Acid-Catalyzed Hydrolysis of Some N,N-Dibenzylalkanesulfinamides in 50% Acetonitrile-Water

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The hydrolysis of some N,N-dibenzylalkanesulfinamides (RSONH(CH2Ph)(2); 1, R=Me; 2, R=Pr-i; 3, R=Bu-t; 4, R=1-adamantyl) has been studied in 50% (v:v) acetonitrile-water solutions of hydrobromic and hydrochloric acids, mainly at 44.8 degrees C, using ultraviolet (UV) spectrophotometry to determine pseudo first-order rate constants. The compounds were found to hydrolyze by concurrent bimolecular neutral, acid-catalyzed, and acid-dependent nucleophilic (halide ion) catalysis pathways. The last-named is predominant in reactions in HBr solutions, but in HCl solutions, the acid-catalyzed pathway is predominant. The results indicate that both steric and electronic effects are important in these reactions. There appears to be no mechanistic switchover in the series 14.
Publisher
TAYLOR & FRANCIS LTD
Issue Date
2013-06
Language
English
Article Type
Article
Keywords

CRYSTAL-STRUCTURES; NUCLEOPHILIC-SUBSTITUTION; SULFINAMIDES; NITROGEN; DERIVATIVES; PROTONATION; MECHANISMS; SULFUR; OXYGEN

Citation

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, v.188, no.6, pp.691 - 700

ISSN
1042-6507
DOI
10.1080/10426507.2012.704105
URI
http://hdl.handle.net/10203/175049
Appears in Collection
CH-Journal Papers(저널논문)
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