Mercury(II) acetate
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 444009303
|Name = Mercury(II) acetate
|ImageFile1 = Mercury(II)-acetate-from-xtal-1973-2D.png
|ImageSize1 = 256px
|ImageFile2 =
|ImageFile3 = Mercury(II)-acetate-from-xtal-1973-3D-SF-A.png
|ImageName = Mercury(II) acetate
|OtherNames = mercuric acetate
mercuriacetate
mercury diacetate
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 14599
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = R0G1MCT8Y5
|InChI = 1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
|InChIKey = BRMYZIKAHFEUFJ-NUQVWONBAS
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 33211
|EC_number = 209-766-2
|RTECS = AI8575000
|UNNumber = 1629
|SMILES = [Hg+2].[O-]C(=O)C.[O-]C(=O)C
|SMILES_Comment = ionic form
|SMILES1 = O=C(C)O[Hg]OC(C)=O
|SMILES1_Comment = coordination form
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = BRMYZIKAHFEUFJ-UHFFFAOYSA-L
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 1600-27-7
|PubChem = 15337
}}
|Section2={{Chembox Properties
|Formula = C4H6O4Hg
|MolarMass = 318.678 g/mol
|Appearance = white solid
|Odor = mild vinegar odor
|Density = 3.28 g/cm3, solid
|Solubility = 25 g/100 mL (10 °C)
100 g/100 mL (100 °C)
|SolubleOther = soluble in alcohol, diethyl ether
|MeltingPtC = 179
|MeltingPt_notes = (decomposes)
| MagSus = −100·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
|NFPA-H = 4
|NFPA-F = 0
|NFPA-R = 0
|LD50 = 40.9 mg/kg (rat, oral)
23.9 mg/kg (mouse, oral){{IDLH|merc-hg|Mercury (organo) alkyl compounds (as Hg)}}
|GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|300|310|330|373|410}}
|PPhrases = {{P-phrases|260|262|264|270|271|273|280|284|301+310|302+350|304+340|310|314|320|321|322|330|361|363|391|403+233|405|501}}
}}
}}
Mercury(II) acetate, also known as mercuric acetate is a chemical compound, the mercury(II) salt of acetic acid, with the formula Hg(O2CCH3)2. Commonly abbreviated Hg(OAc)2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors. It is a white, water-soluble solid, but some samples can appear yellowish with time owing to decomposition.
Structure
Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)2 molecules with Hg-O distances of 2.07 Å. Three long, weak intermolecular Hg···O bonds of about 2.75 Å are also present, resulting in a slightly distorted square pyramidal coordination geometry at Hg.{{cite journal | author = Allmann |first=R. | journal = Zeitschrift für Kristallographie - Crystalline Materials|title=Die Struktur des Quecksilber(II)-acetats | year = 1973 | volume = 138 |issue=1–6 | pages = 366–373 |doi=10.1524/zkri.1973.138.jg.366|s2cid=96160619 |doi-access=free }}
Synthesis and reactions
Mercury(II) acetate can be produced by reaction of mercuric oxide with acetic acid.{{cite book|author1=F. Wagenknecht|author2=R. Juza|chapter=Mercury(II) Acetate|title=Handbook of Preparative Inorganic Chemistry, 2nd Ed. |editor=G. Brauer|publisher=Academic Press|year=1963|place=NY, NY|volume=2|pages=1120}}
HgO + 2 CH3COOH → Hg(CH3COO)2 + H2O
=Inorganic reactions=
Mercury(II) acetate in acetic acid solution reacts with H2S to rapidly precipitate the black (β) polymorph of HgS. With gentle heating of the slurry, the black solid converts to the red form.{{cite book |doi=10.1002/9780470132326.ch7|chapter=Red Mercuric Sulfide|year=1939|last1=Newell|first1=Lyman C.|last2=Maxson|first2=R. N.|last3=Filson|first3=M. H.|title=Inorganic Syntheses |pages=19–20|volume=1|isbn=9780470132326 }} The mineral cinnabar is red HgS. The precipitation of HgS as well as a few other sulfides, using hydrogen sulfide is a step in qualitative inorganic analysis.
=Organic chemistry=
Electron-rich arenes undergo "mercuration" upon treatment with Hg(OAc)2. This behavior is illustrated with phenol:
:C6H5OH + Hg(OAc)2 → C6H4(OH)-2-HgOAc + HOAc
The acetate group (OAc) that remains on mercury can be displaced by chloride:{{cite journal |doi=10.15227/orgsyn.004.0013|first1=F. C.|last1=Whitmore|first2=E. R.|last2=Hanson|title=o-Chloromercuriphenol|journal=Organic Syntheses|volume=4|pages=13|year=1925}}
:C6H4(OH)-2-HgOAc + NaCl → C6H4(OH)-2-HgCl + NaOAc
The Hg2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methyl acrylate with mercuric acetate in methanol gives an α-mercuri ester:{{cite journal |first1=Herbert E. |last1=Carter|first2=Harold D.|last2= West|doi=10.15227/orgsyn.020.0081|title=DL-Serine|journal=Organic Syntheses|volume=20|pages=81|year=1940}}
:Hg(OAc)2 + CH2=CHCO2CH3 + CH3OH → CH3OCH2CH(HgOAc)CO2CH3 + HOAc
Exploiting the high affinity of mercury(II) for sulfur ligands, Hg(OAc)2 can be used as a reagent to deprotect thiol groups in organic synthesis. Similarly Hg(OAc)2 has been used to convert thiocarbonate esters into dithiocarbonates:
:(RS)2C=S + H2O + Hg(OAc)2 → (RS)2C=O + HgS + 2 HOAc
Mercury(II) acetate is used for oxymercuration reactions.
A famous use of Hg(OAc)2 was in the synthesis of idoxuridine.
Toxicity
{{main|Mercury poisoning}}
Mercuric acetate is a highly toxic compound, due to it being water-soluble and having mercury ions.
Symptoms of mercury poisoning include peripheral neuropathy, skin discoloration and desquamation (peeling and/or shedding of the skin).{{Cite journal |last=Bernhoft |first=Robin A. |date=2012 |title=Mercury Toxicity and Treatment: A Review of the Literature |journal=Journal of Environmental and Public Health |language=en |volume=2012 |pages=1–10 |doi=10.1155/2012/460508 |issn=1687-9805 |pmc=3253456 |pmid=22235210 |doi-access=free }} Chronic exposure may cause reduced intelligence and kidney failure.{{Cite journal |last1=Bose-O'Reilly |first1=Stephan |last2=McCarty |first2=Kathleen M. |last3=Steckling |first3=Nadine |last4=Lettmeier |first4=Beate |date=September 2010 |title=Mercury Exposure and Children's Health |journal=Current Problems in Pediatric and Adolescent Health Care |language=en |volume=40 |issue=8 |pages=186–215 |doi=10.1016/j.cppeds.2010.07.002 |pmc=3096006 |pmid=20816346}}
References
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{{Mercury compounds}}
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{{Acetates}}