627-44-1Relevant articles and documents
French et al.
, p. 2228,2235 (1964)
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Honeycutt,Riddle
, p. 2593 (1959)
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Transmetalation of Pentafluorophenylmercury Derivatives with Organylmagnesium Bromides
Bardin
, p. 1406 - 1408 (2019/08/21)
The reactions of pentafluorophenylmercury derivatives with organomagnesium compounds have been studied. The interaction of pentafluorophenylmercury chloride with RMgBr (R = Et, Ph) has afforded diphenyl- and diethylmercury or phenylmercury chloride, besides the expected product (C6F5HgR). The results have been explained by the transmetalation of C6F5HgR with the Grignard reagent, followed by the reaction of the resulting C6F5MgX (X = Br, C6F5) with pentafluorophenylmercury chloride. Transmetalation of (C6F5)2Hg with organylmagnesium bromides has led to the formation of C6F5MgX and R2Hg.
Cleavage of Hg-C Bonds of Organomercurials Induced by ImOHSe via Two Distinct Pathways
Banerjee, Mainak,Roy, Gouriprasanna
supporting information, p. 12739 - 12750 (2017/11/14)
We show that the N-methylimidazole-based selone ImOHSe having an N-CH2CH2OH substituent has the remarkable ability to degrade methylmercury by two distinct pathways. Under basic conditions, ImOHSe converts MeHgCl into biologically inert HgSe nanoparticles and Me2Hg via the formation of an unstable intermediate (MeHg)2Se (pathway I). However, under neutral conditions, in the absence of any base, ImOHSe facilitates the cleavage of the Hg-C bond of MeHgCl at room temperature (23 °C), leading to the formation of a stable cleaved product, the tetracoordinated mononuclear mercury compound (ImOHSe)2HgCl2 and Me2Hg (pathway II). The initial rate of Hg-C bond cleavage of MeHgCl induced by ImOHSe is almost 2-fold higher than the initial rate observed by ImMeSe. Moreover, we show that ImYSe (Y = OH, Me) has an excellent ability to dealkylate Me2Hg at room temperature. Under acidic conditions, in the presence of excess ImYSe, the volatile and toxic Me2Hg further decomposes to the tetracoordinated mononuclear mercury compound [(ImYSe)4Hg]2+. In addition, the treatment of ImOHSe with MeHgCys or MeHgSG in phosphate buffer (pH 8.5) afforded water-soluble Hg(SeS) nanoparticles via unusual ligand exchange reactions, whereas its derivative ImOMeSe or ImMeSe, lacking the N-CH2CH2OH substituent, failed to produce Hg(SeS) nanoparticles under identical reaction conditions.
Organomercury Compounds. XXXI. Preparations and 199Hg N.M.R. Spectra of Organomercury Derivatives of 2-Phenylpyridine, Benzoquinoline, 1-Phenylpyrazole and 3,4,5-Trimethyl-1-phenylpyrazole, and the X-Ray Crystal Structure of Bismercury
Black, David St. C.,Deacon, Glen B.,Edwards, Gavin L.,Gatehouse, Bryan M.
, p. 1323 - 1336 (2007/10/02)
2-)Pyridin-2'-yl)phenylmercuric acetate has been prepared by mercuration of 2-phenylpyridine.Symmetrization of the corresponding chloride by alkaline sodium stannite gave bismercury, which was also prepared from 2-(2'-aminophenyl)pyridine by the diazo method and treatment of the initial product with copper powder and aqueous ammonia.Mercuration of benzoquinoline and 3,4,5-trimethyl-1-phenylpyrazole with mercuric acetate followed by treatment with lithium chloride yielded benzoquinolin-10-ylmercuric chloride and 2-(3',4',5'-trimethylpyrazol-1'-yl)phenylmercuric chloride respectively.Treatment of the former product with tribromide ions gave 10-bromobenzoquinoline.The exchange Grignard reaction between 1-phenylpyrazole and ethylmagnesium bromide to give 2-(pyrazol-1'-yl)phenylmagnesium bromide has been monitored by reactions with benzonitrile and D2O to establish optimum conditions for reaction with mercuric bromide giving bismercury.The 199Hg n.m.r. chemical shifts of the majority of mercurials are shifted substantially downfield to the corresponding simple phenylmercurials consistent with weak intramolecular coordination by the heterocyclic nitrogen donor atoms, but a small upfield shift is observed for bismercury.The X-ray crystal structure of bismercury 1/n, a 12.746(2), b 11.660(2), c 5.698(1) Angstroem, β 92.81(1) deg, V 845.8 Angstroem3> shows a centrosymmetric molecule with strong linear two coordination and significant but much weaker Hg-N interactions giving overall distorted square planar stereochemistry.The phenyl rings are mutually coplanar, whilst the two pyridin-2'-yl rings are parallel and inclined at 10.8 deg to the phenyl groups.
