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Exploring the Conversion of Macrocyclic 2,2 '-Biaryl Bis(thioureas) into Cyclic Monothioureas: An Experimental and Computational Investigation

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dc.contributor.authorAlajarín, Mateo
dc.contributor.authorLopez-Leonardo, Carmen
dc.contributor.authorOrenes, Raul A.
dc.contributor.authorPastor Vivero, Aurelia
dc.contributor.authorSanchez-Andrada, Pilar
dc.contributor.authorVidal, Angel
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-02-04T06:05:54Z
dc.date.available2021-02-04T06:05:54Z
dc.date.created2018
dc.date.issued2018-10-23
dc.description.abstractMacrocyclic 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.es
dc.formatapplication/pdfes
dc.format.extent21es
dc.identifier.citationJ. Org. Chem. 2018, 83, 14022–14035.
dc.identifier.doi10.1021/acs.joc.8b02496
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/10201/102581
dc.languageenges
dc.publisherAmerican Chemical Societyes
dc.relation(I) Ministerio de Economía, Industria y Competitividad. Programa Estatal de Fomento de la Investigación Científica y Técnica de Excelencia. Proyectos I+D 2017 (Nacional). Nombre del proyecto: Reactividad y Conmutación de Moléculas Mecanizadas. Código: CTQ2017-87231-P. (II) Fundación Séneca (Comunidad Autónoma de la Región de Murcia). Ayudas para la realización de proyectos de investigación destinadas a grupos competitivos (Programa Séneca 2014) (Regional). Nombre del proyecto: Cicloadiciones de Ceteniminas Catalizadas por Metales de Transición y Reacciones de Ceteniminas con Carbenos Nucleofílicos y Bencino. Conmutación y Organización Tridimensional de Moléculas Entrelazadas. Código: 19240/PI/14.es
dc.relation.isreplacedbyhttps://doi.org/10.1021/acs.joc.8b02496es
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.8b02496es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectDIFFUSION MEASUREMENTSes
dc.subjectNMR-SPECTROSCOPYes
dc.subjectDFT CALCULATIONSes
dc.subjectMACROCYCLESes
dc.subjectSYNTHESISes
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleExploring the Conversion of Macrocyclic 2,2 '-Biaryl Bis(thioureas) into Cyclic Monothioureas: An Experimental and Computational Investigationes
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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