Premium
Synthesis, Characterization and Energetic Properties of 1,3,4‐Oxadiazoles
Author(s) -
Wang Zuoquan,
Zhang Hong,
Killian Benjamin J.,
Jabeen Farukh,
Pillai Girinath G.,
Berman Heather M.,
Mathelier Michael,
Sibble Ashani J.,
Yeung Justin,
Zhou Wenfeng,
Steel Peter J.,
Hall C. Dennis,
Katritzky Alan R.
Publication year - 2015
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.201500583
Subject(s) - chemistry , detonation , detonation velocity , standard enthalpy of formation , nitro , combustion , molecule , planarity testing , organic chemistry , crystallography , explosive material , alkyl
An efficient cyclization between nitro‐substituted benzoic acids and nitro‐substituted benzohydrazides affords 1,3,4‐oxadiazoles. Facile synthesis and a broad substrate scope produce a range of compounds, some of them with potential as high‐energy compounds. Heats of formation (Δ H f ) and densities ( ρ ) were calculated, and heats of decomposition (Δ H d ) and combustion (Δ H c ) were determined experimentally. The densities of seven of the synthesized compounds were determined by gas pycnometry, and the respective values of detonation velocity ( V D ), detonation pressure ( P D ) and specific impulse ( I SP ) were calculated using the EXPLO5 program. An X‐ray structure of 2‐(2,4‐dinitrophenyl)‐5‐(3,5‐dinitrophenyl)‐1,3,4‐oxadiazole ( 4n ) revealed the non‐planarity of the molecule and afforded a crystal density of 1.698 (at 120 K), close to the pycnometric value of 1.64 at room temperature.