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The leaving group dependence in the rates of solvolysis of 1,2‐diphenylethyl system
Author(s) -
Santhosh Kumar D.,
Jayakumar K. P.,
Balachandran S.
Publication year - 2010
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.1662
Subject(s) - solvolysis , chemistry , carbocation , steric effects , chloride , aqueous solution , leaving group , medicinal chemistry , organic chemistry , halocarbon , catalysis , hydrolysis
1,2‐Diphenylethyl chloride undergoes solvolysis by S N 1 mechanism in aqueous organic solvents. The α ‐phenyl group of 1,2‐diphenylethyl chloride enters into conjugation with the developing carbocationic centre. The β ‐phenyl group on the other hand was unable to extend its conjugation via neighbouring group participation due to steric inhibition of resonance in the formation of non‐classical carbocation. 1,2‐Diphenylethyl chloride thus behaves similar to 1‐phenylethyl chloride in its solvolysis pattern. The solvolytic rate studies of chloride and methanesulphonate of 1,2‐diphenylethyl alcohol in various aqueous organic solvents show that the dispersion observed in the Winstein–Grunwald plot is not due to a change in leaving group but due to the difference in solvation requirements of aromatic and aliphatic groups. Copyright © 2010 John Wiley & Sons, Ltd.