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DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control

A well-known process, called the advanced oxidation process, has been effectively used to study the oxidation mechanism of pharmaceutical wastes. The strong reactivity of hydroxyl radicals used in this process gradually oxidizes organic molecules into nontoxic products. Hence, the mechanistic detail...

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Main Authors: Bibi, Shamsa, Saleem, Aamna, Rehman, Shafiq Ur, Bhatti, Ijaz Ahmad, Iqbal, Muhammad Adnan, Bashir, Shahid, Quan, Bai Fu, Nadeem, Raziya
Format: Article
Published: WILEY 2023
Subjects:
QC Physics
QD Chemistry
Online Access:http://eprints.um.edu.my/38858/
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spelling my.um.eprints.388582023-11-23T00:30:02Z http://eprints.um.edu.my/38858/ DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control Bibi, Shamsa Saleem, Aamna Rehman, Shafiq Ur Bhatti, Ijaz Ahmad Iqbal, Muhammad Adnan Bashir, Shahid Quan, Bai Fu Nadeem, Raziya QC Physics QD Chemistry A well-known process, called the advanced oxidation process, has been effectively used to study the oxidation mechanism of pharmaceutical wastes. The strong reactivity of hydroxyl radicals used in this process gradually oxidizes organic molecules into nontoxic products. Hence, the mechanistic details of secnidazole, 1-(2-hydroxypropy1)-2-methy1-5-nitroimidazole, oxidation, promoted by (OH)-O-center dot have been studied under the M06-2X method and 6-311 G (d,p) level of theory, using density functional theory. Secnidazole molecule has been decomposed by oxidation of the isopropanol to an -COOH group, resulting in (2-methyl-5-nitro-imidazol-1-yl) acetic acid, which is further oxidized to (5-hydroxy-2-methylimidazol-1-yl) acetic acid, by the action of (OH)-O-center dot. Furthermore, nitro and methyl groups present as substituents to the five-membered ring are replaced by hydroxyl groups, forming 1-(2-hydroxypropyl)-2-methyl-1H-imidazol-5-ol and 1-(2-hydroxypropyl)-5-nitro-1H-imidazol-2-ol, respectively. The optimized geometries of intermediates, transition states, and free energy surfaces have been found valuable in interpreting the details of the elimination mechanism. Fukui functional analysis has disclosed the reactivities of each site of SNZ. The systematic calculations on initial products and intermediates have shown significant exothermic properties. WILEY 2023-04 Article PeerReviewed Bibi, Shamsa and Saleem, Aamna and Rehman, Shafiq Ur and Bhatti, Ijaz Ahmad and Iqbal, Muhammad Adnan and Bashir, Shahid and Quan, Bai Fu and Nadeem, Raziya (2023) DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control. Journal of Physical Organic Chemistry, 36 (4). ISSN 0894-3230, DOI https://doi.org/10.1002/poc.4480 <https://doi.org/10.1002/poc.4480>. 10.1002/poc.4480
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QC Physics
QD Chemistry
spellingShingle QC Physics
QD Chemistry
Bibi, Shamsa
Saleem, Aamna
Rehman, Shafiq Ur
Bhatti, Ijaz Ahmad
Iqbal, Muhammad Adnan
Bashir, Shahid
Quan, Bai Fu
Nadeem, Raziya
DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
description A well-known process, called the advanced oxidation process, has been effectively used to study the oxidation mechanism of pharmaceutical wastes. The strong reactivity of hydroxyl radicals used in this process gradually oxidizes organic molecules into nontoxic products. Hence, the mechanistic details of secnidazole, 1-(2-hydroxypropy1)-2-methy1-5-nitroimidazole, oxidation, promoted by (OH)-O-center dot have been studied under the M06-2X method and 6-311 G (d,p) level of theory, using density functional theory. Secnidazole molecule has been decomposed by oxidation of the isopropanol to an -COOH group, resulting in (2-methyl-5-nitro-imidazol-1-yl) acetic acid, which is further oxidized to (5-hydroxy-2-methylimidazol-1-yl) acetic acid, by the action of (OH)-O-center dot. Furthermore, nitro and methyl groups present as substituents to the five-membered ring are replaced by hydroxyl groups, forming 1-(2-hydroxypropyl)-2-methyl-1H-imidazol-5-ol and 1-(2-hydroxypropyl)-5-nitro-1H-imidazol-2-ol, respectively. The optimized geometries of intermediates, transition states, and free energy surfaces have been found valuable in interpreting the details of the elimination mechanism. Fukui functional analysis has disclosed the reactivities of each site of SNZ. The systematic calculations on initial products and intermediates have shown significant exothermic properties.
format Article
author Bibi, Shamsa
Saleem, Aamna
Rehman, Shafiq Ur
Bhatti, Ijaz Ahmad
Iqbal, Muhammad Adnan
Bashir, Shahid
Quan, Bai Fu
Nadeem, Raziya
author_facet Bibi, Shamsa
Saleem, Aamna
Rehman, Shafiq Ur
Bhatti, Ijaz Ahmad
Iqbal, Muhammad Adnan
Bashir, Shahid
Quan, Bai Fu
Nadeem, Raziya
author_sort Bibi, Shamsa
title DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
title_short DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
title_full DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
title_fullStr DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
title_full_unstemmed DFT study of oxidation mechanism of secnidazole as an emerging contaminant: Application as STI control
title_sort dft study of oxidation mechanism of secnidazole as an emerging contaminant: application as sti control
publisher WILEY
publishDate 2023
url http://eprints.um.edu.my/38858/
_version_ 1783876674046132224
score 13.211869

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