Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation
The compound 4-(4-dimethylaminobenzylidene)aminoacetophenone was synthesized by condensation of 4-aminoacetophenone and 4-(dimethylamino) benzaldehyde in ethanol. This compound was characterized by CG-MS, infrared, Raman, UV–Vis, 1H and 13C NMR spectroscopy. The crystal structure was solved by singl...
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Elsevier B.V.
2017
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| LEADER | 17191caa a22013577a 4500 | ||
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| 003 | AR-BaUEN | ||
| 005 | 20250820094201.0 | ||
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| 024 | 7 | |2 scopus |a 2-s2.0-85003604062 | |
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| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Rocha, M. | |
| 245 | 1 | 0 | |a Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| 260 | |b Elsevier B.V. |c 2017 | ||
| 270 | 1 | 0 | |m Gil, D.M.; INQUINOA (CONICET-UNT), Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, San Lorenzo 456, Argentina; email: dmgil@fbqf.unt.edu.ar |
| 504 | |a Schiff, H., Schiff, H., Mitteilungen aus dem universitatslaboratorium in Pisa: eineneue reihe organischer basen (1864) Justus Liebigs Ann. Chem., 131, p. 118 | ||
| 504 | |a Dhar, D.N., Taploo, C.L., Schiff bases and their applications (1982) J. Sci. Ind. Res., 41, p. 501 | ||
| 504 | |a Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B., Bartl, F., Biological properties of schiff bases and azo derivatives of phenols (2009) Curr. Org. Chem., 13, p. 124 | ||
| 504 | |a Bringmann, G., Dreyer, M., Faber, J.H., Dalsgaard, P.W., Staerk, D., Jaroszewski, J.W., Ancistrotanzanine C and related 5,1′- and 7,3′-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis (2004) J. Nat. Prod., 67, p. 743 | ||
| 504 | |a Salimon, J., Salih, N., Ibraheem, H., Yousief, E., Synthesis of 2-N-salicylidene-5-(substituted)-1,3,4-thiadiazole as potential antimicrobial agents (2010) Asian J. Chem., 22, p. 5289 | ||
| 504 | |a Guo, Z., Xing, R., Liu, S., Zhong, Z., Ji, X., Wang, L., Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan (2007) Carbohydr. Res., 342, p. 1329 | ||
| 504 | |a Danaee, I., Ghasemi, O., Rashed, G.R., Rashvand Avei, M., Maddahy, M.H., Effect of hydroxyl group position on adsorption behavior and corrosion inhibition of hydroxybenzaldehyde Schiff bases: electrochemical and quantum calculations Original Research Article (2013) J. Mol. Struct., 1035, p. 247 | ||
| 504 | |a Drozdzak, R., Allaert, B., Ledoux, N., Dragutan, I., Verport, R., Ruthenium complexes bearing bidentate Schiff-base ligands as efficient catalysts for organic and polymer synthesis (2005) Coord. Chem. Rev., 249, p. 3055 | ||
| 504 | |a Zeyrek, C.T., Elmali, A., Elerman, Y., Synthesis and crystal structures of a new μ-Bis(tetradentate) schiff base ligand and its mononuclear iron(III) complex: iron(III) induced imidazolidine ring hydrolysis of binucleating schiff base ligand (2005) Z. Naturforsch, 60b, p. 520 | ||
| 504 | |a Taggi, A.E., Hafez, A.M., Wack, H., Young, B., Ferraris, D., Lectka, T., The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of β-lactams (2002) J. Am. Chem. Soc., 124, p. 6626 | ||
