Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation
- Autores
- Rocha, Mariana; Di Santo, A.; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Cukiernik, F. D.; Ulic, Sonia Elizabeth; Gil, Diego M.
- Año de publicación
- 2017
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- 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, 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)–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.
Facultad de Ciencias Exactas
Centro de Química Inorgánica
Instituto de Física La Plata - Materia
-
Ciencias Exactas
Química
Física
Schiff bases
crystal structure
quantum chemical calculations
IR and Raman spectroscopy
Hirshfeld surface analysis
mesomorphic properties - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- http://creativecommons.org/licenses/by-nc-sa/4.0/
- Repositorio
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/108943
Ver los metadatos del registro completo
id |
SEDICI_027706c6c8c7593e7adbf4b168d55e61 |
---|---|
oai_identifier_str |
oai:sedici.unlp.edu.ar:10915/108943 |
network_acronym_str |
SEDICI |
repository_id_str |
1329 |
network_name_str |
SEDICI (UNLP) |
spelling |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigationRocha, MarianaDi Santo, A.Echeverría, Gustavo AlbertoPiro, Oscar EnriqueCukiernik, F. D.Ulic, Sonia ElizabethGil, Diego M.Ciencias ExactasQuímicaFísicaSchiff basescrystal structurequantum chemical calculationsIR and Raman spectroscopyHirshfeld surface analysismesomorphic propertiesThe 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.Facultad de Ciencias ExactasCentro de Química InorgánicaInstituto de Física La Plata2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf24-36http://sedici.unlp.edu.ar/handle/10915/108943enginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286016312571info:eu-repo/semantics/altIdentifier/issn/0022-2860info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2016.11.071info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:24:41Zoai:sedici.unlp.edu.ar:10915/108943Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:24:42.138SEDICI (UNLP) - Universidad Nacional de La Platafalse |
dc.title.none.fl_str_mv |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
title |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation |
spellingShingle |
Supramolecular self-assembly of a new multi-conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation Rocha, Mariana Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties |
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 |
dc.creator.none.fl_str_mv |
Rocha, Mariana Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. |
author |
Rocha, Mariana |
author_facet |
Rocha, Mariana Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. |
author_role |
author |
author2 |
Di Santo, A. Echeverría, Gustavo Alberto Piro, Oscar Enrique Cukiernik, F. D. Ulic, Sonia Elizabeth Gil, Diego M. |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties |
topic |
Ciencias Exactas Química Física Schiff bases crystal structure quantum chemical calculations IR and Raman spectroscopy Hirshfeld surface analysis mesomorphic properties |
dc.description.none.fl_txt_mv |
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. Facultad de Ciencias Exactas Centro de Química Inorgánica Instituto de Física La Plata |
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. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Articulo http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://sedici.unlp.edu.ar/handle/10915/108943 |
url |
http://sedici.unlp.edu.ar/handle/10915/108943 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286016312571 info:eu-repo/semantics/altIdentifier/issn/0022-2860 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2016.11.071 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) |
dc.format.none.fl_str_mv |
application/pdf 24-36 |
dc.source.none.fl_str_mv |
reponame:SEDICI (UNLP) instname:Universidad Nacional de La Plata instacron:UNLP |
reponame_str |
SEDICI (UNLP) |
collection |
SEDICI (UNLP) |
instname_str |
Universidad Nacional de La Plata |
instacron_str |
UNLP |
institution |
UNLP |
repository.name.fl_str_mv |
SEDICI (UNLP) - Universidad Nacional de La Plata |
repository.mail.fl_str_mv |
alira@sedici.unlp.edu.ar |
_version_ |
1844616123974156288 |
score |
13.070432 |