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: Contribution to journalArticle

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

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: Contribution to journalArticle

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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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    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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