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A computational study into the reactivity of epichlorohydrin and epibromohydrin under acidic conditions in the gas phase and aqueous solution
Author(s) -
Shields E. S.,
Merrill G. N.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1255
Subject(s) - chemistry , epichlorohydrin , nucleophile , reactivity (psychology) , aqueous solution , ab initio , gas phase , computational chemistry , inorganic chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.