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
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 fro...
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2013
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| LEADER | 12627caa a22017417a 4500 | ||
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| 001 | PAPER-11295 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250314095715.0 | ||
| 008 | 190411s2013 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84881474139 | |
| 024 | 7 | |2 cas |a thioridazine, 130-61-0, 50-52-2 | |
| 030 | |a MRCHE | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Silva, A.M.S. | |
| 245 | 1 | 4 | |a 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 |
| 260 | |c 2013 | ||
| 270 | 1 | 0 | |m María, D.S.; 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; email: dsanta@ccia.uned.es |
| 504 | |a Arnal, E., Elguero, J., Jacquier, R., Marzin, C., Wilde, J., (1966) Bull. Soc. Chim. Fr., p. 877 | ||
| 504 | |a Elguero, J., Jacquier, R., Marzin, C., (1966) Bull. Soc. Chim. Fr., p. 2132 | ||
| 504 | |a Elguero, J., Jacquier, R., Marzin, C., (1966) Bull. Soc. Chim. Fr., p. 3005 | ||
| 504 | |a Berthou, J., Elguero, J., Jacquier, R., Marzin, C., Rérat, C., (1967) Compt. Rend. Acad. Sci. (Paris), 265 C, p. 513 | ||
| 504 | |a Elguero, J., Jacquier, R., Marzin, C., (1968) Bull. Soc. Chim. Fr., p. 713 | ||
| 504 | |a Elguero, J., Jacquier, R., Marzin, C., (1969) Bull. Soc. Chim. Fr., p. 1367 | ||
| 504 | |a Elguero, J., Jacquier, R., Marzin, C., (1969) Bull. Soc. Chim. Fr., p. 1374 | ||
| 504 | |a Tabacik, V., Pellegrin, V., Elguero, J., Jacquier, R., Marzin, C., (1971) J. Mol. Struct., 8, p. 173 | ||
| 504 | |a Elguero, J., Marzin, C., Berthou, J., (1973) Bull. Soc. Chim. Fr., p. 3303 | ||
| 504 | |a Sanz, D., Ponce, M.A., Claramunt, R.M., Fernández-Castaño, C., Foces-Foces, C., Elguero, J., (1999) J. Phys. Org. Chem., 12, p. 455 | ||
| 504 | |a Marcos, M., Meléndez, E., Serrano, J.L., Elguero, J., Phan Tan Luu, R., Mathieu, D., (1983) An. Quim., 79 B, p. 664 | ||
| 504 | |a Marcos, M., Meléndez, E., Serrano, J.L., Mathieu, D., Phan Tan Luu, R., Elguero, J., (1983) Bull. Soc. Chim. Belg., 92, p. 429 | ||
| 504 | |a Serrano, J.L., Marcos, M., Meléndez, E., Albano, C., Wold, S., Elguero, J., (1985) Acta Chem. Scand., 39 B, p. 329 | ||
| 504 | |a Elguero, J., Jaime, C., Marcos, M., Meléndez, E., Sánchez-Ferrando, F., Serrano, J.L., (1987) J. Mol. Struct. (THEOCHEM), 150, p. 1 | ||
| 504 | |a Blanco, F., Alkorta, I., Elguero, J., (2007) J. Mol. Struct. (THEOCHEM), 847, p. 25 | ||
| 504 | |a Alkorta, I., Blanco, F., Elguero, J., (2008) Arkivoc, 7, p. 48 | ||
| 504 | |a Silva, A.M.S., Sousa, R.M.S., Jimeno, M.L., Blanco, F., Alkorta, I., Elguero, J., (2008) Magn. Reson. Chem., 46, p. 859 | ||
| 504 | |a Blanco, F., Alkorta, I., Elguero, J., (2009) Croat. Chem. Acta, 82, p. 173 | ||
