Sulfur Groups Improve the Performance of Triazole- and Triazolium-Based Interaction Units in Anion Binding

An NMR comparative study of 1,2,3-triazole and triazolium anion recognition units containing sulfoxide, sulfone, and sulfoximine groups at C4 unveils an enhancement in binding ability up to ≈1 kcal/mol in acetone-d 6 correlated with a theoretical increase of H5 acidity. DFT calculations provide insi...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-03, Vol.82 (6), p.3341-3346
Main Authors: Álvarez-Pérez, Mónica, Velado, Marina, García-Puentes, Diego, Sáez, Elena, Vicent, Cristina, Fernández de la Pradilla, Roberto, Viso, Alma, de la Torre, María C, Sierra, Miguel A
Format: Article
Language:English
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Summary:An NMR comparative study of 1,2,3-triazole and triazolium anion recognition units containing sulfoxide, sulfone, and sulfoximine groups at C4 unveils an enhancement in binding ability up to ≈1 kcal/mol in acetone-d 6 correlated with a theoretical increase of H5 acidity. DFT calculations provide insight into binding modes in line with experimental data for these receptors.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00261