Mercury(II) acetate

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Mercury(II) acetate
Mercury(II)-acetate-from-xtal-1973-2D.png
Mercury(II)-acetate-from-xtal-1973-3D-SF-A.png
Names
Other names
mercuric acetate
mercuriacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.993 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-766-2
PubChem CID
RTECS number
  • AI8575000
UNII
UN number 1629
  • InChI=1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 Yes check.svgY
    Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L Yes check.svgY
  • InChI=1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
    Key: BRMYZIKAHFEUFJ-NUQVWONBAS
  • ionic form:[Hg+2].[O-]C(=O)C.[O-]C(=O)C
  • coordination form:O=C(C)O[Hg]OC(C)=O
Properties
C4H6O4Hg
Molar mass 318.678 g/mol
Appearancewhite solid
Odor mild vinegar odor
Density 3.28 g/cm3, solid
Melting point 179 °C (354 °F; 452 K) (decomposes)
25 g/100 mL (10 °C)
100 g/100 mL (100 °C)
Solubility soluble in alcohol, diethyl ether
−100·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H300, H310, H330, H373, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Lethal dose or concentration (LD, LC):
40.9 mg/kg (rat, oral)
23.9 mg/kg (mouse, oral) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Mercury(II) acetate, also known as mercuric acetate is a chemical compound, the mercury(II) salt of acetic acid, with the formula Hg(O2 CCH3)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.

Contents

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. [2]

Synthesis and reactions

Mercury(II) acetate can be produced by reaction of mercuric oxide with acetic acid. [3]

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. [4] 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: [5]

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: [6]

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

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 dequamation (peeling and/or shedding of the skin). [7] Chronic exposure may cause reduced intelligence and kidney failure. [8]

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Aluminium chloride</span> