Staff View: Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations

Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations

Benzodiazepines derivatives have been reported for their broad spectrum of biological applications. These derivatives are also being investigated for their supporting activity against human cancers. The title compound 5-(3-Methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one has bee...

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Main Authors:	Naveena, S., Kumara, K., Al-Maqtari, H. M., Deepa Urs, M. V., Jamalis, J., Reddy, K. R., Lingegowda, N. S., Lokanath, N. K.
Format:	Article
Published:	Elsevier Ltd. 2019
Subjects:	QD Chemistry
Online Access:	http://eprints.utm.my/id/eprint/90274/ http://dx.doi.org/10.1016/j.cdc.2019.100292
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spelling	my.utm.902742021-03-31T06:31:33Z http://eprints.utm.my/id/eprint/90274/ Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations Naveena, S. Kumara, K. Al-Maqtari, H. M. Deepa Urs, M. V. Jamalis, J. Reddy, K. R. Lingegowda, N. S. Lokanath, N. K. QD Chemistry Benzodiazepines derivatives have been reported for their broad spectrum of biological applications. These derivatives are also being investigated for their supporting activity against human cancers. The title compound 5-(3-Methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one has been synthesized, characterized using 1H NMR, 13C NMR, IR techniques and finally the structure was confirmed by single crystal X-ray diffraction studies. The single crystals of the compound were obtained using ethanol as crystallization solvent. The compound C18H18N2O2 crystallizes in the orthorhombic crystal system with P212121 space group. The crystal structure of the title compound is stabilized by Nsingle bondH···O intermolecular hydrogen bond and p···p interactions. The structure also exhibits one dimensional chain stacking along a-axis through intermolecular interactions. These molecular interactions were then quantified using Hirshfeld surface analysis to understand their nature of involvement in interaction with other molecules. The analysis of the fingerprint plots revealed that the H…H (58.7%) interactions has the major contribution to the total molecular surface. Further, the electronic properties of the title compound were studied by computing the frontier molecular orbital energies using density functional theory calculations with B3LYP/6-311 + G (d, p) level basis set. Finally, the molecular electrostatic potential map was generated and the chemical reactive sites were identified to understand the molecular surface properties. Elsevier Ltd. 2019-12 Article PeerReviewed Naveena, S. and Kumara, K. and Al-Maqtari, H. M. and Deepa Urs, M. V. and Jamalis, J. and Reddy, K. R. and Lingegowda, N. S. and Lokanath, N. K. (2019) Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations. Chemical Data Collections, 24 . ISSN 1547-5271 http://dx.doi.org/10.1016/j.cdc.2019.100292 DOI: 10.1016/j.cdc.2019.100292
institution	Universiti Teknologi Malaysia
building	UTM Library
collection	Institutional Repository
continent	Asia
country	Malaysia
content_provider	Universiti Teknologi Malaysia
content_source	UTM Institutional Repository
url_provider	http://eprints.utm.my/
topic	QD Chemistry
spellingShingle	QD Chemistry Naveena, S. Kumara, K. Al-Maqtari, H. M. Deepa Urs, M. V. Jamalis, J. Reddy, K. R. Lingegowda, N. S. Lokanath, N. K. Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
description	Benzodiazepines derivatives have been reported for their broad spectrum of biological applications. These derivatives are also being investigated for their supporting activity against human cancers. The title compound 5-(3-Methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one has been synthesized, characterized using 1H NMR, 13C NMR, IR techniques and finally the structure was confirmed by single crystal X-ray diffraction studies. The single crystals of the compound were obtained using ethanol as crystallization solvent. The compound C18H18N2O2 crystallizes in the orthorhombic crystal system with P212121 space group. The crystal structure of the title compound is stabilized by Nsingle bondH···O intermolecular hydrogen bond and p···p interactions. The structure also exhibits one dimensional chain stacking along a-axis through intermolecular interactions. These molecular interactions were then quantified using Hirshfeld surface analysis to understand their nature of involvement in interaction with other molecules. The analysis of the fingerprint plots revealed that the H…H (58.7%) interactions has the major contribution to the total molecular surface. Further, the electronic properties of the title compound were studied by computing the frontier molecular orbital energies using density functional theory calculations with B3LYP/6-311 + G (d, p) level basis set. Finally, the molecular electrostatic potential map was generated and the chemical reactive sites were identified to understand the molecular surface properties.
format	Article
author	Naveena, S. Kumara, K. Al-Maqtari, H. M. Deepa Urs, M. V. Jamalis, J. Reddy, K. R. Lingegowda, N. S. Lokanath, N. K.
author_facet	Naveena, S. Kumara, K. Al-Maqtari, H. M. Deepa Urs, M. V. Jamalis, J. Reddy, K. R. Lingegowda, N. S. Lokanath, N. K.
author_sort	Naveena, S.
title	Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
title_short	Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
title_full	Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
title_fullStr	Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
title_full_unstemmed	Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations
title_sort	synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and dft calculations
publisher	Elsevier Ltd.
publishDate	2019
url	http://eprints.utm.my/id/eprint/90274/ http://dx.doi.org/10.1016/j.cdc.2019.100292
_version_	1696976286564483072
score	13.211869

Synthesis, characterization crystal and molecular structure studies of 5-(3-methylbenzoyl)-4-methyl-1,3,4,5-tetrahydro-2h-1,5-benzodiazepin-2-one: hirshfeld surface analysis and DFT calculations

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