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A novel benzoylthiourea derivative with a triazinethione moiety: Synthesis and coordination with the organometallic fac-[Re(CO)3]+ core


Mukiza, Janvier; Braband, Henrik; Bolliger, Robin; Blacque, Olivier; Alberto, Roger; Nkurunziza, Jean Baptiste (2021). A novel benzoylthiourea derivative with a triazinethione moiety: Synthesis and coordination with the organometallic fac-[Re(CO)3]+ core. Inorganica Chimica Acta, 516:120116.

Abstract

Benzoylthiourea derivatives containing heterocyclic moiety strongly coordinate and stabilize the organometallic fac-[Re(CO3](+) core forming both monomer and multimer organorhenium(I) complexes. The reaction of isophthaloyl dichloride with potassium thiocyanate in acetone followed by addition of diphenylamine led to a novel benzoylthiourea derivative with triazinethione moiety ligand, typically 3-(4-(diphenylamino)-6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl)N(diphenylcarbamothioyebenzamide (H2L). The purity and retention time of the ligand H2L were assessed by ultraperfomance liquid chromatography (UPLC) and analyzed by H-1 NMR, C-13 NMR, infra-red (IR) and liquid chromatography mass spectrometry (ESI-MS). The coordination mode of H2L to the organometallic fac-[Re(CO)(3)](+) core was investigated by reacting the ligand with [Re(CO) 5 Br] in toluene. The reaction led to a dimeric complex [(mu-H2L)(2)(Re(CO)(3)Br)(2)] in which the H2L coordinates to each of the fac-[Re(CO)(3)](+) units as neutral monodentate and S-donor chelate. The dimer [(mu-H2L)(2)(Re(CO)(3)Br)(2)] was analyzed by H-1 NMR, infra-red (IR), high resolution mass spectrometry (HR-ESI-MS) and single crystal X-Ray crystallography.

Abstract

Benzoylthiourea derivatives containing heterocyclic moiety strongly coordinate and stabilize the organometallic fac-[Re(CO3](+) core forming both monomer and multimer organorhenium(I) complexes. The reaction of isophthaloyl dichloride with potassium thiocyanate in acetone followed by addition of diphenylamine led to a novel benzoylthiourea derivative with triazinethione moiety ligand, typically 3-(4-(diphenylamino)-6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl)N(diphenylcarbamothioyebenzamide (H2L). The purity and retention time of the ligand H2L were assessed by ultraperfomance liquid chromatography (UPLC) and analyzed by H-1 NMR, C-13 NMR, infra-red (IR) and liquid chromatography mass spectrometry (ESI-MS). The coordination mode of H2L to the organometallic fac-[Re(CO)(3)](+) core was investigated by reacting the ligand with [Re(CO) 5 Br] in toluene. The reaction led to a dimeric complex [(mu-H2L)(2)(Re(CO)(3)Br)(2)] in which the H2L coordinates to each of the fac-[Re(CO)(3)](+) units as neutral monodentate and S-donor chelate. The dimer [(mu-H2L)(2)(Re(CO)(3)Br)(2)] was analyzed by H-1 NMR, infra-red (IR), high resolution mass spectrometry (HR-ESI-MS) and single crystal X-Ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Inorganic Chemistry
Physical Sciences > Materials Chemistry
Uncontrolled Keywords:Materials Chemistry, Inorganic Chemistry, Physical and Theoretical Chemistry
Language:English
Date:1 February 2021
Deposited On:29 Sep 2021 15:06
Last Modified:30 Sep 2021 20:00
Publisher:Elsevier
ISSN:0020-1693
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/j.ica.2020.120116
Project Information:
  • : FunderUniversity of Zurich
  • : Grant ID
  • : Project Title

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