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- Title
Reinvestigation into the ring-opening process of monochloroethylene oxide by quantum chemical calculations.
- Authors
Shinoda, Hiroyuki; Mori, Yoshihiro; Mizuguchi, Mineyuki
- 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
- Subjects
QUANTUM theory; DENSITY functionals; FUNCTIONAL analysis; CARBON; OXYGEN; ALDEHYDES; QUANTUM chemistry; PHYSICAL &; theoretical chemistry
- Publication
International Journal of Quantum Chemistry, 2006, Vol 106, Issue 4, p952
- ISSN
0020-7608
- Publication type
Article
- DOI
10.1002/qua.20843