Please use this identifier to cite or link to this item:
http://hdl.handle.net/10662/21890
Title: | Imine or Enamine? Insights and Predictive Guidelines from the Electronic Effect of Substituents in H‑Bonded Salicylimines |
Authors: | Martínez Vázquez, Rafael Fernando Matamoros Castellano, Esther Cintas Moreno, Pedro Palacios Albarrán, Juan Carlos |
Keywords: | Aromatic compounds;Substituents;Noncovalent interactions;Compuestos aromáticos;Sustituyentes;Interacciones no covalentes |
Issue Date: | 2020 |
Publisher: | ACS Publications |
Abstract: | 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. |
Description: | 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 |
Appears in Collections: | DQOIN - Artículos IACYS - Artículos |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
acs_joc_0c00130_draft.pdf | 845,06 kB | Adobe PDF | View/Open |
This item is licensed under a Creative Commons License