Towards the water solubilization of [Pt₂(μ-S)₂(PPh₃)₄] derivatives by polyether functionalization – a synthetic and mass spectrometric investigation

Abstract

Synthetic methods have been developed to append polyether chains onto the nucleophilic platinum (II) sulfide complex [Pt 2 (μ-S) 2 (PPh 3 ) 4 ] through alkylation reactions of a sulfide ligand. Reaction of [Pt 2 (μ-S) 2 (PPh 3 ) 4 ] with Br(CH 2 ) 2 NHC(O)NH(CH 2 ) 2 OMe gave the monoalkylated model complex [Pt 2 (μ-S){μ-S(CH 2 ) 2 NHC(O)NH(CH 2 ) 2 OMe}(PPh 3 ) 4 ] + , isolated as its PF 6 À salt. Extension of this methodology to the polyether-derived alkylating agent Br(CH 2 ) 2 NHC(O)NHCHMeCH 2 (OCHMeCH 2 ) n OCH 2 CH 2 OMe derived from the polyether amine Jeffamine ® M600 gave the cation [Pt 2 (μ-S){μ-S(CH 2 ) 2 NHC(O)NHCHMeCH 2 (OCHMeCH 2 ) n OCH 2 CH 2 OMe}(PPh 3 ) 4 ] + , isolated as its BPh 4 À salt and characterized by ESI MS and 31 P{ 1 H} NMR spectroscopy. Reaction of [Pt 2 (μ-S) 2 (PPh 3 ) 4 ] with the chloro-PEG Me(OCH 2 CH 2 ) n Cl (derived from MeOPEG 350) in the presence of NaBr in refluxing methanol proceeded slowly, giving [Pt 2 (μ-S){μ-S(CH 2 CH 2 O) n Me} (PPh 3 ) 4 ] + , isolated as its BPh 4 À salt. The aqueous solubility of a selection of compounds was determined.The functionalisation of the platinum(II) sulfide complex [Pt 2 (μ-S) 2 (PPh 3 ) 4 ] with polyether-based alkylating agents, monitored by ESI mass spectrometry, leads to a series of novel polyether-thiolate complexes.

Novel 3‐Hydroxy‐2‐naphthoic hydrazone and Ni(II), Co(II) and Cu(II) Complexes: Synthesis, Spectroscopic Characterization, Antimicrobial, DNA Cleavage and Computational Studies

“…2 mL using methanol. The mass spectra were recorded on a Waters Micromass Q‐TOF II Mass Spectrometer, in positive ion mode, using pneumatically assisted electrospray ionization: capillary of voltage, 2900 V; sample cone voltage, 15 V; extraction voltage, 1 V; source temperature, 80 °C; desolvation temperature, 160 °C; cone gas flow, 100Lh −1 ; desolvation gas flow, 100Lh −1 ; collision voltage, 2 V; MCP voltage, 2400 V. No smoothening of the data was performed, and comparison of observed and calculated isotope patterns was used in the ion assignment.…”