2024-03-28T23:28:07Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/2112922022-01-31T11:06:21Zcom_10261_28457com_10261_3col_10261_28462
On the impact of a phosphoryl group in the recognition capabilities of 2-aminopyridines toward carboxylic acids
Gallegos, Miguel
Gil-Guerrero, Sara
Fernández-Alarcón, A.
Bouzas-Ramos, Diego
Martín, Judith
Concellón, Carmen
Amo, Vicente del
Costa, J. M.
Mendoza-Meroño, R.
García-Granda, Santiago
Martín Pendás, Ángel
Costales, Aurora
Ministerio de Economía y Competitividad (España)
European Commission
Principado de Asturias
Consejo Nacional de Ciencia y Tecnología (México)
Inspired by natural molecular recognition processes, many research efforts have been routed in recent years toward the design of new host–guest molecular systems based on non-covalent interactions. Within this field, 2-aminopyridines (2APs) have been widely studied due to their tunable spectroscopic response in the presence of carboxylic acids. Herein, we present and analyze a novel family of 2AP core compounds based on 2-phosphorylamidopyridine (2PAP). Linear response time-dependent density functional theory (TD-DFT) has been used to characterize and model several spectroscopic properties of 2PAP. Our results, validated through experiments, show that TD-DFT can provide a reliable description of the electronic excited states of these aromatic systems. In addition, we have also studied the amino–imino tautomerization of 2AP and 2PAP in light of TD-DFT tools. We show that the presence of a carboxylic acid has a catalytic effect on the tautomerization reaction, which otherwise does not occur spontaneously at room temperature. These results suggest that this low-cost computational approach can be applied to more complex organic systems derived from 2-aminopyridine, paving the way for the development of potentially useful sensing materials and organic species for molecular recognition.
2020-05-13T12:16:22Z
2020-05-13T12:16:22Z
2019
2020-05-13T12:16:22Z
artículo
Theoretical Chemistry Accounts 138: 112 (2019)
http://hdl.handle.net/10261/211292
10.1007/s00214-019-2496-0
http://dx.doi.org/10.13039/501100003141
http://dx.doi.org/10.13039/501100003329
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/100011941
https://doi.org/10.1007/s00214-019-2496-0
Sí
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-65790-P
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-76829-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/RYC-2014-16021
closedAccess
Springer Nature