| 504 | |a Allen, S.C., Steckl, A.J., (2008) Appl. Phys. Lett., 92. , 143309 | ||
| 504 | |a MacDonald, J.H., Mahon, A.R., Allers, L.A., Hassard, J.F., Mainwood, A., Ott, R.J., (1997) Nucl. Instr. Methods Phys. Res. A, 392, p. 227 | ||
| 504 | |a Morrissey, P.F., McCandliss, S.R., Feldman, P.D., Friedman, S.D., (1994) Appl. Opt., 33, p. 2534 | ||
| 504 | |a McIntosh, K.R., Lau, G., Cotsell, J.N., Hanton, K., Bätzner, D.L., Bettiol, F., Richards, B.S., (2009) Prog. Photovolt: Res. Appl., 17, p. 191 | ||
| 504 | |a Janesick, J., (2001) Scientific Charge Coupled Devices, , SPIE, Bellingham, WA, USA | ||
| 504 | |a Allen, F.H., (2002) Acta Crystallogr. Sect. B, 58, p. 380. , (a) Cambridge Structural Database | ||
| 504 | |a Allen, F.H., Motherwell, W.D.S., (2002) Acta Crystallogr. Sect. B, 58, p. 407. , http://www.ccdc.cam.ac.uk, (b), (c) CSD version 5.32, updated Feb. 2011 | ||
| 504 | |a Görner, H., Khanra, S., Weyhermüller, T., Chaudhuri, P., (2006) J. Phys. Chem. A, 110, p. 2587 | ||
| 504 | |a Tang, W., Xiang, Y., Tong, A., (2009) J. Org. Chem., 74, p. 2163 | ||
| 504 | |a Chen, X., Wei, R., Xiang, X., Zhou, Z., Li, K., Song, P., Tong, A., (2011) J. Phys. Chem. C, 115. , 14353 | ||
| 504 | |a Grzegorzek, J., Mielke, Z., Filarowski, A., (2010) J. Mol. Struct., 976, p. 371 | ||
| 504 | |a Oki, M., (1985) Applications of Dynamic NMR Spectroscopy to Organic Chemistry, pp. 364-365. , VCH Publishers, Deerfield Beach, USA | ||
| 504 | |a Liu, S.-I., (2009) J. Comput. Chem., 30, p. 2176 | ||
| 504 | |a Hökelek, T., Bílge, S., Kilic, Z., (2006) Anal. Sci., 22, pp. x115 | ||
| 504 | |a Berger, S., Braun, S., (2004) 200 and More NMR Experiments, , Wiley-VCH, Weinheim | ||
| 504 | |a Parr, R.G., Yang, W., (1989) Density-Functional Theory of Atoms and Molecules, , Oxford Science Publications: Oxford, New York | ||
| 504 | |a Bartolotti, L.J., Fluchick, K., (1996) Reviews in Computational Chemistry, 7, p. 187. , (eds: K. B. Lipkowitz, D. B. Boyd), VCH Publishers, NewYork, p | ||
| 504 | |a Frisch, M.J., Pople, J.A., Krishnam, R., Binkley, J.S., (1984) J. Chem. Phys., 80, p. 3265 | ||
| 504 | |a Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., (2009) Gaussian 09, Revision A.1, , Gaussian, Inc., Wallingford CT | ||
| 504 | |a McIver, J.W., Komornicki, A.K., (1972) J. Am. Chem. Soc., 94, p. 2625 | ||
| 504 | |a Ditchfield, R., (1974) Mol. Phys., 27, p. 789 | ||
| 504 | |a London, F., (1937) J. Phys. Radium, 8, p. 397 | ||
| 504 | |a Tomasi, J., Mennucci, B., Cammi, R., (2005) Chem. Rev., 105, p. 2999 | ||
| 504 | |a Blanco, F., Alkorta, I., Elguero, J., (2007) Magn. Reson. Chem., 45, p. 797 | ||
| 504 | |a Pinto, J., Silva, V.L.M., Silva, A.M.S., Claramunt, R.M., Sanz, D., Torralba, M.C., Torres, M.R., Elguero, J., (2013) Magn. Reson. Chem., 51, p. 203 | ||
