Computational Study of the Amination of Halobenzenes and Phenylpentazole. A Viable Route to Isolate the Pentazolate Anion?

Amination of halobenzenes, which proceeds via
the benzyne intermediate (1), has been studied using
quantum chemical methods. The computational data are in
agreement with experimentally observed trends in reactivity
and provide a qualitative explanation for the observed
hydrogen isotope effects. To investigate if this is a viable
way to isolate the pentazolate anion (2), the reactivities of
the halobenzenes have been compared to phenylpentazole
(3). The reaction energetics for phenylpentazole become
favorable after complexation with Zn2+.