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Substituent effects on S N 2 reaction between substituted benzyl chloride and chloride ion in gas phase
Author(s) -
Ebrahimi A.,
HabibiKhorassani S. M.,
Doosti M.
Publication year - 2011
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/qua.22474
Subject(s) - chemistry , substituent , ion , ab initio , chloride , computational chemistry , nucleophilic substitution , molecule , molecular geometry , benzyl chloride , medicinal chemistry , organic chemistry , catalysis
Nucleophilic substitution reaction between some substituted benzyl chlorides and chloride ion has been investigated by ab initio and DFT methods. New calculated energy data are in better agreement with experimental data. The electron‐withdrawing groups increase the energy barriers and the electron‐donating groups decrease them. The changes of geometrical parameters and energy data are in good agreement with the results of atoms in molecules and natural bond orbital analyses. The relationship between Hammett coefficients and energy data (and geometry parameters) has been established and the ρ constant has been calculated for this reaction. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011