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A spin‐coupled investigation of the electrophilic addition of hydrochloric acid to ethylene
Author(s) -
Thorsteinsson T.,
Famulari A.,
Raimondi M.
Publication year - 1999
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1999)74:2<231::aid-qua18>3.0.co;2-y
Subject(s) - electrophile , chemistry , hydrochloric acid , ethylene , computational chemistry , electrophilic addition , density functional theory , spin states , inorganic chemistry , organic chemistry , catalysis
The gas‐phase reaction of hydrochloric acid and ethylene to give chloroethane is investigated in the framework of spin‐coupled (SC) theory, with emphasis on the widely accepted bimolecular mechanism. The transition‐state structure and intrinsic reaction coordinate path are studied in detail. Our results indicate that the driving force in the reaction is the electrophilic attack of the hydrogen atom in HCl on one of the ethylenic carbons. There is little evidence supporting the occurrence of a four‐membered transition state; rather, the spin‐coupled results suggest that the breaking of the HCl bond occurs before the CCl bond formation. These findings are supported by the results from a topological analysis of the total electron density. ©1999 John Wiley & Sons, Inc. Int J Quant Chem 74: 231–239, 1999