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Perchlorate Esters. Part 3. Correlation of the Rates of Reaction of Arenesulphonate Ions with Methyl Perchlorate in Acetonitrile

DOI: 10.1039/P29810000049

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 49 - 52 (1981)

Update date:2022-08-30

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Authors:

Kevill, Dennis N.Kevill, Dennis N.

Lin, Gloria Meichia L.Lin, Gloria Meichia L.

Bahari, Mohd S.Bahari, Mohd S.

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Article abstract of DOI:10.1039/P29810000049

Second-order rate coefficients for the reactions of acetonitrile solutions of tetra-n-butylammonium benzensulphonate and seven meta- and para-substituted derivatives with methyl perchlorate, at 0.3 deg C lead to a Hammet ρ value (-1.10 +/- 0.04) essentially identical to those previously reported for reactions with other powerful methylating agents.When silver ion is substituted for tetra-n-butylammonium ion, the second-oreder rate coefficients become concetration dependent and the fall of with increasing salt concetration can be rationalised on the basis of only free anions being reactive.The calculated degrees of dissociation are applied tothe previously studied silver0ion assisted reaction of silver toluene-p-sulphonate with methyl iodide.

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