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Reaction of carboxylic acids with isocyanides: A mechanistic DFT study
KTH, School of Biotechnology (BIO), Theoretical Chemistry.
2008 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 28, 4751-4754 p.Article in journal (Refereed) Published
Abstract [en]

We present a computational investigation of the reaction between isocyanides and carboxylic acids. Our results indicate that this reaction begins with a stereoselective concerted alpha-addition of the acid to the isocyanide, leading exclusively to a Z-acyl imidate. Isomerization to the E isomer and successive rate-limiting 1,3 O -> N acyl migration yields an N-formyl imide. The calculated barriers are in good agreement with the experimental reaction conditions. Our results might provide an explanation for the peculiar reactivity observed when this reaction is carried out in a self-assembled capsule. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

Place, publisher, year, edition, pages
2008. no 28, 4751-4754 p.
Keyword [en]
density functional calculations, isocyanides, reaction mechanisms, E/Z, isomerism, glycosylation, density-functional thermochemistry, anionic 1,1-addition, hydrogen, isocyanide, exchange, isonitriles, energies, model
Identifiers
URN: urn:nbn:se:kth:diva-17888DOI: 10.1002/ejoc.200800710ISI: 000260038000003Scopus ID: 2-s2.0-53849124717OAI: oai:DiVA.org:kth-17888DiVA: diva2:335933
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved

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