Alkylammonium cation affinities of nitrogenated organobases: the roles of hydrogen bonding and proton transfer

Sánchez Andrada, Pilar; Vidal Vidal, Ángel; Prieto, Tania; Elguero, José; Alkorta, Ibon; Marin Luna, Marta

Publication:
Alkylammonium cation affinities of nitrogenated organobases: the roles of hydrogen bonding and proton transfer

dc.contributor.author	Sánchez Andrada, Pilar
dc.contributor.author	Vidal Vidal, Ángel
dc.contributor.author	Prieto, Tania
dc.contributor.author	Elguero, José
dc.contributor.author	Alkorta, Ibon
dc.contributor.author	Marin Luna, Marta
dc.contributor.department	Química Orgánica
dc.date.accessioned	2024-01-30T08:59:48Z
dc.date.available	2024-01-30T08:59:48Z
dc.date.issued	2021-07-12
dc.description	©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
dc.description.abstract	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.	es
dc.format	application/pdf	es
dc.format.extent	9	es
dc.identifier.citation	ChemPlusChem, 86 (8), 2021, 1097-1105
dc.identifier.doi	https://doi.org/10.1002/cplu.202100235
dc.identifier.issn	Electronic: 2192-6506
dc.identifier.uri	http://hdl.handle.net/10201/138102
dc.language	eng	es
dc.publisher	Wiley	es
dc.relation	This work was carried out with financial support from the Spanish MICINN for financial support (projects CTQ2018-094644-B-C22 and CTQ2017-87231-P and PID2020-113686GB-I00), Comunidad de Madrid (P2018/EMT-4329 AIRTEC-CM), and the Fundación Seneca-CARM (Project 20811/PI/18).	es
dc.relation.publisherversion	https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202100235	es
dc.rights	info:eu-repo/semantics/openAccess	es
dc.rights	Attribution-NonCommercial-NoDerivatives 4.0 Internacional	*
dc.rights.uri	http://creativecommons.org/licenses/by-nc-nd/4.0/	*
dc.subject	Alkylammonium cation affinities	es
dc.subject	Hydrogen Bonding and Proton Transfer	es
dc.subject	DFT methods	es
dc.subject	Nitrogen-containing organobases	es
dc.subject.other	CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica	es
dc.subject.other	CDU::5 - Ciencias puras y naturales::54 - Química::543 - Química analítica	es
dc.title	Alkylammonium cation affinities of nitrogenated organobases: the roles of hydrogen bonding and proton transfer	es
dc.type	info:eu-repo/semantics/article	es
dspace.entity.type	Publication	es