DISPLACEMENT REACTIONS .19. RATES AND HEATS OF REACTION OF NUCLEOPHILES WITH BETA-PROPIOLACTONE

被引:11
作者
DAVIS, RE
SUBA, L
KLIMISHI.P
CARTER, J
机构
[1] Department of Chemistry, Purdue University, Lafayette
关键词
D O I
10.1021/ja01029a022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The nucleophilic constants of a thiol, mercaptoethylammonium ion, have been determined using β-propiolactone as a substrate in aqueous solution at 25°. The data are correlated with the nucleophilic properties of HO-, H2O, HS- H2S, RS-, and RSH. The trends are regular and good predictions can be made. The reaction of hydroxide ion with β-propiolactone is discussed. The fraction of attack at the methylene carbon has been predicted but not yet tested. The rates and heats of reaction of β-propiolactone with NO2-, SO32-, -SCN, -OH, CH3COO-, and S3O32- have been measured. The ΔH values are reported and discussed. © 1969, American Chemical Society. All rights reserved.
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页码:104 / &
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