Identificador persistente para citar o vincular este elemento:
http://hdl.handle.net/10662/21890
Títulos: | Imine or Enamine? Insights and Predictive Guidelines from the Electronic Effect of Substituents in H‑Bonded Salicylimines |
Autores/as: | Martínez Vázquez, Rafael Fernando Matamoros Castellano, Esther Cintas Moreno, Pedro Palacios Albarrán, Juan Carlos |
Palabras clave: | Aromatic compounds;Substituents;Noncovalent interactions;Compuestos aromáticos;Sustituyentes;Interacciones no covalentes |
Fecha de publicación: | 2020 |
Editor/a: | ACS Publications |
Resumen: | Imine and enamine bonds decorate the skeleton of numerous reagents, catalysts, and organic materials. However, it is difficult to isolate at will a single tautomer, as dynamic equilibria occur easily, even in the solid state, and are sensitive to electronic and steric effect, including π-conjugation and H-bonding. Here, using as model Schiff bases generated from salicylaldehydes and TRIS in a set of linear free energy relationships (LFER), we disclose how the formation of either imines or enamines can be controlled and provide a comprehensive framework that captures the structural underpinning of this prediction. This work highlights the potentiality of tailor-made designs en route to compounds with desirable functionality. |
Descripción: | Publicado en: J. Org. Chem. 2020, 85, 9, 5838–5862 con DOI https://doi.org/10.1021/acs.joc.0c00130 |
URI: | http://hdl.handle.net/10662/21890 |
ISSN: | 0022-2623 |
Colección: | DQOIN - Artículos IACYS - Artículos |
Archivos
Archivo | Descripción | Tamaño | Formato | |
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acs_joc_0c00130_draft.pdf | 845,06 kB | Adobe PDF | Descargar |
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