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Título: | Alkylammonium cation affinities of nitrogenated organobases: the roles of hydrogen bonding and proton transfer |
Fecha de publicación: | 12-jul-2021 |
Editorial: | Wiley |
Cita bibliográfica: | ChemPlusChem, 86 (8), 2021, 1097-1105 |
ISSN: | Electronic: 2192-6506 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica CDU::5 - Ciencias puras y naturales::54 - Química::543 - Química analítica |
Palabras clave: | Alkylammonium cation affinities Hydrogen Bonding and Proton Transfer DFT methods Nitrogen-containing organobases |
Resumen: | Alkylammonium cation affinities of 64 nitrogen-containing organobases, as well as the respective proton transfer processes from the alkylammonium cations to the base, have been computed in the gas phase by using DFT methods. The guanidine bases show the highest proton transfer values (191.9–233 kJ mol−1) whereas the cis-2,2’-biimidazole presents the largest affinity towards the alkylammonium cations (>200 kJ mol−1) values. The resulting data have been compared with the experimentally reported proton affinities of the studied nitrogen-containing organobases revealing that the propensity of an organobase for the proton transfer process increases linearly with its proton affinity. This work can provide a tool for designing senors for bioactive compounds containing amino groups that are protonated at physiological pH. |
Autor/es principal/es: | Sánchez Andrada, Pilar Vidal Vidal, Ángel Prieto, Tania Elguero, José Alkorta, Ibon Marin Luna, Marta |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202100235 |
URI: | http://hdl.handle.net/10201/138102 |
DOI: | https://doi.org/10.1002/cplu.202100235 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 9 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Descripción: | ©2021. This document is the Published version of a published Work that appeared in final form in ChemPlusChem. To access the final edited and published work see https://doi.org/10.1002/cplu.202100235 |
Aparece en las colecciones: | Artículos: Química Orgánica |
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