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, UVeVis, <sup>1</sup>H and <sup>13</sup>C NMR spectrosc...
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| Autores principales: | , , , , , , |
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| Formato: | Articulo |
| Lenguaje: | Inglés |
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2017
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| Acceso en línea: | http://sedici.unlp.edu.ar/handle/10915/108943 https://www.sciencedirect.com/science/article/abs/pii/S0022286016312571 |
| Aporte de: |
| id |
I19-R120-10915-108943 |
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dspace |
| institution |
Universidad Nacional de La Plata |
| institution_str |
I-19 |
| repository_str |
R-120 |
| collection |
SEDICI (UNLP) |
| language |
Inglés |
| topic |
Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties |
| spellingShingle |
Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties Rocha, Mariana Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
| topic_facet |
Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties |
| 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, UVeVis, <sup>1</sup>H and <sup>13</sup>C 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)–H interaction between the lone pair located in the N-atom of the azomethine group and the C–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. |
| format |
Articulo Articulo |
| author |
Rocha, Mariana Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. |
| author_facet |
Rocha, Mariana Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. |
| author_sort |
Rocha, Mariana |
| 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 |
| publishDate |
2017 |
| url |
http://sedici.unlp.edu.ar/handle/10915/108943 https://www.sciencedirect.com/science/article/abs/pii/S0022286016312571 |
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