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Relative rates of Hydrolysis of Nitro‐ and Fluoro‐Substituted Esters
Author(s) -
Cichra D. A.,
Adolph H. G.
Publication year - 1987
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.19870120605
Subject(s) - hydrolysis , nitro , chemistry , alkyl , acetonitrile , medicinal chemistry , organic chemistry , acid hydrolysis , molecule
Abstract Relative hydrolysis rates were determined for a series of 14 nitrosubstituted esters and some comparison compounds in 75/25 acetonitrile/water at 75.3°C. The nitroalkyl esters were found to undergo unexpectedly rapid hydrolysis relative to other negatively substituted alkyl esters such as fluoroalkyl. To explain this result, participation of the nitro group in the hydrolysis, especially in the case of trinitromethyl compounds, is postulated. Nitro groups in the acid portion of the ester molecule can increase or decrease the reactivtiy towards hydrolysis, depending on the site of substitution.