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Kinetic study of the nitrosation of 1,3-dialkylureas in aqueous-perchloric acid medium

✍ Scribed by Guillermo González-Alatorre; Salvador H. Guzmán-Maldonado; Eleazar M. Escamilla-Silva; Guadalupe Loarca-Piña; Carlos Hernández Benítez

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
119 KB
Volume
36
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The kinetics of the nitrosation of 1,3‐dimethyl (DMU), 1,3‐diethyl (DEU), 1,3‐dipropylurea (DPU), 1,3‐dibuthyl (DBU), and 1,3‐diallylurea (DAU) were studied in a conventional UV/vis spectrophotometer in aqueous‐perchloric acid media. The kinetic study was carried out using the initial rate method. The reaction rate observed was

equation image

where K~a~ is the acidity constant of nitrous acid. The diureas exhibited the reactivity order DMU ≫ DEU > DPU > DAU, which can be interpreted as a function of the steric impediment generated by the R alkyl group in the rate controlling step. A probable relationship between both the chemical reactivity and structure of the nitrosable substrate with the biological activity of the N‐nitroso compounds generated is proposed. © 2004 Wiley Periodicals, Inc. Int J Chem Kinet 36: 273–279, 2004

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