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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| Format: | Article |
| Language: | English |
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Penerbit Universiti Kebangsaan Malaysia
2018
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| Online Access: | http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/1/07%20Muhd%20Hafizi%20.pdf |
| _version_ | 1848812903927382016 |
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| author | Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim, |
| author_facet | Muhd Hafizi Zainal, Wun, Fui Mark-Lee Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim, |
| author_sort | Muhd Hafizi Zainal, |
| building | UKM Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-15T00:09:42Z |
| format | Article |
| id | oai:generic.eprints.org:12080 |
| institution | Universiti Kebangasaan Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T00:09:42Z |
| publishDate | 2018 |
| publisher | Penerbit Universiti Kebangsaan Malaysia |
| recordtype | eprints |
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| spelling | oai:generic.eprints.org: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 |
| 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) |
| 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_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_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_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) |
| url | http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/ http://journalarticle.ukm.my/12080/1/07%20Muhd%20Hafizi%20.pdf |