Quantum Chemical Prediction of Equilibrium Acidities of Ureas, Deltamides, Squaramides, and Croconamides.

Ho, Junming; Zwicker, Vincent E; Yuen, Karen K Y; Jolliffe, Katrina A

Ho, Junming; Zwicker, Vincent E; Yuen, Karen K Y; Jolliffe, Katrina A.

Afiliación

Ho J; School of Chemistry, University of New South Wales , Sydney, NSW 2052, Australia.
Zwicker VE; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
Yuen KKY; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
Jolliffe KA; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.

J Org Chem ; 82(19): 10732-10736, 2017 10 06.

Article en En | MEDLINE | ID: mdl-28832145

RESUMEN

Robust quantum chemical methods are employed to predict the pKa's of several families of dual hydrogen-bonding organocatalysts/anion receptors, including deltamides and croconamides as well as their thio derivatives. The average accuracy of these predictions is â¼1 pKa unit and allows for a comparison of the acidity between classes of receptors and for quantitative studies of substituent effects. These computational insights further explain the relationship between pKa and chloride anion affinity of these receptors that will be important for designing future anion receptors and organocatalysts.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Prognostic_studies / Risk_factors_studies Idioma: En Revista: J Org Chem Año: 2017 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Estados Unidos

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