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Danese M, Bon M, Piccini G, et al. The reaction mechanism of the azide-alkyne Huisgen cycloaddition. Phys Chem Chem Phys. 2019;21(35):19281-19287doi: 10.1039/c9cp02386k.
Danese, M., Bon, M., Piccini, G., & Passerone, D. (2019). The reaction mechanism of the azide-alkyne Huisgen cycloaddition. Physical chemistry chemical physics : PCCP, 21(35), 19281-19287. https://doi.org/10.1039/c9cp02386k
Danese, Martina, et al. "The reaction mechanism of the azide-alkyne Huisgen cycloaddition." Physical chemistry chemical physics : PCCP vol. 21,35 (2019): 19281-19287. doi: https://doi.org/10.1039/c9cp02386k
Danese M, Bon M, Piccini G, Passerone D. The reaction mechanism of the azide-alkyne Huisgen cycloaddition. Phys Chem Chem Phys. 2019 Sep 11;21(35):19281-19287. doi: 10.1039/c9cp02386k. PMID: 31451823.
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Phys Chem Chem Phys. 2019 Sep 11;21(35):19281-19287. doi: 10.1039/c9cp02386k.

The reaction mechanism of the azide-alkyne Huisgen cycloaddition.

Physical chemistry chemical physics : PCCP

Martina Danese, Marta Bon, GiovanniMaria Piccini, Daniele Passerone

Affiliations

  1. Empa, Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland. [email protected].
  2. Department of Chemistry and Applied Bioscience, ETH Zurich, c/o USI Campus, Lugano, Switzerland.

PMID: 31451823 DOI: 10.1039/c9cp02386k

Abstract

The azide-alkyne Huisgen cycloaddition has a key role in click chemistry and is configured as a powerful tool in pharmaceutical and medicinal chemistry. Although this reaction has already been largely studied, there is an ongoing debate about its mechanism. In this work we study the dynamical aspects of the process using metadynamics computer simulations. We focus on the conformational aspects that determine the course of the reaction and characterize its free energy landscape. To properly capture the thermodynamics of the process we select optimal collective variables using harmonic linear discriminant analysis. The results qualitatively confirm and explain the experimental evidence and give insights into the role of the substituents and the possible transition mechanisms.

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