Please use this identifier to cite or link to this item: https://doi.org/10.1039/b103740b
Title: Conformational analysis of meso- and (±)-2,3-dicyano-2,3-dicyclopropylbutane and 1,2-dicyanotetracyclopropylethane
Authors: Lam, Y.-L. 
Ming Wah Wong 
Huang, H.-H. 
Liang, E.
Issue Date: 2001
Source: Lam, Y.-L., Ming Wah Wong, Huang, H.-H., Liang, E. (2001). Conformational analysis of meso- and (±)-2,3-dicyano-2,3-dicyclopropylbutane and 1,2-dicyanotetracyclopropylethane. New Journal of Chemistry 25 (10) : 1325-1329. ScholarBank@NUS Repository. https://doi.org/10.1039/b103740b
Abstract: The dipole moments of meso-2,3-dicyano-2,3-dicyclopropylbutane meso-1, (±)-2,3-dicyano-2,3-dicyclopropylbutane (±)-1 and 1,2-dicyanotetracyclopropylethane 2 in carbon tetrachloride and benzene have been measured over a range of temperatures. Analyses of the relative permittivity data show that at 25°C, meso-1 and (±)-1 favour the trans form. However, replacement of the methyl groups in 1 with cyclopropyl moieties completely reverses the trans ⇄ gauche equilibrium, such that 2 exists in 74% gauche conformation. The experimentally derived values of the energy difference between the gauche and trans conformers and the gauche/trans population quotients were compared with values predicted by molecular orbital calculations. Theory predicts that the conformational preference of the substituted dicyanoethanes is strongly influenced by solvent polarity. The crystal and molecular structures of meso-1 and 2 were determined by single-crystal X-ray diffraction methods. Both compounds exist in the trans conformation in the solid state.
Source Title: New Journal of Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/93356
ISSN: 11440546
DOI: 10.1039/b103740b
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