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Abstract:

A combination of NMR spectroscopy and theoretical methods Density functional theory including dispersion corrections (DFT-D) was used to study the structures of Lumogen and salicylaldazine. In the solid state, Lumogen exists as the dihydroxy tautomer 1a (an azine, Cï£N-Nï£C) as was already known from an X-ray determination. In a deuterated dimethyl sulfoxide solution, another tautomer is observed besides 1a; its structure corresponds to the hydroxy-oxo tautomer 1b (a hydrazone, Cï£N-NH-Csp2). In what concerns salicylaldazine, we have observed only the dihydroxy tautomer 2a. Copyright © 2013 John Wiley & Sons, Ltd.

Registro:

Documento: Artículo
Título:The structures of two aldazines: [1,1′-(1E,1′E)-hydrazine-1,2- diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2′-(1E,1′E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene) diphenol (salicylaldazine) in the solid state and in solution
Autor:Silva, A.M.S.; Silva, V.L.M.; Claramunt, R.M.; María, D.S.; Ferraro, M.B.; Reviriego, F.; Alkorta, I.; Elguero, J.
Filiación:Chemistry Department and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal
Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, Universidad Nacional de Educaciõn A Distancia (UNED), Senda del Rey 9, E-28040 Madrid, Spain
Departamento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires and IFIBA, 1428 Buenos Aires, Argentina
Instituto de Química Médica, Centro de Química Orgánica Manuel Lora-Tamayo, IQM-CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain
Palabras clave:CPMAS; DFT-D calculations; Lumogen; NMR; salicylaldazine; temperature effects; drug derivative; hydrazine derivative; naphthol derivative; thioridazine; article; chemical structure; chemistry; CPMAS; DFT-D calculations; Lumogen; nuclear magnetic resonance; nuclear magnetic resonance spectroscopy; quantum theory; salicylaldazine; solution and solubility; temperature effects; X ray crystallography; CPMAS; DFT-D calculations; Lumogen; NMR; salicylaldazine; temperature effects; Crystallography, X-Ray; Hydrazines; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; Naphthols; Quantum Theory; Solutions; Thioridazine
Año:2013
Volumen:51
Número:9
Página de inicio:530
Página de fin:540
DOI: http://dx.doi.org/10.1002/mrc.3983
Título revista:Magnetic Resonance in Chemistry
Título revista abreviado:Magn. Reson. Chem.
ISSN:07491581
CODEN:MRCHE
CAS:thioridazine, 130-61-0, 50-52-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v51_n9_p530_Silva

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Citas:

---------- APA ----------
Silva, A.M.S., Silva, V.L.M., Claramunt, R.M., María, D.S., Ferraro, M.B., Reviriego, F., Alkorta, I.,..., Elguero, J. (2013) . The structures of two aldazines: [1,1′-(1E,1′E)-hydrazine-1,2- diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2′-(1E,1′E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene) diphenol (salicylaldazine) in the solid state and in solution. Magnetic Resonance in Chemistry, 51(9), 530-540.
http://dx.doi.org/10.1002/mrc.3983
---------- CHICAGO ----------
Silva, A.M.S., Silva, V.L.M., Claramunt, R.M., María, D.S., Ferraro, M.B., Reviriego, F., et al. "The structures of two aldazines: [1,1′-(1E,1′E)-hydrazine-1,2- diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2′-(1E,1′E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene) diphenol (salicylaldazine) in the solid state and in solution" . Magnetic Resonance in Chemistry 51, no. 9 (2013) : 530-540.
http://dx.doi.org/10.1002/mrc.3983
---------- MLA ----------
Silva, A.M.S., Silva, V.L.M., Claramunt, R.M., María, D.S., Ferraro, M.B., Reviriego, F., et al. "The structures of two aldazines: [1,1′-(1E,1′E)-hydrazine-1,2- diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2′-(1E,1′E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene) diphenol (salicylaldazine) in the solid state and in solution" . Magnetic Resonance in Chemistry, vol. 51, no. 9, 2013, pp. 530-540.
http://dx.doi.org/10.1002/mrc.3983
---------- VANCOUVER ----------
Silva, A.M.S., Silva, V.L.M., Claramunt, R.M., María, D.S., Ferraro, M.B., Reviriego, F., et al. The structures of two aldazines: [1,1′-(1E,1′E)-hydrazine-1,2- diylidenebis(methan-1-yl-1-ylidene)dinaphthalen-2-ol] (Lumogen) and 2,2′-(1E,1′E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene) diphenol (salicylaldazine) in the solid state and in solution. Magn. Reson. Chem. 2013;51(9):530-540.
http://dx.doi.org/10.1002/mrc.3983