| 504 | |a Ramnauth, R., Al-Juaid, S., Motevalli, M., Parkin, B.C., Sullivan, A.C., Synthesis, structure, and catalytic oxidation chemistry from the first Oxo−Imido schiff base metal complexes (2004) Inorg. Chem., 43, p. 4072 | ||
| 504 | |a Mishra, A.P., Gupta, P., Effect of chelation on therapeutic potential of drugs: synthesis, structure, antimicrobial and insecticidal activity of 3d-metal complexes involving Schiff-bases (2011) J. Chem. Pharm. Res., 3, p. 150 | ||
| 504 | |a Anis, I., Aslam, M., Noreen, Z., Afza, N., Hussain, A., chaudhry, A.H., safder, M., A review (part B) – use of schiff base transition metal complexes as a catalyst (2013) Int. J. Curr. Pharm. Res., 5, p. 30 | ||
| 504 | |a Alexander, S., Udayakumar, V., Gayathri, V., Hydrogenation of olefins by polymer-bound palladium(II) Schiff base catalyst (2009) J. Mol. Catal. A – Chem., 314, p. 21 | ||
| 504 | |a Pu, S., Tong, Z., Liu, G., Wang, R., Multi-addressable molecular switches based on a new diarylethene salicylal Schiff base derivative (2013) J. Mater. Chem. C, 1, p. 4726 | ||
| 504 | |a Ali, O.A.M., Abdel-Rahman, L.H., Ramadan, R.M., Ruthenium carbonyl derivatives of N-salicylidene-2-hydroxyaniline Schiff base (2007) J. Coord. Chem., 60, p. 2335 | ||
| 504 | |a Khan, M.I., Khan, A., Hussain, I., Khan, M.A., Gul, S., Iqbal, M., Ur-Rahman, I., Khuda, F., Spectral, XRD, SEM and biological properties of new mononuclear Schiff base transition metal complexes (2013) Inorg. Chem. Commun., 35, p. 104 | ||
| 504 | |a Leela, S., Hema, R., Stoeckli-Evans, H., Ramamurthi, K., Bhagavannarayana, G., Design, synthesis, growth and characterization of 4-methoxy-4′-dimethylamino-benzylidene aniline (MDMABA): a novel third order nonlinear optical material (2010) Spectrochim. Acta A, 77, p. 927 | ||
| 504 | |a Zeyrek, C.T., Alpaslam, G., Alyar, H., Yildiz, M., Dilek, N., Ünver, H., Synthesis, molecular structure, spectroscopic and theoretical studies on E-2-ethoxy-4-[(4-ethoxyphenylimino) methyl] pheno (2015) J. Mol. Struct., 1088, p. 14 | ||
| 504 | |a Leela, S., Ramamurthi, K., Bhagavannarayana, G., Synthesis, growth, spectral, thermal, mechanical and optical properties of 4-chloro-4′dimethylamino-benzylidene aniline crystal: a third order nonlinear optical material (2009) Spectrochim. Acta A, 74, p. 78 | ||
| 504 | |a Subashini, A., Kumaravel, R., Leela, S., Evans, H.S., Sastikumar, D., Ramamurthi, K., Synthesis, growth and characterization of 4-bromo-4′chloro benzylidene aniline—a third order non linear optical material (2011) Spectrochim. Acta A, 78, p. 935 | ||
| 504 | |a Pathak, S., Kumar, A., Tandon, P., Molecular structure and vibrational spectroscopic investigation of 4-chloro-4′dimethylamino-benzylidene aniline using density functional theory (2010) J. Mol. Struct., 981, p. 1 | ||
| 504 | |a Fang, Z., Wu, F., Yi, B., Cao, C., Xie, X., Effects of molecular conformation on the spectroscopic properties of 4,4′-disubstituted benzylideneanilines (2016) J. Mol. Struct., 1104, p. 52 | ||
| 504 | |a Collings, P.J., Hird, M., Introduction to Liquid Crystals: Chemistry and Physics (1998), Taylor & Francis Ltd. U.K; Demus, D., Goodby, J., Gray, G.W., Spiess, H.W., Vill, V., Handbook of Liquid Crystals (1998), Wiley- VCH Weinheim; Donio, B., Guillon, D., Deschenaux, R., Bruce, D.W., McCleverty, J., Meyer, T.J., Comprehensive Coordination Chemistry (2004), Elsevier Pergamon Amsterdam; Ha, S.T., Ong, L.K., Wong, J.P., Yeap, G.Y., Lin, H.C., Ong, S.T., Koh, T.M., Mesogenic Schiff's base ether with dimethylamino end group (2009) Phase Transitions, 82, p. 387 | ||