| 504 | |a Giannozzi, P., Baroni, S., Bonini, N., Calandra, M., Car, R., Cavazzoni, C., Ceresoli, D., Wentzcovitch, R.M., (2009) J. Phys. Condens. Matter, 21, pp. 395502-395519. , www-quantum-espresso.org | ||
| 504 | |a Grimme, S., (2004) J. Comput. Chem., 25, pp. 1463-1473 | ||
| 504 | |a Grimme, S., (2006) J. Comput. Chem., 27, pp. 1787-1799 | ||
| 504 | |a Grimme, S., Antony, J., Ehrlich, S., Krieg, H., (2010) J. Chem. Phys., 132. , 154104-154123 | ||
| 504 | |a Perdew, J.P., Burke, K., Ernzerhof, M., (1996) Phys. Rev. Lett., 77, pp. 3865-3868 | ||
| 504 | |a Perdew, J.P., Burke, K., Wang, Y., (1996) Phys. Rev. B, 54. , 16533-16539 | ||
| 504 | |a Bertolasi, V., Gilli, P., Ferretti, V., Gilli, G., Vaughan, K., (1999) New J. Chem., 23, p. 1261 | ||
| 504 | |a Olivieri, A.C., Wilson, R.B., Paul, I.C., Curtin, D.Y., (1989) J. Am. Chem. Soc., 111, p. 5525 | ||
| 504 | |a Alarcõn, S.H., Olivieri, A.C., González-Sierra, M., (1994) J. Chem. Soc. Perkin Trans., 2, p. 1067 | ||
| 504 | |a Katritzky, A.R., Ghiviriga, I., Leeming, P., Soti, F., (1996) Magn. Reson. Chem., 34, p. 518 | ||
| 504 | |a Jaworska, M., Hrynczyszyn, P.B., Welniak, M., Wojtzcak, A., Nowicka, K., Krasinski, G., Ciesielski, W., Potrzebowski, M.J., (2010) J. Phys. Chem. A, 114. , 12522 | ||
| 504 | |a Rozwadowski, Z., Majewski, E., Dziembowska, T., Hansen, P.E., (1999) J. Chem. Soc. Perkin Trans., 2, p. 2809 | ||
| 504 | |a Racané, L., Mihalic, Z., Ceric, H., Popovic, J., Tralic-Kulenovic, V., (2013) Dyes Pigm., 96, p. 672 | ||
| 504 | |a Alarcõn, S.H., Olivieri, A.C., Sanz, D., Claramunt, R.M., Elguero, J., (2004) J. Mol. Struct., 705, p. 1 | ||
| 504 | |a Alarcõn, S.H., Olivieri, A.C., Jonsen, P., (1993) J. Chem. Soc. Perkin Trans., 2, p. 1783 | ||
| 504 | |a Joshi, H., Kamounah, F.S., Zwan, G.V.D., Gooijer, C., Antonov, L., (2001) J. Chem. Soc. Perkin Trans., 2, p. 2303 | ||
| 504 | |a Fabian, W.M.F., Antonov, L., Nedeltcheva, D., Kamounah, F.S., Taylor, P.J., (2004) J. Phys. Chem. A, 108, p. 7603 | ||
| 504 | |a Sharif, S., Denisov, G.S., Toney, M.D., Limbach, H.H., (2006) J. Am. Chem. Soc., 128, p. 3375 | ||
| 504 | |a Golubev, N.S., Smirnov, S.N., Tolstoy, P.M., Sharif, S., Toney, M.D., Denisov, G.S., Limbach, H.H., (2007) J. Mol. Struct., 844-845, p. 319 | ||
| 504 | |a Elguero, J., Marzin, C., Katritzky, A.R., Linda, P., (1976) The Tautomerism of Heterocycles, p. 29. , Academic Press, New York | ||
| 504 | |a Lee, H.Y., Song, X., Park, H., Baik, M.-H., Lee, D., (2010) J. Am. Chem. Soc., 132. , 12133 | ||
| 504 | |a Özen, A.S., Doruker, P., Aviyente, V., (2007) J. Phys. Chem. A, 111. , 13506 | ||
| 504 | |a Golcu, A., Tumer, M., Demirelli, H., Wheatley, R.A., (2005) Inorg. Chim. Acta, 358, p. 1785 | ||
| 504 | |a Galic, N., Cimerman, Z., Tomisic, V., (2008) Spectrochim. Acta A, 71, p. 1274 | ||
