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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 444008175 |
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|Watchedfields = changed |
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| Name = Mercury(II) acetate |
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|verifiedrevid = 444009303 |
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| ImageFile1 = Mercury(II)-acetate-from-xtal-1973-2D.png |
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|Name = Mercury(II) acetate |
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| ImageSize1 = 256px |
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| ImageFile2 = Mercury(II)-acetate-from-xtal-1973-3D-balls-A.png |
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|ImageFile1 = Mercury(II)-acetate-from-xtal-1973-2D.png |
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|ImageSize1 = 256px |
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| ImageFile3 = Mercury(II)-acetate-from-xtal-1973-3D-SF-A.png |
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|ImageFile2 = |
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| ImageName = Mercury(II) acetate |
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|ImageFile3 = Mercury(II)-acetate-from-xtal-1973-3D-SF-A.png |
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| OtherNames = mercuric acetate<br /> mercuriacetate |
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|ImageName = Mercury(II) acetate |
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| Section1 = {{Chembox Identifiers |
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|OtherNames = mercuric acetate<br /> mercuriacetate<br /> mercury diacetate |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 14599 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 14599 |
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| UNII = R0G1MCT8Y5 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 |
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|UNII = R0G1MCT8Y5 |
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| InChIKey = BRMYZIKAHFEUFJ-NUQVWONBAS |
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|InChI = 1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|InChIKey = BRMYZIKAHFEUFJ-NUQVWONBAS |
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| ChEBI = 33211 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = .C(=O)C.C(=O)C |
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|ChEBI = 33211 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|EC_number = 209-766-2 |
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| StdInChI = 1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 |
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|RTECS = AI8575000 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|UNNumber = 1629 |
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| StdInChIKey = BRMYZIKAHFEUFJ-UHFFFAOYSA-L |
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|SMILES = .C(=O)C.C(=O)C |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|SMILES_Comment = ionic form |
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| CASNo = 1600-27-7 |
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|SMILES1 = O=C(C)OOC(C)=O |
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}} |
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|SMILES1_Comment = coordination form |
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| Section2 = {{Chembox Properties |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>4</sub>Hg |
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|StdInChI = 1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 |
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| MolarMass = 318.70 g/mol |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Appearance = white crystals |
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|StdInChIKey = BRMYZIKAHFEUFJ-UHFFFAOYSA-L |
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| Density = 3.27 g/cm³, solid |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Solubility = 25 g/100 mL (10°C) |
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|CASNo = 1600-27-7 |
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| SolubleOther = soluble in ] |
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|PubChem = 15337 |
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| MeltingPt = 179°C (decomposes) |
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| BoilingPt = |
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}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = |
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| NFPA-H = 3 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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'''Mercury(II) acetate''' is the ] with the ] ](]]C])<sub>2</sub>. Commonly abbreviated Hg(OAc)<sub>2</sub>, this compound is employed as a reagent to generate ] compounds from unsaturated organic precursors. |
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|Formula = C<sub>4</sub>H<sub>6</sub>O<sub>4</sub>Hg |
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|MolarMass = 318.678 g/mol |
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|Appearance = white solid |
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|Odor = mild ] odor |
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|Density = 3.28 g/cm<sup>3</sup>, solid |
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|Solubility = 25 g/100 mL (10 °C) <br> 100 g/100 mL (100 °C) |
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|SolubleOther = soluble in ], ] |
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|MeltingPtC = 179 |
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|MeltingPt_notes = (decomposes) |
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| MagSus = −100·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section7={{Chembox Hazards |
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|NFPA-H = 4 |
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|NFPA-F = 0 |
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|NFPA-R = 0 |
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|LD50 = 40.9 mg/kg (rat, oral)<br/>23.9 mg/kg (mouse, oral)<ref>{{IDLH|merc-hg|Mercury (organo) alkyl compounds (as Hg)}}</ref> |
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|GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|300|310|330|373|410}} |
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|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}} |
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}} |
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'''Mercury(II) acetate''', also known as '''mercuric acetate''' is a ], the mercury(II) salt of acetic acid, with the ] ](]]C])<sub>2</sub>. Commonly abbreviated Hg(OAc)<sub>2</sub>, this compound is employed as a reagent to generate ] compounds from unsaturated organic precursors. It is a white, water-soluble solid, but some samples can appear yellowish with time owing to decomposition. |