| 504 | |a Ha, S.T., Ong, L.K., Ong, S.T., Yeap, G.Y., Wong, J.P.W., Koh, T.M., Lin, H.C., Synthesis and mesomorphic properties of new Schiff base esters with different alkyl chains (2009) Chin. Chem. Lett., 20, p. 767 | ||
| 504 | |a CrysAlisPro, Oxford Diffraction Ltd., version 1.171.33.48 (release 15-09-2009 CrysAlis171.NET); Sheldrick, G.M., A short history of SHELX (2008) Acta Crystallogr. A, 64, p. 112 | ||
| 504 | |a Sheldrick, G.M., Crystal structure refinement with SHELX (2015) Acta Cryst. A, 71, p. 3 | ||
| 504 | |a Frisch, M.J., Pople, J.A., 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., Montgomery, J.A., Jr., Pople, J.A., Gaussian 03, Revision C.02 (2004), Gaussian, Inc. Wallingford, CT; Becke, A.D., Density-functional thermochemistry. III. The role of exact exchange (1993) J. Chem. Phys., 98, p. 5648 | ||
| 504 | |a Lee, C., Yang, W., Parr, R.G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density (1988) Phys. Rev. B, 37, p. 785 | ||
| 504 | |a Jamróz, M.H., Vibrational energy distribution analysis (VEDA): scopes and limitations (2013) Spectrochim. Acta A, 114, p. 220 | ||
| 504 | |a Jamróz, M.H., Vibrational Energy Distribution Analysis VEDA4, Warsaw (2004); Elliot, P., Furche, F., Burke, K., (2009) Rev. Comp. Chem., 26, p. 91 | ||
| 504 | |a Cheeseman, J.R., Trucks, G.W., Keith, T.A., Frisch, M.J., A comparison of models for calculating nuclear magnetic resonance shielding tensors (1996) Chem. Phys., 104, p. 5497 | ||
| 504 | |a Wolf, S.K., Grimwood, D.J., McKinnon, J.J., Turner, M.J., Jayatilaka, D., Spackman, M.A., CrystalExplorer (Version 3.1) (2012), University of Western Austalia; Spackman, M.A., Jayatilaka, D., Hirshfeld surface analysis (2009) CrystEngComm, 11, p. 19 | ||
| 504 | |a Spackman, M.A., McKinnon, J.J., Fingerprinting intermolecular interactions in molecular crystals (2002) CrystEngComm, 4, p. 378 | ||
| 504 | |a Spackman, M.A., Molecules in crystals (2013) Phys. Scr., 87, p. 048103 | ||
| 504 | |a Yathirajan, H.S., Vijesh, A.M., Narayana, B., Sarojini, B.K., Bolte, M., 1-(4-{[(E)-(4-Diethylamino)-2-hydroxyphenyl)-methylene]amino}phenyl)ethanone (2007) Acta Cryst., E63. , o936 | ||
| 504 | |a Rocha, M., Di Santo, A., Arias, J.M., Gil, D.M., Ben Altabef, A., Ab-initio and DFT calculations on molecular structure, NBO, HOMO–LUMO study and a new vibrational analysis of 4-(Dimethylamino) Benzaldehyde (2015) Spectrochim. Acta A, 136, p. 635 | ||
| 504 | |a Lizarrága, E., Gil, D.M., Echeverría, G.A., Piro, O.E., Catalán, C.A.N., Ben Altabef, A., Synthesis, crystal structure, conformational and vibrational properties of 6-acetyl-2,2-dimethyl-chromane (2014) Spectrochim. Acta A, 127, p. 74 | ||
| 504 | |a Toy, M., Tanak, H., Molecular structure and vibrational and chemical shift assignments of 3′-chloro-4-dimethylamino azobenzene by DFT calculations (2016) Spectrochim. Acta A, 152, p. 530 | ||
| 504 | |a Ramadan, R.M., Al-Nasr, K.A., Noureldeen, A.F.H., Synthesis, spectroscopic studies, antimicrobial activities and antitumor of a new monodentate V-shaped Schiff base and its transition metal complexes (2014) Spectrochim. Acta A, 132, p. 417 | ||
