Substitution at saturated carbon. Part XVIII. The effect of alcoholic solvents on rate constants for S N and S E reactions
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 623-628
- https://doi.org/10.1039/p29750000623
Abstract
Rate constants are reported for reactions between the following nine pairs of reactants, using a number of pure alcohols as solvents: Et3N and Etl,Prn 3N and Mel, Me4Sn and HgCl2, Me4Sn and Hgl2, Et4Sn and HgCl2, Et4Sn and Hgl2, Et4Sn and Hg(OAc)2, Me4Sn and I2, and Et4Sn and I2. Comparisons have been carried out between the effect of alcoholic solvents on ΔG‡ values for 21 SN and SE reactions, and it is shown that no simple solvent parameter can adequately correlate such solvent effects on the various reactions. However, in general, the retarding effect of the less polar alcohols on the organometallic substitutions lies between the very large solvent effect on the SN1 reaction of t-butyl halides and the much smaller solvent effect on the SN2 Menschutkin reactions. The reaction between Et3N and Etl and that between Prn 3N and Mel are anomalous in that molar rate constants in t-butyl alcohol are as high as rate constants in the much more polar solvent methanol.Keywords
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