Triorganophosphinegold(I) Carbonimidothioates

Abstract

The title compounds, R~PAuSC(=NP~)OR', R = Et, Ph or Cy and R' = Me, Et, Pr, pri or Cy, have been prepared and characterized by spectroscopic methods (i.r., 'H and 13c n.m.r. and f.a.b. m.s.) and, in the case of the R = Ph and R' = Me compound, by single-crystal X-ray diffraction methods. The spectroscopic data are consistent with the R3PAu moiety being coordinated by the sulfur atom of the thiolate ligand. This has been confirmed by an X-ray study on PhaPAuSC(=NPh)OMe which shows the gold atom to be linearly coordinated by the phosphorus and sulfur atoms; Au-P(1) 2.258 (1), Au-S(1) 2.301(1) A and P-Au-S 177.7(1)'. Crystals of PhsPAuSC(=NPh)OMe are triclinic, space group pi, with unit cell dimensions: a 10.825(1), b 12.553(2), c 8.914(2) a, a 97.86(2), , B 93.79(1), y 88.60(1)O, V 1197.1 fi3, Z 2. The structure was refined by a full-matrix least-squares procedure to R 0.028 for 4409 reflections with I > 2.5a(I). A J(P-H). N-Ph resonances overlap with P-Ph resonances. Obscured.1989, 1803.

Synthesis, structures and in vitro cytotoxicity of some platinum(II) complexes containing thiocarbamate esters

“…92.20(11)°and 87.80(11)°, deviate only very slightly from the 90°e xpected for square planar geometry. Small deviations from the ideal geometry may be traced to the presence of a close intramolecular PÁ Á ÁO1 separation = 3.036(9) Å; such metalÁ Á ÁO interactions are often seen in the structural chemistry of these ligands [8][9][10]. The Pt-P bond length of 2.272(3) Å in 4 is similar to those observed in other PTA metal complexes and in the same way, the Pt-S distance of 2.345(3) Å is similar to that found in other complexes containing S-coordinated aryl thiocarbamate esters.…”

“…The palladium complex [Pd{jN,S-PhN@C(S)OMe}{jS-PhN@C(S)OMe}(PPh 3 )] is the only example in which both coordination modes (anionic S À ligand and N,S-chelate ligand) are present in the same molecule [7]. To the best of our knowledge, the only known complexes of this type that have been prepared by direct reaction of the neutral thiocarbamate esters with transition metal chloride precursors in the presence of base are the above mentioned Pd chelates as well as the mono-and dinuclear gold(I) phosphine complexes [Au{ArN@C(S)OMe}(P)] and [Au 2 {ArN@C(S)OMe} 2 (l-PP)] (P and PP = mono-and bidentate phosphine ligands, respectively) reported by Tiekink [8][9][10]. Ever since the accidental discovery of the cytotoxic properties of cis-[PtCl 2 (NH 3 ) 2 ] by Rosenberg almost 40 years ago [11], cytotoxicity studies of many platinum compounds have been carried out [12].…”

G 2 /M cell cycle arrest on HT-29 cancer cells and toxicity assessment of triphenylphosphanegold(I) carbonimidothioates, Ph 3 PAu[SC(OR) = NPh], R = Me, Et, and iPr, during zebrafish development

“…were prepared in high yields as described previously [22] and following well established protocols [23], i.e., via the reaction of Ph3PAuCl with the respective ROC(=S)N(H)Ph ligand [24] in the presence of base, and exhibited the same spectroscopic ( 1 H, 13 C{ 1 H} and 31 P{ 1 H}…”

A conformational polymorph of Ph3PAu[SC(OEt)=NPh] featuring an intramolecular Au···π interaction

“…The measured pattern of the newly synthesised material did not match that calculated from the literature structure of (I), reported to be recrystallised from slow evaporations of its chloroform solution [1,31]. Accordingly, a single crystal structure analysis was conducted revealing a second polymorphic form for (I), i.e.…”

“…Form α of (I) was isolated from its CHCl 3 solution and reported to have a melting point of 137-139 °C [1,31]. Form β, isolated from the methanolic reaction mixture Tab.…”