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==Structure== |
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==Structure== |
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Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)<sub>2</sub> 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.<ref>{{ cite journal | author = R. Allmann | journal = Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem. | year = 1973 | volume = 138 | pages = 366–373 }}</ref> |
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Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)<sub>2</sub> molecules with Hg-O distances of 2.07]. 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.<ref>{{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 }}</ref> |
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<!-- unlikely any reader really cares<center>] ]</center>--> |
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==Synthesis and reactions== |
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<center>] ]</center> |
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Mercury(II) acetate can be produced by reaction of ] with ].<ref>{{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}}</ref> |
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HgO + 2 CH<sub>3</sub>COOH → Hg(CH<sub>3</sub>COO)<sub>2</sub> + ] |
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==Reactions== |
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]s undergo "mercuration" upon treatment with Hg(OAc)<sub>2</sub>. The one acetate group that remains on mercury can be displaced by chloride:<ref> Whitmore, F. C.; Hanson, E. R. "o-Chloromercuriphenol" Organic Syntheses, Collected Volume 1, p.161 (1941).http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0161</ref> |
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:C<sub>6</sub>H<sub>5</sub>OH + Hg(OAc)<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(OH)-2-HgOAc + ] |
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:C<sub>6</sub>H<sub>4</sub>(OH)-2-HgOAc + NaCl → C<sub>6</sub>H<sub>4</sub>(OH)-2-HgCl + NaOAc |
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===Inorganic reactions=== |
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The Hg<sup>2+</sup> center binds to ]s, inducing the addition of ] and ]. For example, treatment of methyl] with mercuric acetate in ] gives an α-mercuri ester:<ref>Carter, H. E.; West, H. D. “dl-Serine” Organic Syntheses, Collected Volume 3, p.774 (1955). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0774</ref> |
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Mercury(II) acetate in acetic acid solution reacts with ] to rapidly precipitate the black (β) ] of ]. With gentle heating of the slurry, the black solid converts to the red form.<ref>{{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 }}</ref> The mineral ] is red HgS. The precipitation of HgS as well as a few other sulfides, using hydrogen sulfide is a step in ]. |
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:Hg(OAc)<sub>2</sub> + CH<sub>2</sub>=CHCO<sub>2</sub>CH<sub>3</sub> + ] → CH<sub>3</sub>OCH<sub>2</sub>CH(HgOAc)CO<sub>2</sub>CH<sub>3</sub> + HOAc |
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===Organic chemistry=== |
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Mercury(II) has a high affinity for sulfur ligands. Hg(OAc)<sub>2</sub> can be used as a ] to remove the acetamidomethyl ], which is used to "protect" thiol groups in ]. Similarly Hg(OAc)<sub>2</sub> is a standard reagent to convert ] esters into dithiocarbonates: |
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Electron-rich ]s undergo "mercuration" upon treatment with Hg(OAc)<sub>2</sub>. This behavior is illustrated with ]: |
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:(RS)<sub>2</sub>C=S + H<sub>2</sub>O + Hg(OAc)<sub>2</sub> → (RS)<sub>2</sub>C=O + ] + 2 HOAc |
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:C<sub>6</sub>H<sub>5</sub>OH + Hg(OAc)<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(OH)-2-HgOAc + HOAc |
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The acetate group (OAc) that remains on mercury can be displaced by chloride:<ref>{{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}}</ref> |
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:C<sub>6</sub>H<sub>4</sub>(OH)-2-HgOAc + NaCl → C<sub>6</sub>H<sub>4</sub>(OH)-2-HgCl + NaOAc |
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The Hg<sup>2+</sup> center binds to ]s, inducing the addition of ] and ]. For example, treatment of ] with mercuric acetate in ] gives an α-mercuri ester:<ref>{{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}}</ref> |
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:Hg(OAc)<sub>2</sub> + CH<sub>2</sub>=CHCO<sub>2</sub>CH<sub>3</sub> + ] → CH<sub>3</sub>OCH<sub>2</sub>CH(HgOAc)CO<sub>2</sub>CH<sub>3</sub> + HOAc |
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Exploiting the high affinity of mercury(II) for sulfur ligands, Hg(OAc)<sub>2</sub> can be used as a ] to ] thiol groups in ]. Similarly Hg(OAc)<sub>2</sub> has been used to convert ] esters into dithiocarbonates: |
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:(RS)<sub>2</sub>C=S + H<sub>2</sub>O + Hg(OAc)<sub>2</sub> → (RS)<sub>2</sub>C=O + ] + 2 HOAc |
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Mercury(II) acetate is used for ] reactions. |
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A famous use of Hg(OAc)<sub>2</sub> was in the synthesis of ]. |
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== Toxicity == |
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{{main|Mercury poisoning}} |
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Mercuric acetate is a highly toxic compound, due to it being water-soluble and having mercury ions. |
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Symptoms of mercury poisoning include ], skin discoloration and ] (peeling and/or shedding of the skin).<ref>{{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 }}</ref> Chronic exposure may cause reduced intelligence and ].<ref>{{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}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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] |
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] |
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{{Mercury compounds}} |
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{{Mercury compounds}} |
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{{clear}} |
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{{inorganic-compound-stub}} |
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{{Acetates}} |
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