Journal
SCIENCE
Volume 295, Issue 5563, Pages 2245-2247Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1068849
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Rates of S(N)2 reactions of chloride ion with methyl- and tert-butyl-substituted chloroacetonitrile were measured by using Fourier transform-ion cyclotron resonance spectrometry to follow the isotopic exchange reaction. Barrier heights for these reactions indicate that steric effects in the gas phase are diminished relative to apparent steric effects in solution. We attribute the increased barrier in solution to a solvation effect. Monte Carlo simulations done using statistical perturbation theory confirm that steric hindrance to solvation contributes to S(N)2 barriers in solution.
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