Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)

The presence of two different chromophores in benzothiazole molecule namely benzothiazole and aromatic rings lead to interesting chemical and biological properties that attract more researches on the compounds. Three new benzothiazolyl-benzoythiourea compounds namely 1-(1,3-benzothiazol-2-yl)-3-(ben...

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Main Authors:	Muhd Hafizi Zainal, Wun, Fui Mark-Lee, Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim
Format:	Article
Language:	English
Published:	Penerbit Universiti Kebangsaan Malaysia 2018
Online Access:	http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/1/07%20Muhd%20Hafizi%20.pdf

id	ukm-12080
recordtype	eprints
spelling	ukm-120802018-09-22T10:41:09Z http://journalarticle.ukm.my/12080/ Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea) Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim, The presence of two different chromophores in benzothiazole molecule namely benzothiazole and aromatic rings lead to interesting chemical and biological properties that attract more researches on the compounds. Three new benzothiazolyl-benzoythiourea compounds namely 1-(1,3-benzothiazol-2-yl)-3-(benzoylthiourea) (BBT), 1-(1,3-benzothiazol-2-yl)-3-(4-chlorobenzoylthiourea) (BBT-4Cl) and 1-(1,3-benzothiazol-2-yl)-3-(4-methoxybenzoylthiourea) (BBT-4OCH3) with different electron withdrawing substituents (R) at the para positions on the benzene ring of benzoylthiourea ring have been synthesized from the reaction of R-benzoyl isothiocyanate (R= H, Cl, and OCH3) and 2-aminobenzothiazole. The compounds were characterized by spectroscopic techniques (infrared, 1H proton NMR and UV-Vis). The IR spectra showed the frequency signals of n (C=O), n (C=S), n (N-H) at 1664-1673, 1238-1249 and 3031-3055 cm-1, respectively. The 1H proton NMR spectra showed the presence of N-H amine and amide signals in the region of (12.14-12.35) and (14.17-14.43) ppm, respectively. The proton signals of the two benzothiazole and benzoylthiourea moieties appear at 7.08-8.16 ppm. A theoretical study based on Density Functional Theory (DFT) and Time-Dependent (TD) DFT was conducted to optimize the geometrical structure and investigate the electronic properties of title compounds. The highest occupied molecular orbital (HOMO) was found on the benzothiazole moiety; while, the lowest-unoccupied molecular orbital (LUMO) was located at the benzoylthiourea fragment. The DFT optimized structures possessed an intramolecular hydrogen bonding and the types of para substituents used influenced the properties of hydrogen bonding. Penerbit Universiti Kebangsaan Malaysia 2018-05 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/12080/1/07%20Muhd%20Hafizi%20.pdf Muhd Hafizi Zainal, and Wun, Fui Mark-Lee and Syahidah Mohd Tahir, and Ishak Ahmad, and Mohammad Kassim, (2018) Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea). Sains Malaysiana, 47 (5). pp. 923-929. ISSN 0126-6039 http://www.ukm.my/jsm/english_journals/vol47num5_2018/contentsVol47num5_2018.html
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Kebangasaan Malaysia
building	UKM Institutional Repository
collection	Online Access
language	English
description	The presence of two different chromophores in benzothiazole molecule namely benzothiazole and aromatic rings lead to interesting chemical and biological properties that attract more researches on the compounds. Three new benzothiazolyl-benzoythiourea compounds namely 1-(1,3-benzothiazol-2-yl)-3-(benzoylthiourea) (BBT), 1-(1,3-benzothiazol-2-yl)-3-(4-chlorobenzoylthiourea) (BBT-4Cl) and 1-(1,3-benzothiazol-2-yl)-3-(4-methoxybenzoylthiourea) (BBT-4OCH3) with different electron withdrawing substituents (R) at the para positions on the benzene ring of benzoylthiourea ring have been synthesized from the reaction of R-benzoyl isothiocyanate (R= H, Cl, and OCH3) and 2-aminobenzothiazole. The compounds were characterized by spectroscopic techniques (infrared, 1H proton NMR and UV-Vis). The IR spectra showed the frequency signals of n (C=O), n (C=S), n (N-H) at 1664-1673, 1238-1249 and 3031-3055 cm-1, respectively. The 1H proton NMR spectra showed the presence of N-H amine and amide signals in the region of (12.14-12.35) and (14.17-14.43) ppm, respectively. The proton signals of the two benzothiazole and benzoylthiourea moieties appear at 7.08-8.16 ppm. A theoretical study based on Density Functional Theory (DFT) and Time-Dependent (TD) DFT was conducted to optimize the geometrical structure and investigate the electronic properties of title compounds. The highest occupied molecular orbital (HOMO) was found on the benzothiazole moiety; while, the lowest-unoccupied molecular orbital (LUMO) was located at the benzoylthiourea fragment. The DFT optimized structures possessed an intramolecular hydrogen bonding and the types of para substituents used influenced the properties of hydrogen bonding.
format	Article
author	Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim,
spellingShingle	Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim, Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
author_facet	Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim,
author_sort	Muhd Hafizi Zainal,
title	Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
title_short	Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
title_full	Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
title_fullStr	Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
title_full_unstemmed	Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)
title_sort	experimental and dft investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-benzothiazol-2- y1)-3-(r-benzoylthiourea)
publisher	Penerbit Universiti Kebangsaan Malaysia
publishDate	2018
url	http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/1/07%20Muhd%20Hafizi%20.pdf
first_indexed	2023-09-18T20:01:49Z
last_indexed	2023-09-18T20:01:49Z
_version_	1777406898735153152

Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-Benzothiazol-2- y1)-3-(R-benzoylthiourea)

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