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KMID : 1059519890330050468
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Journal of the Korean Chemical Society
1989 Volume.33 No. 5 p.468 ~ p.476
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Kinetics of Methanolysis of Arenesulfonyl Chloride in the Presence of Pyridine
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Kim Hyong-Tae
Lee Ik-Choon
Rim Myung-Soo
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Abstract
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Kineties for the reactions of pyridines with 1-anthracenesulfonyl chloride (1-ASC) and 3-phenanthrenesulfonyl chloride (3-PSC) was investigated in methanol as solvent. Structural variation in pyridine followed Brφ nsted and Hammett relations for both 1-ASC and 3-PSC; the corresponding coefficients,β and ρ at 20℃ were 0.55, -3.5 for 1-ASC, and 0.43, -2.6 for 3-PSC respectively. Reactivity-selectivity principle was checked in competition system 1-ASC/3-PSC. As a result, this principle was found to hold at experimental temperatures, whereas to break down over in the range of isoselective temperature (34.3℃). Judging from the above results and activation parameters, we concluded that these reactions proceeded by synchronous SN2 mechanism in rate-determining step.
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