Computational study of the amination of halobenzenes and phenylpentazole. A viable route to isolate the pentazolate anion?
2004 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 69, no 9, 3222-3225 p.Article in journal (Refereed) Published
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+.
Place, publisher, year, edition, pages
2004. Vol. 69, no 9, 3222-3225 p.
polarizable continuum model, potassium-amide, molecules, n-4, derivatives, mechanism, solvation, entropies, chemistry, ammonia
IdentifiersURN: urn:nbn:se:kth:diva-23390DOI: 10.1021/jo035740fISI: 000221268200046ScopusID: 2-s2.0-2142821415OAI: oai:DiVA.org:kth-23390DiVA: diva2:342088
QC 201005252010-08-102010-08-102011-11-01Bibliographically approved