Structure and conformation of 1,4-dihydrobenzene, l,4-dihydroanaphthalene, and 9,10-dihydroanthracene. A theoretical study

Journal Article · Thu Mar 11 23:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00345a021· OSTI ID:5658570

Lipkowitz, K B ^[1]; Rabideau, P W; Raber, D J; Hardee, L E; Schleyer, P V.R.; Kos, A J; Kahn, R A

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1. Univ. of Indianapolis, IN

The title compounds have been studied by using both molecular mechanics (MMI and MM2) and molecular orbital (MINDO/3, MNDO, and ab initio (3-21G basis)) calculations. The optimum structure is found to be planar in each case, although the energy required for nonplanar distortion is small and decreases regularly with the degree of benzannulation. The large puckering amplitudes to be expected explain the experimentally observed behavior. 4 figures, 1 table.

• OSTI ID: 5658570
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:6; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ANTHRACENE
AROMATICS
BENZENE
CONDENSED AROMATICS
CONFORMATIONAL CHANGES
HYDROCARBONS
MECHANICS
MOLECULAR ORBITAL METHOD
MOLECULAR STRUCTURE
NAPHTHALENE
ORGANIC COMPOUNDS