Synthesis and structural characterization of N-bromobenzoyl-N’-(1,10-phenanthrolin-5-yl)thiourea derivatives

Rosidah Shardin, Siew San Tan, Mohammad B. Kassim

Research output: Research - peer-reviewArticle

Abstract

Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10-phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-p-BrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na]+ and [BrBT]+, respectively. The presence of a v(NH) (3389-3599 cm-1) and the disappearance of ν(NH2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm-1 compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269-270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition,13C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.

Translated title of the contributionSynthesis and structural characterization of N-bromobenzoyl-N’-(1,10-phenanthrolin-5-yl)thiourea derivatives
LanguageMalay
Pages60-71
Number of pages12
JournalMalaysian Journal of Analytical Sciences
Volume21
Issue number1
DOIs
StatePublished - 1 Feb 2017

Fingerprint

Thiourea
Derivatives
Luminescence
1,10-phenanthroline
Phenanthrolines
Molecular structure
Cyclic voltammetry
Stretching
Amines
Mass spectrometry
Protons
Substitution reactions
Crystal structure
Nuclear magnetic resonance
Ions
Ligands
Infrared radiation
Atoms
Chemical analysis

Keywords

    ASJC Scopus subject areas

    • Analytical Chemistry

    Cite this

    Sintesis dan Penentuan struktur ligan terbitan N-bromobenzoil-N’-(1,10-fenantrolin-5-il) tiourea. / Shardin, Rosidah; Tan, Siew San; Kassim, Mohammad B.

    In: Malaysian Journal of Analytical Sciences, Vol. 21, No. 1, 01.02.2017, p. 60-71.

    Research output: Research - peer-reviewArticle

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    abstract = "Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10-phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-p-BrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na]+ and [BrBT]+, respectively. The presence of a v(NH) (3389-3599 cm-1) and the disappearance of ν(NH2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm-1 compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269-270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition,13C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.",
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    AU - Kassim,Mohammad B.

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    N2 - Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10-phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-p-BrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na]+ and [BrBT]+, respectively. The presence of a v(NH) (3389-3599 cm-1) and the disappearance of ν(NH2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm-1 compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269-270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition,13C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.

    AB - Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10-phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-p-BrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na]+ and [BrBT]+, respectively. The presence of a v(NH) (3389-3599 cm-1) and the disappearance of ν(NH2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm-1 compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269-270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition,13C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.

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