Isotriazene:  A Surprisingly Stable Minimum on the N₃H₃ Surface

On the Formation of N3H3 Isomers in Irradiated Ammonia Bearing Ices: Triazene (H2NNNH) or Triimide (HNHNNH)

“…These findings were refined by Pye et al . 1‐amino‐1,1‐diazene was first located on the potential energy surface by Salter et al., who suggested that this isomer (called isotriazene in their paper) is 42 to 50 kJ mol −1 lower in energy than cyclo‐triazane. Combined, these results show that the stabilities of triazenes decrease in the order trans ‐triazene, cis ‐triazene, triimide, 1‐amino‐1,1‐diazene and cyclo‐triazane (Scheme ).…”

Unprecedented Cyclic Isomer of Triazenes: A Computational Identification

“…N 3 R 3 belongs to a class of organic azides, for which the first member, phenyl azide was prepared as early as in 1864, and a large number of applications have been developed including peptide chemistry, combinatorial chemistry, and heterocyclic synthesis, etc. Ever since the first synthetic report in 1951, the N 3 R 3 family has very slowly grown into four known structural types, i.e., triazenes ( I ) with RN=N‐NR 2 moiety, triimides ( II ) with‐NR‐NR‐NR, iso‐triazenes ( III ) with R 2 N‐NR=N, and cyclo‐triazanes ( IV ) with c‐(NR) 3 in the decreased thermodynamic stability order. Amongst, the unique class of polyazo compounds triazenes ( I ) with three consecutive nitrogen atoms in an acyclic arrangement, i.e., ‐N=N‐N<, have received the most extensive studies.…”

“…The first laboratory study of N 3 H 3 was reported on the triazene isomer I in 1958 . A large number of computational studies have covered the structures, energetics and conversion of N 3 H 3 isomers at diversified levels of theory ,. Up to now, triazene I , triimide II and cyclo‐triazane IV have been identified in laboratory.…”

“…The diversity of a molecule in different geometrical forms contributes to the rich functions of our chemistry world. From 1951 to 1996, the N 3 R 3 family had very slowly gathered four members, i.e., triazenes ( I ) with RN=N‐NR 2 , triimides ( II ) with‐NR‐NR‐NR, iso‐triazenes ( III ) with R 2 N‐NR=N, and cyclo‐triazanes ( IV ) with c‐(NR) 3 . No new isomers have appeared from 1996 to present.…”

Ab initio quantum chemical computations of substituent effects on triaziridine strain energy and heat of formation

“…28 Additional studies have been carried out on a variety of triaziridine derivatives at various levels of theory. 9,11,[29][30][31][32][33][34][35][36][37] The present work focuses on assessing the heat of formation, ring strain energy, barriers to inversion of nitrogen, and magnetic properties, in the parent and as a function of N-substituents, with the hope of delving into issues of vincinal lone pair repulsion and aromatic stabilization in 1.…”