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

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.