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Synthesis, Spectroscopic and Thermal Characterization of Azido‐1,2,4‐triazoles: A Class of Heteroarenes with a High Nitrogen Content
Author(s) -
Cardillo Paolo,
Dellavedova Marco,
Gigante Lucia,
Lunghi Angelo,
Pasturenzi Christian,
Salatelli Elisabetta,
Zanirato Paolo
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101450
Subject(s) - chemistry , trifluoroacetic acid , formic acid , mass spectrometry , reactivity (psychology) , thermal decomposition , hydrochloride , acetic acid , tautomer , nitrogen , organic chemistry , computational chemistry , analytical chemistry (journal) , chromatography , medicine , alternative medicine , pathology
The syntheses of azido‐1,2,4‐triazoles 1 – 5 were carried out from triaminoguanidine hydrochloride and a carboxylic acid (formic, acetic, 2,2,2‐trifluoroacetic, 2‐benzylacetic, monochloroacetic acid) by a three‐step synthetic route and were analyzed by accelerating rate calorimetry (ARC). The thermal decomposition of 1 – 5 was studied theoretically by using CHETAH and T1 software, and experimentally by using DSC to obtain kinetic data. Numerical modelling and mass spectrometry were also performed to estimate the nature of the intrinsic molecular reactivity of 1 – 5 and the possible early stages of a self‐heating process. Complete optimization by using HF, B3LYP and MP2(full) methods at the 6‐31G* level were performed on significant tautomeric forms of the azido‐triazoles to confirm the electronic structures that were obtained by EI‐MS.