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dc.contributor.authorFuertes Lázaro, Pedro 
dc.contributor.authorGarcía Valverde, María 
dc.contributor.authorPascual, Ricardo 
dc.contributor.authorRodríguez Rodríguez, Mª Teresa 
dc.contributor.authorRojo Cámara, Mª Josefa 
dc.contributor.authorGarcía Calvo, José 
dc.contributor.authorCalvo, Patricia 
dc.contributor.authorCuevas Vicario, José Vicente 
dc.contributor.authorGarcía Herbosa, Gabriel 
dc.contributor.authorTorroba Pérez, Tomás 
dc.date.accessioned2017-03-15T11:13:06Z
dc.date.available2017-03-15T11:13:06Z
dc.date.issued2015-01
dc.identifier.urihttp://hdl.handle.net/10259/4369
dc.description.abstractThe reaction of N-(2-phthalimidoethyl)-N-alkylisopropylamines and S2Cl2 gave 4-N-(2-phthalimidoethyl)-N-alkylamino-5-chloro-1,2-dithiol-3-thiones that quantitatively cycloadded to dimethyl or diethyl acetylenedicarboxylate to give stable thioacid chlorides, which in turn reacted with one equivalent of aniline or a thiole to give thioanilides or a dithioester. Several compounds of this series showed atropisomers that were studied by a combination of dynamic NMR, simulation of the signals, conformational analysis by DFT methods, and single crystal X-ray diffraction, showing a good correlation between the theoretical calculations, the experimental values of energies, and the preferred conformations in the solid state. The steric hindering of the crowded substitution at the central amine group was found to be the reason for the presence of permanent atropisomers in this series of compounds and the cause of a unique disposition of the thioxo group at close-to-right angles with respect to the plane defined by the 1,3-dithiole ring in the dithiafulvene derivatives, thus breaking the sulfur–sulfur hypervalent bond that is always found in this kind of compounds.en
dc.description.sponsorshipMinisterio de Economıá y Competitividad, Spain (Project CTQ2012- 31611), Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo (Project BU246A12-1), and the European Commission, Seventh Framework Programme (Project SNIFFER FP7-SEC-2012-312411)en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherAmerican Chemical Societyen
dc.relation.ispartofJournal of Organic Chemistry (JOC). 2015, V. 80, n. 1, p. 30–39en
dc.titleStructural Conformers of (1,3-Dithiol-2-ylidene)ethanethioamides: The Balance Between Thioamide Rotation and Preservation of Classical Sulfur-Sulfur Hypervalent Bondsen
dc.typeArtículoes
dc.typeinfo:eu-repo/semantics/article
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttp://dx.doi.org/10.1021/jo501473z
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/312411
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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