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Density functional theory study of the intramolecular 2+3 cycloaddition of azide to nitriles
KTH, Superseded Departments, Biotechnology.
2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 23, 9076-9080 p.Article in journal (Refereed) Published
Abstract [en]

Density functional theory calculations using the hybrid functional B3LYP have been performed to study tetrazole formation by intramolecular [2 + 3] dipolar cycloaddition of organic azides and nitriles. Experimental reactivity trends are explained and rationalized in terms of a number of parameters, such as strain, tether length, and solvation and entropy effects. Interestingly, no correlation was found between the overall free energies and the free energies of activation of the reactions, due to the significant difference in strain and geometry between the transition states and products.

Place, publisher, year, edition, pages
2003. Vol. 68, no 23, 9076-9080 p.
Keyword [en]
huisgen 1,3-dipolar cycloaddition, click chemistry approach, aryl azides, tetrazoles, exchange, cyanides, model, ring
Identifiers
URN: urn:nbn:se:kth:diva-22949DOI: 10.1021/jo030137iISI: 000186489000044OAI: oai:DiVA.org:kth-22949DiVA: diva2:341647
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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