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Kinetics and mechanism of the pyridinolysis of benzenesulfonyl chlorides in methanol

✍ Scribed by Sung Wan Hong; Han Joong Koh; Ikchoon Lee

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
65 KB
Volume
12
Category
Article
ISSN
0894-3230

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✦ Synopsis

The kinetics of reactions between Y-benzenesulfonyl chlorides and X-pyridines in methanol at 35.0 Β°C were investigated. Strong para p-acceptors, X = p-CN and p-COCH 3 , give good linear fits to BrΓΈnsted-type plots with low b X (=0.32-0.45) but show positive deviations from linear Hammett plots (& X = Γ€1.98 to Γ€2.79). Excellent linear Hammett plots are obtained with substituent variations in the substrate with & Y = 0.6-1.0 which are similar to those for the anilinolysis. These results support an S N 2 mechanism for the pyridinolysis of benzenesulfonyl chlorides. The cross-interaction constant r XY is a small negative value (Γ€0.48). Much smaller magnitudes of b X , r X and r XY than the corresponding values for the anilinolysis suggest that the transition state is formed at a relatively earlier position along the reaction coordinate than for anilinolysis.

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