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Title: Conformational Analysis of (±)-(1,1′-Biindene)-3,3′ -dione, 2,2′,3,3′-Tetrahydro-(1,1′-binaphthalene)-4,4′ (1H,1′H)-dione, and (1,1′-Bibenzosuberene)-5,5′-dione
Authors: Lam, Y. 
Ma, N.L.
Huang, H.-H. 
Liang, E.
Issue Date: 2003
Citation: Lam, Y., Ma, N.L., Huang, H.-H., Liang, E. (2003). Conformational Analysis of (±)-(1,1′-Biindene)-3,3′ -dione, 2,2′,3,3′-Tetrahydro-(1,1′-binaphthalene)-4,4′ (1H,1′H)-dione, and (1,1′-Bibenzosuberene)-5,5′-dione. Bulletin of the Chemical Society of Japan 76 (10) : 1897-1902. ScholarBank@NUS Repository.
Abstract: The dipole moments of (±)-(1,1′-biindene)-3,3′-dione 1, (±)-2,2′,3,3′-tetrahydro-(1,1′-binaphthalene)-4, 4′(1H,1′H)-dione 2, and (±)-(1,1′ -bibenzosuberene)-5,5′-dione 3 in carbon tetrachloride and benzene were measured over a range of temperatures. Analyses of the relative permittivity data in carbon tetrachloride and benzene showed that at 25 °C, 1 exists predominantly in the gauche conformation, whilst 2 and 3 favor the trans form. The experimentally derived values of the energy difference between the gauche and trans rotamers and the gauche/trans population quotient were compared with values predicted by molecular-orbital calculations. The crystal and molecular structures of 2 and 3 were determined by single-crystal X-ray diffraction methods. Both compounds exist in the trans conformation in the solid-state. Dynamic 1H NMR was employed to 3 in order to determine the activation parameters for the barriers to rotation in solution.
Source Title: Bulletin of the Chemical Society of Japan
ISSN: 00092673
DOI: 10.1246/bcsj.76.1897
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