| 504 | |a Khan, M.I., Khan, A., Hussain, I., Khan, M.A., Gul, S., Iqbal, M., Rahman, I.U., Khuda, F., Spectral, XRD, SEM and biological properties of new mononuclear Schiff base transition metal complexes (2013) Inorg. Chem. Commun., 35, p. 104 | ||
| 504 | |a Subramanian, M.K., Anbarasan, P.M., Ilangovan, V., Moorthy Babu, S., FT-IR, NIR-FT-Raman and gas phase infrared spectra of 3-aminoacetophenone by density functional theory and ab initio Hartree–Fock calculations (2008) Spectrochim. Acta A, 71, p. 59 | ||
| 504 | |a Pathak, S., Kumar, A., Tandon, P., Molecular structure and vibrational spectroscopic investigation of 4-chloro-4′dimethylamino-benzylidene aniline using density functional theory (2010) J. Mol. Struct., 981, p. 1 | ||
| 504 | |a Arjunan, V., Kalaivani, M., Senthilkumari, S., Mohan, S., Vibrational, NMR and quantum chemical investigations of acetoacetanilde, 2-chloroacetoacetanilide and 2-methylacetoacetanilide (2013) Spectrochim. Acta A, 115, p. 154 | ||
| 504 | |a Leela, S., Hema, R., Stoeckli-Evans, H., Ramamurthi, K., Bhagavannarayana, G., Design, synthesis, growth and characterization of 4-methoxy-4′-dimethylamino-benzylidene aniline (MDMABA): a novel third order nonlinear optical material (2010) Spectrochim. Acta A, 77, p. 927 | ||
| 504 | |a Kutulya, L.A., Morina, Shevchenko, V.F., Krasovitskll, B.M., Spectroluminescent properties of azomethine derivatives of 1-(4-formylphenyl)-3-aryl-5-phenyl-2-pyrazolines (1979) J. Appl. Spectrosc., 31, p. 1491 | ||
| 504 | |a Dierking, I., Textures of Liquid Crystals (2003), Wiley-VCH Weinheim; www.lci-publisher.com/, LiqCryst5.1.43, V. Vill, G. Peters, S. Thiemann (Eds.), LCI Publisher GmbH; Demus, D., One hundred years of liquid-crystal chemistry: thermotropic liquid crystals with conventional and unconventional molecular structure (1989) Liq. Cryst., 5, p. 75 | ||
| 504 | |a Castellano, J.A., Goldmacher, J.E., Barton, L.A., Kane, J.S., Liquid crystals.II. Effects of terminal group substitution on the mesomorphic behavior of some benzylideneanilines (1968) J. Org. Chem., 33, p. 3501 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a The compound 4-(4-dimethylaminobenzylidene)aminoacetophenone was synthesized by condensation of 4-aminoacetophenone and 4-(dimethylamino) benzaldehyde in ethanol. This compound was characterized by CG-MS, infrared, Raman, UV–Vis, 1H and 13C NMR spectroscopy. The crystal structure was solved by single-crystal X-ray diffraction methods. The crystallographic data reveals that there are four independent molecules per asymmetric unit, that mainly differ from one another in rotations around the σ-bond of the azomethine N-atom with the phenyl ring. A detailed analysis of the intermolecular interactions in the four conformers of the compound has been performed using Hirshfeld surfaces and their associated two-dimensional fingerprint plots. The optimized geometrical parameters and calculated spectroscopic features obtained by quantum chemical calculations at B3LYP method show a very good agreement with the experimental data. Moreover, Natural Bond Orbital (NBO) analysis confirms the strong hyper-conjugative LP N(n1)→ σ* C(n9)[sbnd]H interaction between the lone pair located in the N-atom of the azomethine group and the C[sbnd]H bond. Liquid crystalline properties of the Schiff base were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and Powder X-ray diffraction techniques. Mesomorphic behaviour was observed in this unsymmetrical azomethine. Based on POM and DSC measurements, the hexatic Smetic B phase was detected. © 2016 Elsevier B.V. |l eng | |
