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dc.contributor.author
Khurshid, Asma
dc.contributor.author
Saeed, Aamer
dc.contributor.author
Shabir, Ghulam
dc.contributor.author
Gil, Diego Mauricio
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dc.contributor.author
Bolte, Michael
dc.contributor.author
Erben, Mauricio Federico
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dc.date.available
2024-02-14T12:47:51Z
dc.date.issued
2023-04
dc.identifier.citation
Khurshid, Asma; Saeed, Aamer; Shabir, Ghulam; Gil, Diego Mauricio; Bolte, Michael; et al.; Synthesis of phenazone based carboxamide under thiourea reaction conditions. Molecular and crystal structure, Hirshfeld surface analysis and intermolecular interaction energies; Elsevier Science; Journal of Molecular Structure; 1278; 4-2023; 1-12
dc.identifier.issn
0022-2860
dc.identifier.uri
http://hdl.handle.net/11336/226780
dc.description.abstract
Considering the added advantage of active pyrazolone pharmacophore and phenazone drug itself with associated medicinal applications, we herein aim to derivatize this potent active non-steroidal anti-inflammatory drug (NSAID) to its thiourea derivative for enhanced biological potential. Thiourea reaction conditions were utilized to make use of active amino group of phenazone drug in reaction with furan-2-carbonyl isothiocyanate for formation of corresponding aroyl thiourea derivative. However, on detailed single crystal XRD, spectroscopic and analytical investigations, it become apparent the formation of phenazone-carbonothioyl carboxamide rearranged product. The novel compound was characterized by spectroscopic methods and its crystal structure was determined by single-crystal X-ray diffraction. In the solid, the pseudo-syn conformation is observed for the amide/thioamide groups, with the C=O and C=S double bonds oriented mutually parallel, favoring the occurrence of intramolecular O2···S1 chalcogen bond, as characterized by Atoms in Molecules (AIM) topological analysis. According to quantum chemical calculations, the pyrazolone group favors the formation of a dimer (Etot = -56.7 kJ/mol) which is mainly stabilized by C-H···O hydrogen bonds and π···π stacking interactions between the pyrazole and furan rings. The solid-state structure was analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that H···O hydrogen bonds and H···S/S···H contacts are the main electrostatic interactions. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP) and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding and π···π stacking interactions dominate the crystal packing.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science
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dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
AMINOPHENAZONE
dc.subject
CARBOXAMIDE
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DFT CALCULATIONS
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HIRSHFELD SURFACE ANALYSIS
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REARRANGEMENT
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SINGLE CRYSTAL XRD
dc.subject.classification
Química Inorgánica y Nuclear
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthesis of phenazone based carboxamide under thiourea reaction conditions. Molecular and crystal structure, Hirshfeld surface analysis and intermolecular interaction energies
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-02-14T12:11:17Z
dc.journal.volume
1278
dc.journal.pagination
1-12
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Khurshid, Asma. Quaid-I-Azam University; Pakistán
dc.description.fil
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
dc.description.fil
Fil: Shabir, Ghulam. Quaid-I-Azam University; Pakistán
dc.description.fil
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
dc.description.fil
Fil: Bolte, Michael. Goethe Universitat Frankfurt; Alemania
dc.description.fil
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
dc.journal.title
Journal of Molecular Structure
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.molstruc.2023.134948
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