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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todo:paper_00222860_v1133_n_p24_Rocha2023-10-03T14:30:32Z Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation Rocha, M. Di Santo, A. Echeverría, G.A. Piro, O.E. Cukiernik, F.D. Ulic, S.E. Gil, D.M. Crystal structure Hirshfeld surface analysis IR and Raman spectroscopy Mesomorphic properties Quantum chemical calculations Schiff bases Chemical analysis Chemical bonds Differential scanning calorimetry Geometry Hydrogen bonds Nuclear magnetic resonance spectroscopy Quantum chemistry Self assembly Single crystals Surface analysis X ray diffraction Hirshfeld surfaces IR and Raman spectroscopy Mesomorphic property Quantum chemical calculations Schiff basis Crystal structure 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. Fil:Cukiernik, F.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00222860_v1133_n_p24_Rocha |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Crystal structure Hirshfeld surface analysis IR and Raman spectroscopy Mesomorphic properties Quantum chemical calculations Schiff bases Chemical analysis Chemical bonds Differential scanning calorimetry Geometry Hydrogen bonds Nuclear magnetic resonance spectroscopy Quantum chemistry Self assembly Single crystals Surface analysis X ray diffraction Hirshfeld surfaces IR and Raman spectroscopy Mesomorphic property Quantum chemical calculations Schiff basis Crystal structure |
| spellingShingle |
Crystal structure Hirshfeld surface analysis IR and Raman spectroscopy Mesomorphic properties Quantum chemical calculations Schiff bases Chemical analysis Chemical bonds Differential scanning calorimetry Geometry Hydrogen bonds Nuclear magnetic resonance spectroscopy Quantum chemistry Self assembly Single crystals Surface analysis X ray diffraction Hirshfeld surfaces IR and Raman spectroscopy Mesomorphic property Quantum chemical calculations Schiff basis Crystal structure Rocha, M. Di Santo, A. Echeverría, G.A. Piro, O.E. Cukiernik, F.D. Ulic, S.E. Gil, D.M. Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| topic_facet |
Crystal structure Hirshfeld surface analysis IR and Raman spectroscopy Mesomorphic properties Quantum chemical calculations Schiff bases Chemical analysis Chemical bonds Differential scanning calorimetry Geometry Hydrogen bonds Nuclear magnetic resonance spectroscopy Quantum chemistry Self assembly Single crystals Surface analysis X ray diffraction Hirshfeld surfaces IR and Raman spectroscopy Mesomorphic property Quantum chemical calculations Schiff basis Crystal structure |
| description |
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. |
| format |
JOUR |
| author |
Rocha, M. Di Santo, A. Echeverría, G.A. Piro, O.E. Cukiernik, F.D. Ulic, S.E. Gil, D.M. |
| author_facet |
Rocha, M. Di Santo, A. Echeverría, G.A. Piro, O.E. Cukiernik, F.D. Ulic, S.E. Gil, D.M. |
| author_sort |
Rocha, M. |
| title |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| title_short |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| title_full |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| title_fullStr |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| title_full_unstemmed |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| title_sort |
supramolecular self-assembly of a new multi-conformational schiff base through hydrogen bonds: crystal structure, spectroscopic and theoretical investigation |
| url |
http://hdl.handle.net/20.500.12110/paper_00222860_v1133_n_p24_Rocha |
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