| 536 | |a Detalles de la financiación: Deutscher Akademischer Austauschdienst | ||
| 536 | |a Detalles de la financiación: D542/2 | ||
| 536 | |a Detalles de la financiación: Universidad Nacional de La Plata, UNLP, 14/B152, 11X/683 | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT-2013-0697, PME06 2804, PICT06 2315 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 1529, PIP 0359, PIP 0205 | ||
| 536 | |a Detalles de la financiación: This work was supported by CONICET ( PIP 1529 , PIP 0205 , and PIP 0359 ), ANPCyT ( PME06 2804 , PICT06 2315 , and PICT-2013-0697 ), CIUNT (Project D542/2 ), UNLP (Project 11X/683 ), and UNLu of Argentina (Project 14/B152 ). SEU thanks Deutscher Akademischer Austauschdienst Germany (DAAD) for an equipment grant and financial support. M.R. and A.D.S. thank CONICET for doctoral fellowships. Appendix A | ||
| 593 | |a INQUINOA (CONICET-UNT), Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, San Lorenzo 456, Tucumán, T4000CAN, Argentina | ||
| 593 | |a Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP, CONICET, CCT- La Plata, C.C. 67, La Plata, 1900, Argentina | ||
| 593 | |a DQIAQF/INQUIMAE, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, Núñez, CABA, C1428EHA, Argentina | ||
| 593 | |a CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 and 115, La Plata, 1900, Argentina | ||
| 593 | |a Departamento de Ciencias Básicas, Universidad Nacional de Luján, Rutas 5 y 7, Luján, Buenos Aires 6700, Argentina | ||
| 690 | 1 | 0 | |a CRYSTAL STRUCTURE |
| 690 | 1 | 0 | |a HIRSHFELD SURFACE ANALYSIS |
| 690 | 1 | 0 | |a IR AND RAMAN SPECTROSCOPY |
| 690 | 1 | 0 | |a MESOMORPHIC PROPERTIES |
| 690 | 1 | 0 | |a QUANTUM CHEMICAL CALCULATIONS |
| 690 | 1 | 0 | |a SCHIFF BASES |
| 690 | 1 | 0 | |a CHEMICAL ANALYSIS |
| 690 | 1 | 0 | |a CHEMICAL BONDS |
| 690 | 1 | 0 | |a DIFFERENTIAL SCANNING CALORIMETRY |
| 690 | 1 | 0 | |a GEOMETRY |
| 690 | 1 | 0 | |a HYDROGEN BONDS |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a QUANTUM CHEMISTRY |
| 690 | 1 | 0 | |a SELF ASSEMBLY |
| 690 | 1 | 0 | |a SINGLE CRYSTALS |
| 690 | 1 | 0 | |a SURFACE ANALYSIS |
| 690 | 1 | 0 | |a X RAY DIFFRACTION |
| 690 | 1 | 0 | |a HIRSHFELD SURFACES |
| 690 | 1 | 0 | |a IR AND RAMAN SPECTROSCOPY |
| 690 | 1 | 0 | |a MESOMORPHIC PROPERTY |
| 690 | 1 | 0 | |a QUANTUM CHEMICAL CALCULATIONS |
| 690 | 1 | 0 | |a SCHIFF BASIS |
| 690 | 1 | 0 | |a CRYSTAL STRUCTURE |
| 700 | 1 | |a Di Santo, A. | |
| 700 | 1 | |a Echeverría, G.A. | |
| 700 | 1 | |a Piro, Oscar Enrique | |
| 700 | 1 | |a Cukiernik, F.D. | |
| 700 | 1 | |a Ulic, S.E. | |
| 700 | 1 | |a Gil, D.M. | |
| 773 | 0 | |d Elsevier B.V., 2017 |g v. 1133 |h pp. 24-36 |p J. Mol. Struct. |x 00222860 |w (AR-BaUEN)CENRE-222 |t Journal of Molecular Structure | |
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| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222860_v1133_n_p24_Rocha |y Handle |
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