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Issue 22, 2011
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On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale

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Abstract

The azide–alkyne cycloaddition assisted by a self-assembled molecular flask developed by Rebek and coworkers (Org. Lett., 2002, 4, 327) has been simulated by means of the ONIOM methodology, thereby evidencing the reliability of this theoretical approach to model such large encapsulated systems. Experimental evidences accounting for this transformation within the supramolecular assembly such as the significant rate enhancement, complete regioselectivity, and product inhibition as the reaction proceeds have been qualitatively disentangled through estimation of the energy barriers and the structural characteristics of the corresponding host–guest complexes.

Graphical abstract: On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale

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Publication details

The article was received on 19 Jul 2011, accepted on 31 Aug 2011 and first published on 31 Aug 2011


Article type: Communication
DOI: 10.1039/C1OB06206A
Org. Biomol. Chem., 2011,9, 7638-7642

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    On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale

    D. Cantillo, M. Ávalos, R. Babiano, P. Cintas, J. L. Jiménez and J. C. Palacios, Org. Biomol. Chem., 2011, 9, 7638
    DOI: 10.1039/C1OB06206A

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