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Reinvestigation into the ring-opening process of monochloroethylene oxide by quantum chemical calculations

Authors

  • Hiroyuki Shinoda,

    Corresponding author
    1. Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0164, Japan
    • Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0164, Japan
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  • Yoshihiro Mori,

    1. Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0164, Japan
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  • Mineyuki Mizuguchi

    1. Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0164, Japan
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Abstract

Density functional theory (DFT) computation with B3LYP/6-31++G** has been performed for the ring-opening process of monochloroethylene oxide. In this study, the energy changes of an isolated monochloroethylene oxide, an O-protonated one and a Cl-protonated one, were investigated with respect to the stretching of the C[BOND]O bond length. The increased energy in an O-protonated system is fairly slow compared with that in a neutral system. In an O-protonated system, rupturing of the C[BOND]O bond, in which the carbon atom in the bond binds to the chlorine atom, occurs more easily than another C[BOND]O bond rupture. This fact is in agreement with ideas accepted in organic chemistry. Intrinsic reaction coordinate (IRC) calculations were performed for the O-protonated system, which gave the activation energy of the ring rupture as 3.89 kcal/mol. This also revealed that the production of an aldehyde occurred by a two-step reaction, that is, the first ring-opening process and following transfer of the chlorine atom. LMO wave functions were used to analyze the reaction mechanism. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2006

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