Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation

In this study, a novel trans-(1E,2E)-benzil-O,O-dimethylsulfonyl dioxime (BDMDO) monomer was prepared via a one-step dehydrochlorination reaction. BDMDO was characterized by 1H and 13C NMR, UV–Vis, and FT-IR spectroscopies, CHN elemental analysis, mass spectrometry, energy-dispersive X-ray spectrosc...

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Main Authors: Nabil Al-Zaqri, Ali Alsalme, Fahad Alharthi, Afnan Al-Taleb, Ahmed M. Boshaala, Ahmed Chetouni, Abdelkader Zarrouk, Ismail Warad
Format: Article
Language:English
Published: Elsevier 2021-03-01
Series:Journal of King Saud University: Science
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S1018364720304110
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author Nabil Al-Zaqri
Ali Alsalme
Fahad Alharthi
Afnan Al-Taleb
Ahmed M. Boshaala
Ahmed Chetouni
Abdelkader Zarrouk
Ismail Warad
author_facet Nabil Al-Zaqri
Ali Alsalme
Fahad Alharthi
Afnan Al-Taleb
Ahmed M. Boshaala
Ahmed Chetouni
Abdelkader Zarrouk
Ismail Warad
author_sort Nabil Al-Zaqri
collection DOAJ
description In this study, a novel trans-(1E,2E)-benzil-O,O-dimethylsulfonyl dioxime (BDMDO) monomer was prepared via a one-step dehydrochlorination reaction. BDMDO was characterized by 1H and 13C NMR, UV–Vis, and FT-IR spectroscopies, CHN elemental analysis, mass spectrometry, energy-dispersive X-ray spectroscopy, and TGA. According to the X-ray diffraction data, the BDMDO crystal structure was solved as a trans-isomer dioxime. The lattice structure was stabilized by two types of H-bonds and a sufficient number of interesting non-covalent supramolecular interactions such as the CH⋯HC bonds. Molecular electrostatic potential measurements and Hirschfeld surface analysis were performed to understand these interaction modes. The cis–trans isomerization in BDMDO as well as the structural, vibrational, NMR, highest occupied molecular orbital/lowest unoccupied molecular orbital bandgap, density of states, and electronic properties were computed by the density functional theory and subsequently compared with available experimental 1H and 13C NMR, UV–Vis, and FT-IR spectral data. The thermogravimetric/derivative thermogravimetric behavior of BDMDO was determined experimentally under an open-room atmosphere.
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spelling doaj.art-fbef0fe00b1041f48d4da80ac2a74baa2022-12-21T19:45:04ZengElsevierJournal of King Saud University: Science1018-36472021-03-01332101298Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigationNabil Al-Zaqri0Ali Alsalme1Fahad Alharthi2Afnan Al-Taleb3Ahmed M. Boshaala4Ahmed Chetouni5Abdelkader Zarrouk6Ismail Warad7Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; Corresponding authors.Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Benghazi University, P O Box 1308, Benghazi, LibyaLaboratoire de Chimie Analytique Appliquée, Matériaux et Environnement (LC2AME), Faculté des Sciences, Université Mohamed I, 60 000 Oujda, MoroccoLaboratory of Materials, Nanotechnology and Environment, Faculty of Sciences, Mohammed V University, Av. Ibn Battouta, Box 1014 Agdal-Rabat, MoroccoDepartment of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine; Corresponding authors.In this study, a novel trans-(1E,2E)-benzil-O,O-dimethylsulfonyl dioxime (BDMDO) monomer was prepared via a one-step dehydrochlorination reaction. BDMDO was characterized by 1H and 13C NMR, UV–Vis, and FT-IR spectroscopies, CHN elemental analysis, mass spectrometry, energy-dispersive X-ray spectroscopy, and TGA. According to the X-ray diffraction data, the BDMDO crystal structure was solved as a trans-isomer dioxime. The lattice structure was stabilized by two types of H-bonds and a sufficient number of interesting non-covalent supramolecular interactions such as the CH⋯HC bonds. Molecular electrostatic potential measurements and Hirschfeld surface analysis were performed to understand these interaction modes. The cis–trans isomerization in BDMDO as well as the structural, vibrational, NMR, highest occupied molecular orbital/lowest unoccupied molecular orbital bandgap, density of states, and electronic properties were computed by the density functional theory and subsequently compared with available experimental 1H and 13C NMR, UV–Vis, and FT-IR spectral data. The thermogravimetric/derivative thermogravimetric behavior of BDMDO was determined experimentally under an open-room atmosphere.http://www.sciencedirect.com/science/article/pii/S1018364720304110DioximeXRDHSAMEPNMR
spellingShingle Nabil Al-Zaqri
Ali Alsalme
Fahad Alharthi
Afnan Al-Taleb
Ahmed M. Boshaala
Ahmed Chetouni
Abdelkader Zarrouk
Ismail Warad
Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
Journal of King Saud University: Science
Dioxime
XRD
HSA
MEP
NMR
title Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
title_full Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
title_fullStr Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
title_full_unstemmed Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
title_short Synthesis, physicochemical, thermal, XDR/HSA-interactions of Trans-(1E,2E)-Benzil-O,O-dimethylsulfonyl dioxime: Cis-trans isomerization, DFT and TD-DFT investigation
title_sort synthesis physicochemical thermal xdr hsa interactions of trans 1e 2e benzil o o dimethylsulfonyl dioxime cis trans isomerization dft and td dft investigation
topic Dioxime
XRD
HSA
MEP
NMR
url http://www.sciencedirect.com/science/article/pii/S1018364720304110
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