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Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts?
KTH, Superseded Departments, Biotechnology.
2003 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, no 33, 9983-9987 p.Article in journal (Refereed) Published
Abstract [en]

The mechanism by which zinc(II) catalyzes the union of an azide ion with organic nitriles to form tetrazoles is investigated by means of density functional theory using the hybrid functional B3LYP. The calculations indicate that coordination of the nitrile to the zinc ion is the dominant factor affecting the catalysis; this coordination substantially lowers the barrier for nucleophilic attack by azide. Relative reaction rates of catalyzed and uncatalyzed tetrazole formation also provide experimental support for this conclusion.

Place, publisher, year, edition, pages
2003. Vol. 125, no 33, 9983-9987 p.
Keyword [en]
5-substituted tetrazoles, amino-acids, cycloadditions, rearrangement, mechanisms, exchange, origins, model, route
URN: urn:nbn:se:kth:diva-22748DOI: 10.1021/ja030204qISI: 000184779100032OAI: diva2:341446
QC 20100525Available from: 2010-08-10 Created: 2010-08-10Bibliographically approved

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