2026-04-17T09:41:40Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/43692022-12-19T09:42:07Zcom_10259_4354com_10259_5086com_10259_2604com_10259_4363col_10259_4355col_10259_4364

Fuertes Lázaro, Pedro 186 500 García Valverde, María 222 500 0000-0002-3990-8388 Pascual, Ricardo 419 600 Rodríguez Rodríguez, Mª Teresa 480 500 0000-0002-6375-1085 Rojo Cámara, Mª Josefa 485 500 0000-0002-8679-4707 García Calvo, José 198 500 0000-0002-1873-0293 Calvo Gredilla, Patricia 94 500 Cuevas Vicario, José Vicente 137 500 0000-0002-2421-1529 García Herbosa, Gabriel 205 500 0000-0002-2863-1272 Torroba Pérez, Tomás 554 500 0000-0002-5018-4173 2017-03-15T11:13:06Z 2017-03-15T11:13:06Z 2015-01 http://hdl.handle.net/10259/4369 The 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. Ministerio 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) application/pdf eng American Chemical Society Journal of Organic Chemistry (JOC). 2015, V. 80, n. 1, p. 30–39 http://dx.doi.org/10.1021/jo501473z info:eu-repo/grantAgreement/EC/FP7/312411 Chemistry, Organic Química orgánica Structural Conformers of (1,3-Dithiol-2-ylidene)ethanethioamides: The Balance Between Thioamide Rotation and Preservation of Classical Sulfur-Sulfur Hypervalent Bonds info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess THUMBNAIL Fuertes-JOC_2015.pdf.jpg Fuertes-JOC_2015.pdf.jpg IM Thumbnail image/jpeg 4756 https://riubu.ubu.es/bitstream/10259/4369/4/Fuertes-JOC_2015.pdf.jpg c5e3597bec7694eb7b633be3edccea23 MD5 4 ORIGINAL Fuertes-JOC_2015.pdf Fuertes-JOC_2015.pdf application/pdf 2268498 https://riubu.ubu.es/bitstream/10259/4369/1/Fuertes-JOC_2015.pdf 3da3223693bd82f87623edc996b5130b MD5 1 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/4369/2/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 2 TEXT Fuertes-JOC_2015.pdf.txt Fuertes-JOC_2015.pdf.txt Extracted text text/plain 68590 https://riubu.ubu.es/bitstream/10259/4369/3/Fuertes-JOC_2015.pdf.txt 904905cddfd490c9b3f351f4b8a6328f MD5 3 10259/4369 oai:riubu.ubu.es:10259/4369 2022-12-19 10:42:07.47 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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