Diorganochalcogen(II) ligands of type [R2C(OH)CH2](2-Me2NCH2C6H4)E (E = S, Se, Te; R = Me, Ph), and their silver(I) complexes

• Ligands of type [R2C(OH)CH2](2-Me2NCH2C6H4)E [R = Me, Ph; E = S, Se, Te] are discussed.
• Their coordination behavior towards AgOTf was investigated.
• A complex fluxional behavior was observed in solution.
• The Ag(I) complexes are polar non-electrolytes in solution.
• [AgOTf{S[CH2C(OH)R2](C6H4CH2NMe2-2)}]2 has a dimeric structure.

Ligands of type [R2C(OH)CH2](2-Me2NCH2C6H4)E [R = Me, E = S (1), Se (2), Te (3); R = Ph, E = S (4), Se (5)] were obtained in the reactions of (2-Me2NCH2C6H4)ELi and the corresponding R2C(OH)CH2Cl (R = Me, Ph) reagent. The reactions between the ligands 1–3 and 5 with AgOTf (OTf = OSO2CF3), in a 1:1 M ratio, resulted in the silver(I) complexes [AgOTf{E[CH2C(OH)R2](C6H4CH2NMe2-2)}] [R = Me, E = S (6), Se (7), Te (8); R = Ph, E = Se (9)]. The new compounds 1–9 were investigated by solution NMR spectroscopy (1H, 19F, 77Se, 125Te, as appropriate). The ligands 1–5 were investigated also by 13C NMR. The IR spectra and the molar conductivity of the silver(I) complexes suggested a covalent nature of the Ag–OTf bond, while their ESI + MS spectra suggest the formation of dimeric species. Single crystal X-ray diffraction studies revealed a monomeric structure with intramolecular N⋯H–O hydrogen bonding for compound 5, while for the complex 6 dimeric associations formed by bridging ligands were found.

Ligands of type [R2C(OH)CH2](2-Me2NCH2C6H4)E (R = Me, Ph E = S, Se, Te) were prepared and structurally characterized. The coordination behavior of these ligands towards AgOTf was investigated both in solution and in solid state by different methods (multinuclear NMR, molar conductivity, IR and mass spectrometry, single crystal X-ray diffraction).Figure optionsDownload as PowerPoint slide