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Theoretical Studies on the Mechanism of Hydrolysis of Nitroguanidine by AM1 Method
Author(s) -
Heming Xiao,
Yumin Li,
Yongfu Li
Publication year - 1998
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/(sici)1521-4087(199802)23:1<23::aid-prep23>3.0.co;2-2
Subject(s) - chemistry , hydrolysis , reagent , medicinal chemistry , nitrogen atom , ring (chemistry) , stereochemistry , polymer chemistry , computational chemistry , organic chemistry
The mechanism of hydrolysis of nitroguanidine has been studied theoretically. The molecular geometries have been fully optimized at AM1 level of theory for reagent, activated and product complexes for hydrolysis of nitroguanidine in neutral, acidic and alkaline media, respectively. In neutral and acidic media, both activated complexes have four‐membered ring structures, and the reaction‐coordinated eigenvectors show heavy‐atom reorganization and proton transfer to be truly concerted in both cases. In alkaline medium, the hydrolysis also involves activated complex. The calculated activation energies for the hydrolysis of nitroguanidine in neutral, acidic and alkaline media are 278.2 kJ/mol, 330.2 kJ/mol and 213.0 kJ/mol, respectively.