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Rate and product studies in the solvolyses of N,N-dimethylsulfamoyl and 2-propanesulfonyl chlorides

Title
Rate and product studies in the solvolyses of N,N-dimethylsulfamoyl and 2-propanesulfonyl chlorides
Author
경진범
Issue Date
2006-02
Publisher
ROYAL SOC CHEMISTRY
Citation
ORGANIC & BIOMOLECULAR CHEMISTRY, v. 4, No. 8, Page. 1580-1586
Abstract
Contrary to earlier suggestions of an S(N)1 pathway for solvolyses of N,N-dimethylsulfamoyl chloride (1), an extended Grunwald-Winstein equation treatment of the specific rates of solvolysis in 32 solvents shows an appreciable sensitivity towards changes in both solvent nucleophilicity and solvent ionizing power. The actual values are very similar to those obtained in earlier studies of the solvolyses of sulfonyl and phosphoryl chlorides, solvolyses which are believed to proceed by an S(N)2 pathway. The observation of similar selectivities in aqueous-alcohol solvents further supports this assignment. In a recent report, an addition-elimination (association-dissociation) pathway was proposed for solvolyses of 2-propanesulfonyl chloride (2). A severe multicollinearity problem has been removed by the addition of several specific rates of solvolysis in fluoroalcohol-containing solvents. The new analyses using the extended Grunwald-Winstein equation lead to sensitivities similar to those for 1 and the previously studied related compounds, and these solvolyses are also best described as following an S(N)2 pathway.
URI
https://pubs.rsc.org/en/content/articlehtml/2006/ob/b518129ahttp://repository.hanyang.ac.kr/handle/20.500.11754/107674
ISSN
1477-0520
DOI
10.1039/b518129a
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ETC > 연구정보
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