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 B. Zainal, Wun Fui Mark-Lee, Syahidah Mohd Tahir, Ishak Ahmad, Mohammad Kassim

Research output: Contribution to journalArticle

Abstract

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.

Translated title of the contributionExperimental 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)
LanguageMalay
Pages923-929
Number of pages7
JournalSains Malaysiana
Volume47
Issue number5
DOIs
Publication statusPublished - 1 May 2018

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Density functional theory
Hydrogen bonds
Protons
Electrons
Molecular orbitals
Nuclear magnetic resonance
Chromophores
Benzene
Amides
Electronic properties
Amines
Infrared radiation
Molecules
benzothiazole

Keywords

    ASJC Scopus subject areas

    • General

    Cite this

    (Uji kaji dan penyiasatan DFT mengenai pengaruh penderma/penerima elektron pada interaksi ikatan hidrogen dalam 1- (1,3-benzotiazol-2-yl) -3- (R-benzoylthiourea)). / Zainal, Muhd Hafizi B.; Mark-Lee, Wun Fui; Tahir, Syahidah Mohd; Ahmad, Ishak; Kassim, Mohammad.

    In: Sains Malaysiana, Vol. 47, No. 5, 01.05.2018, p. 923-929.

    Research output: Contribution to journalArticle

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    abstract = "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.",
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    AU - Zainal, Muhd Hafizi B.

    AU - Mark-Lee, Wun Fui

    AU - Tahir, Syahidah Mohd

    AU - Ahmad, Ishak

    AU - Kassim, Mohammad

    PY - 2018/5/1

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    N2 - 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.

    AB - 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.

    KW - Benzothiazolyl-benzoylthiourea

    KW - DFT

    KW - Electron donating groups

    KW - Electron withdrawing groups

    KW - Hydrogen bonding interactions

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