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10.1021/acs.joc.8b02496
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Título: | Exploring the Conversion of Macrocyclic 2,2 '-Biaryl Bis(thioureas) into Cyclic Monothioureas: An Experimental and Computational Investigation |
Fecha de publicación: | 23-oct-2018 |
Fecha de defensa / creación: | 2018 |
Editorial: | American Chemical Society |
Cita bibliográfica: | J. Org. Chem. 2018, 83, 14022–14035. |
ISSN: | 0022-3263 1520-6904 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | DIFFUSION MEASUREMENTS NMR-SPECTROSCOPY DFT CALCULATIONS MACROCYCLES SYNTHESIS |
Resumen: | Macrocyclic bis(thioureas) derived from 2,2’-biphenyl and binaphthyl skeletons have been synthesized by reaction of 2,2’-diaminobiaryl and 2,2’-bis(isothiocyanato)biaryl derivatives. The splitting of these bis(thioureas) into two units of the respective cyclic monothioureas has been monitored by NMR, shedding some light on the factors that control these processes. Additionally, a computational study revealed up to three mechanistic paths for the conversion of the 2,2’-biphenyl-derived bis(thiourea) into the corresponding monothiourea. The proposed mechanisms account for the participation of a molecule of water as an efficient proton-switch, as well as for different classes of putative intermediates. The computational study also supports the ability of the thiourea group to participate in a plethora of processes, such as prototropic equilibria, sigmatropic shifts, heteroene and retro-heteroene reactions, and cis-trans isomerizations. |
Autor/es principal/es: | Alajarín, Mateo Lopez-Leonardo, Carmen Orenes, Raul A. Pastor Vivero, Aurelia Sanchez-Andrada, Pilar Vidal, Angel |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://pubs.acs.org/doi/10.1021/acs.joc.8b02496 |
URI: | http://hdl.handle.net/10201/102581 |
DOI: | 10.1021/acs.joc.8b02496 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 21 |
Derechos: | info:eu-repo/semantics/openAccess Atribución-NoComercial-SinDerivadas 3.0 España |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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18JOC_AV-Macrocyclic Thioureas.pdf | 1,58 MB | Adobe PDF | Visualizar/Abrir |
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