compounds. 1-alkyl-1,4-dihydrobenzenes, 1-alkyl-1,4-dihydronaphthalenes, and 9-alkyl-9,10-dihydroanthracenes
The molecular geometries of 1-alkyl-1,4-dihydrobenzenes, 1-alkyl-1,4-dihydronaphthalenes, and 9-alkyl-9,10-dihydroanthracenes have been evaluated by empirical force-field calculations. Unlike the parent dihydroaromatics, the alkyl-substituted hydrocarbons all exhibit optimum geometries that are nonplanar, and the distortion from planarity increases with the steric bulk of the substituent. In contrast to earlier suggestions of a boat-to-boat equilibrium, all of the 1,4-dihydrobenzenes studied have a single energy minimum in which the substituent occupies a pseudoaxial position. Several of the dihydronaphthalene and dihydroanthracene derivatives exhibit two distinct nonpolar energy minima, but the pseudoaxial conformation is much more stable than the pseudoequatorial form in each case. Consequently, even these compounds can be considered to exist in a single conformation.
- Research Organization:
- Univ. of South Florida, Tampa
- DOE Contract Number:
- AC02-79ER10339
- OSTI ID:
- 6301541
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 104; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ANTHRACENE
AROMATICS
BENZENE
CONDENSED AROMATICS
DATA
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
MOLECULAR STRUCTURE
NAPHTHALENE
NUMERICAL DATA
ORGANIC COMPOUNDS