Arylpentazoles with surprisingly high kinetic stability

The more-than-one-century-old arylpentazoles can only be used in situ in generating the pentazole anion due to their unfavourable kinetic stability. We successfully increased the N 2 -leaving barrier to reach hitherto the highest value of 40.83 kcal mol −1 at the CBS-QB3 level via a newly proposed co-stabilization method, making the broader applications of arylpentazoles feasible. A co-stabilization method was proposed to design a series of novel arylpentazoles with very high N 2 -leaving barriers, one of which reached hitherto the highest value of 40.83 kcal mol −1 at the CBS-QB3 level.