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On the impact of a phosphoryl group in the recognition capabilities of 2-aminopyridines toward carboxylic acids

AuthorsGallegos, 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
Issue Date2019
PublisherSpringer Nature
CitationTheoretical Chemistry Accounts 138: 112 (2019)
AbstractInspired 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.
Publisher version (URL)https://doi.org/10.1007/s00214-019-2496-0
Identifiersdoi: 10.1007/s00214-019-2496-0
e-issn: 1432-2234
issn: 1432-881X
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