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The gas‐phase reactivity of epichlorohydrin with hydroxide
Author(s) -
Merrill G. N.
Publication year - 2004
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.722
Subject(s) - chemistry , epichlorohydrin , methylene , reactivity (psychology) , nucleophile , ring (chemistry) , hydroxide , alkyl , medicinal chemistry , ab initio , gas phase , substrate (aquarium) , phase (matter) , carbon atom , computational chemistry , organic chemistry , catalysis , medicine , oceanography , alternative medicine , pathology , geology
The reaction of hydroxide with epichlorohydrin in the gas phase was investigated with ab initio calculations. Three mechanisms were examined, each corresponding to nucleophilic attack at a different carbon atom of the substrate. It was determined that through attack at the ring methylene position was favored, whereas attacks at the alkyl methylene or ring methine positions were found to have larger activation energies. These results are consistent with experimental results found in the literature. Copyright © 2004 John Wiley & Sons, Ltd.