A computational study into the reactivity of epichlorohydrin and epibromohydrin under acidic conditions in the gas phase and aqueous solution |
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| Authors: | E S Shields G N Merrill |
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| Institution: | 1. Department of Chemistry, University of Texas at San Antonio, Texas 78249‐0698, USA;2. Department of Chemistry, University of Texas at San Antonio, Texas 78249‐0698, USAOne UTSA Circle, Department of Chemistry, University of Texas at San Antonio, San Antonio, TX 78249‐0698, USA.=== |
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| Abstract: | Ab initio molecular orbital calculations have been carried out upon epichlorohydrin and epibromohydrin at the Hartree–Fock (HF) and Møller–Plesset (MP2) levels of theory to explore the reactivity of these species with respect to nucleophilic attack by water under acidic conditions in the gas phase and aqueous solution. These results suggest that nucleophilic attack occurs preferentially at the epoxy carbon atoms in both the gas phase and aqueous solution. These results are in contrast to those found for nucleophilic attack under basic conditions, where attack at the halocarbon atom is competitive with that at the epoxy carbon atoms. Copyright © 2007 John Wiley & Sons, Ltd. |
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| Keywords: | epibromohydrin epichlorohydrin water reaction mechanism gas phase solution ab initio modeling |
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