Editing Dimethylmercury (section)

==Synthesis, structure, and reactions==
The compound was one of the earliest [[organometallic]]s reported, reflecting its considerable stability.  The compound was first prepared by [[George Bowdler Buckton|George Buckton]] in 1857 by a reaction of [[methylmercury]] [[iodide]] with [[potassium cyanide]]:<ref name=":0">{{Cite book|title=The Chemistry of mercury|date=1977|publisher=Macmillan|editor-last=McAuliffe|editor-first=C. A.|isbn=978-1-349-02489-6|location=London|oclc=1057702183}}{{page needed|date=January 2025}}</ref>
: 2 CH<sub>3</sub>HgI + 2 KCN → Hg(CH<sub>3</sub>)<sub>2</sub> + 2 KI + (CN)<sub>2</sub> + Hg
Later, [[Edward Frankland]] discovered that it could be synthesized by treating [[sodium amalgam]] with [[methyl]] [[halide]]s:
: Hg + 2 Na + 2 [[Methyl iodide|CH<sub>3</sub>I]] → Hg(CH<sub>3</sub>)<sub>2</sub> + 2 [[Sodium iodide|NaI]]
It can also be obtained by [[alkylation]] of [[Mercury(II) chloride|mercuric chloride]] with [[methyllithium]]:
: HgCl<sub>2</sub> + 2 LiCH<sub>3</sub> → Hg(CH<sub>3</sub>)<sub>2</sub> + 2 [[Lithium chloride|LiCl]]
The molecule adopts a linear structure with Hg–C bond lengths of 2.083&nbsp;Å.<ref>{{cite book |last1=Holleman |first1=A. F. |last2=Wiberg |first2=Egon |last3=Wiberg |first3=Nils |title=Inorganic Chemistry |publisher=Academic Press |location=San Diego |year=2001 |isbn=0-12-352651-5}}</ref>

===Reactivity and physical properties===
Dimethylmercury is stable in water and reacts with mineral acids at a significant rate only at elevated temperatures,<ref>{{cite book |title=The Organometallic Chemistry of the Transition Metals |last=Crabtree |first=Robert H. |author-link=Robert H. Crabtree |year=2005 |publisher=John Wiley |isbn=0471662569 |edition= 4th |location=Hoboken, N.J. |pages=424 |oclc=61520528}}</ref><ref>{{cite book |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=9100TLU0.TXT |title=Chemistry of Organomercurials in Aquatic Systems |last1=Baughman |first1=George L. |first2=John A. |last2=Gordon |first3=N. Lee |last3=Wolfe |first4=Richard G. |last4=Zepp |publisher=[[U.S. Govt. Print. Off.]] |date=September 1973 |pages=34–40 |series=[[United States Environmental Protection Agency]] Ecological Research Series |access-date=2021-01-29}}</ref> whereas the corresponding [[organocadmium]] and [[organozinc]] compounds (and most metal alkyls in general) hydrolyze rapidly. The difference reflects the high [[electronegativity]] of Hg (Pauling EN = 2.00) and the low affinity of Hg(II) for oxygen ligands. The compound undergoes a [[Redistribution (chemistry)|redistribution reaction]] with mercuric chloride to give methylmercury chloride:
: (CH<sub>3</sub>)<sub>2</sub>Hg  +  HgCl<sub>2</sub>  →   2 CH<sub>3</sub>HgCl
Whereas dimethylmercury is a [[volatile liquids|volatile liquid]], [[methylmercury|methylmercury chloride]] is a [[crystalline solid]].<ref>{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Methylmercuric_chloride#section=Top |title=Methylmercury chloride |website=[[PubChem]] |publisher=[[National Center for Biotechnology Information]], United States [[National Institutes of Health]] |access-date=2021-01-29}}</ref>