NDLI: A comparative theoretical study on energetic substituted 1,2,3- and 1,2,4-triazoles: the azido-cyclization mechanism and the effect of solvent

Content Provider	Royal Society of Chemistry (RSC)
Author	He, Piao Zhang, Jian-Guo Zhang, Shaowen Jin, Xin Yin, Xin Wang, Kun Zhang, Tong-Lai
Copyright Year	2015
Abstract	The hybrid DFT calculations with B3LYP/6-311G* level of theory have allowed us to gain insight into the azido-cyclization of 4,5-diazido-1,2,3-triazole and 3,5-diazido-1,2,4-triazole and the effect of solvent. The optimized geometry, charges and molecular electrostatic potential were calculated and the results indicate that the cyclization occurs mainly in the conversion azido → tetrazole, in which the molecular and electronic structures change more significantly. Further analysis of the energy parameters indicates that all possible reactions are endothermic and not spontaneous in the gas phase, but the first and second azido-cyclization of 3,5-diazido-1,2,4-triazole could be performed theoretically with energy barriers of 26 kcal mol−1 and 33 kcal mol−1. Again, the rate constants and the Arrhenius experience formula of azido-cyclization have been obtained between 200–1000 K temperature regions. In addition, the solvent effect on azido-cyclization was studied with acetone, trifluoroacetic acid and dimethylsulfoxide. The results show that the solvent effect can make the intermediates and products more stable than in the gas phase. The energy barriers for the first and second cyclization are lowered more or less especially in dimethylsulfoxide, and the influence on the azido-cyclization of 4,5-diazido-1,2,3-triazole is a little larger.
Starting Page	3882
Ending Page	3888
Page Count	7
File Format	HTM / HTML PDF
ISSN	11440546
Volume Number	39
Issue Number	5
Journal	New Journal of Chemistry
DOI	10.1039/c4nj01781a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Arrhenius Endothermic process Triazole Carboxylic acid Tetrazole Dimethyl sulfoxide Arrhenius equation 1,2,3-Triazole Solvent Electrostatics Molecular geometry Acetone
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Chemistry Catalysis

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