A DFT study on the structure–property relationship of amino-, nitro- and nitrosotetrazoles, and their N-oxides: new high energy density molecules

Abstract

We explore herein the structure, stability, heat of explosion, density, and the performance properties of amino, nitro, and nitroso substituted tetrazoles and their N-oxides using the density functional theory calculations at the B3LYP/aug-cc-pVDZ level. N-Nitro compounds have lower densities compared with those of C-nitrotetrazoles. Kamlet-Jacob semi-empirical equations were used to calculate the performance properties of designed compounds. The higher performance of tetrazole-N-oxides is due to their higher densities (2.110-2.287 g/cm 3 ). Heat of explosion, stability, density and performance properties are related to the number and relative positions of NO 2 , NH 2 , and NO groups of the tetrazole ring. The designed molecules satisfy the criteria of high energy materials.

Theoretical investigations on 4,4′,5,5′‐tetranitro‐2,2′‐1H,1′H‐2,2′‐biimidazole derivatives as potential nitrogen‐rich high energy materials

“…Geometry optimization of the molecular structures was carried out with the Gaussian 09 package . Semi‐empirical exchange–correlation functionals B3LYP with the aug‐cc‐pVDZ basis set has been successfully and widely used for predicting polynitrodiazoles compounds . All the optimized structures were positively identified to be true relative energy minima of the potential surfaces by frequency calculations (no imaginary frequencies were found).…”

“…Due to the high heat of formation (HOF), good thermal stability, low sensitivity and excellent detonation performance, nitroimidazoles have drawn renewed attention from explosive researchers currently . The geometric, thermodynamic and detonation properties of 4(5)‐nitroimidazole, 4,5‐dinitroimidazole (4,5‐DNI), 2,4‐dinitroimidazole (2,4‐DNI), amino‐ and methyl‐substituted trinitrodiazoles and aminonitroimidazoles have been already studied . However, most of experimental and theoretical studies were concentrated on monocyclic nitrodiazoles.…”

Computational Study on Structure and Properties of New Energetic Material 3,7-BIS(DINITROMETHYLENE)-2,4,6,8-TETRANITRO-2,4,6,8-TETRAAZA-BICYCLO[3.3.0]OCTANE

“…All computational details were performed on Gaussian 03 package 13 with the density functional theory (DFT) 14,15 at B3LYP method 16,17 with 6-31G (d,p) basis set. 18,19 Vibrational analyses at the same level of theory were performed to confirm that all of the optimized structures correspond to be the local energy minima on the potential energy surfaces.…”

Theoretical studies on structure and performance of [1,2,5]‐oxadiazolo‐[3,4‐d]‐pyridazine‐based derivatives

“…In order to meet the developing requirements of modern weapons and avoid the unintentional catastrophic explosives, searching for novel energetic compounds with better safety and performance becomes urgent and imperative . Because of the high heat of formation (HOF), high density, good molecular stability, and excellent detonation performance, nitrogen‐rich heterocyclic compounds have drawn attention from explosive researchers currently . Therein, [1,2,5]‐oxadiazolo‐[3,4‐ d ]‐ pyridazine derivatives have the potential to be high‐energy density materials (HEDMs) because of their good oxygen balance, high nitrogen contents, and high‐energy density.…”