The mechanism of pyrolysis of 2-azidoethanol: A theoretical study.

Graphical abstract Highlights • Curtius-type rearrangement plays an important role in the pyrolysis reaction. • Two imine intermediates have been found in the pyrolysis reaction. • The most favorable products are HCHO, CH 2 NH, HCN, and N 2. Abstract The mechanism of thermal decomposition of 2-azidoethanol has been studied theoretically at a high and reliable level of theory (viz., CCSD(T)/aug-cc-pVTZ //MP2(full)/6-311++G(d,p)+0.95 × ZPE). The primary gas-phase decomposition channels of 2-azidoethanol have been put forward as follows: N 2 elimination from 2-azidoethanol leads to two imine intermediates CH 2 NCH 2 OH and CH 2 OHCH NH, followed by dissociation into the final products HCHO, CH 2 NH, HCN, N 2 and H 2. The calculated results are in qualitative agreement with the obtained experimental evidence. [ABSTRACT FROM AUTHOR]