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Substituent Pattern Effect in the reaction of dimethyltrinitronaphthalenes with Di‐ and triethylamine
Author(s) -
Buckley E.,
Houiellebecq T. F.,
Wells C. H. J.
Publication year - 1984
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.19840090404
Subject(s) - triethylamine , substituent , methanol , kinetics , solvent , chemistry , base (topology) , explosive material , photochemistry , medicinal chemistry , organic chemistry , physics , mathematical analysis , mathematics , quantum mechanics
The kinetics of the reaction of di‐ and triethylamine with 1,8‐dimethyl‐2,4,5‐trinitronaphthalene (245 TND) have been studied in dimethylsulfoxide and dimethylsulfoxide‐methanol solvent systems and comparison made with data for corresponding reactions involving 1,5‐dimethyl‐2,4,8‐trinitronaphthalene (248 TND). Analysis of the results shows that the formation of a benzyl‐type anion is more facile with 245 TND than with 248 TND. Thus, the former compound has the greater potential for base‐induced coupling to give thermally stable explosive material.