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Mechanisms of tetrazole formation by addition of azide to nitriles
2002 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 124, no 41, 12210-12216 p.Article in journal (Refereed) Published
Abstract [en]

It is well-known that azide salts can engage nitriles at elevated temperatures to yield tetrazoles; however, there is continued debate as to the mechanism of the reaction. Density functional theory calculations with the hybrid functional B3LYP have been performed to study different mechanisms of tetrazole formation, including concerted cycloaddition and stepwise addition of neutral or anionic azide species. The calculations presented here suggest a previously unsuspected nitrile activation step en route to an imidoyl azide, which then cyclizes to give the tetrazole. The activation barriers are found to correlate strongly with the electron-withdrawing potential of the substituent on the nitrile.

Place, publisher, year, edition, pages
2002. Vol. 124, no 41, 12210-12216 p.
Keyword [en]
5-substituted tetrazoles, exchange, model
URN: urn:nbn:se:kth:diva-21960ISI: 000178514700040OAI: diva2:340658
QC 20100525Available from: 2010-08-10 Created: 2010-08-10Bibliographically approved

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Himo, Fahmi
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