| 504 | |a Ruiz-Molina, D., Veciana, J., Wurst, K., Hendrickson, D.N., Rovira, C., (2000) Inorg. Chem., 39, p. 617 | ||
| 504 | |a You, W., Zhu, H.-Y., Huang, W., Hu, B., Fan, Y., You, X.-Z., (2010) Dalton Trans., 39, p. 7876 | ||
| 504 | |a Fita, P., Luzina, E., Dziembowska, T., Kopec, D., Piatkowski, P., Radzewicz, C., Grabowska, A., (2005) Chem. Phys. Lett., 416, p. 305 | ||
| 504 | |a Ziõlek, M., Kubicki, J., MacIejewski, A., Naskrecki, P., Grabowska, A., (2006) J. Chem. Phys., 124. , 124518 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a 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. |l eng | |
| 593 | |a Chemistry Department and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal | ||
| 593 | |a 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 | ||
| 593 | |a Departamento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires and IFIBA, 1428 Buenos Aires, Argentina | ||
| 593 | |a Instituto de Química Médica, Centro de Química Orgánica Manuel Lora-Tamayo, IQM-CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain | ||
| 690 | 1 | 0 | |a CPMAS |
| 690 | 1 | 0 | |a DFT-D CALCULATIONS |
| 690 | 1 | 0 | |a LUMOGEN |
| 690 | 1 | 0 | |a NMR |
| 690 | 1 | 0 | |a SALICYLALDAZINE |
| 690 | 1 | 0 | |a TEMPERATURE EFFECTS |
| 690 | 1 | 0 | |a DRUG DERIVATIVE |
| 690 | 1 | 0 | |a HYDRAZINE DERIVATIVE |
| 690 | 1 | 0 | |a NAPHTHOL DERIVATIVE |
| 690 | 1 | 0 | |a THIORIDAZINE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a CPMAS |
| 690 | 1 | 0 | |a DFT-D CALCULATIONS |
| 690 | 1 | 0 | |a LUMOGEN |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a QUANTUM THEORY |
| 690 | 1 | 0 | |a SALICYLALDAZINE |
| 690 | 1 | 0 | |a SOLUTION AND SOLUBILITY |
| 690 | 1 | 0 | |a TEMPERATURE EFFECTS |
| 690 | 1 | 0 | |a X RAY CRYSTALLOGRAPHY |
| 690 | 1 | 0 | |a CPMAS |
| 690 | 1 | 0 | |a DFT-D CALCULATIONS |
| 690 | 1 | 0 | |a LUMOGEN |
| 690 | 1 | 0 | |a NMR |
| 690 | 1 | 0 | |a SALICYLALDAZINE |
| 690 | 1 | 0 | |a TEMPERATURE EFFECTS |
| 690 | 1 | 0 | |a CRYSTALLOGRAPHY, X-RAY |
| 690 | 1 | 0 | |a HYDRAZINES |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MODELS, MOLECULAR |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a NAPHTHOLS |
| 690 | 1 | 0 | |a QUANTUM THEORY |
| 690 | 1 | 0 | |a SOLUTIONS |
| 690 | 1 | 0 | |a THIORIDAZINE |
| 700 | 1 | |a Silva, V.L.M. | |
| 700 | 1 | |a Claramunt, R.M. | |
| 700 | 1 | |a María, D.S. | |
| 700 | 1 | |a Ferraro, Marta Beatriz | |
| 700 | 1 | |a Reviriego, F. | |
| 700 | 1 | |a Alkorta, I. | |
| 700 | 1 | |a Elguero, J. | |
| 773 | 0 | |d 2013 |g v. 51 |h pp. 530-540 |k n. 9 |p Magn. Reson. Chem. |x 07491581 |w (AR-BaUEN)CENRE-972 |t Magnetic Resonance in Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1002/mrc.3983 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_07491581_v51_n9_p530_Silva |y Handle |
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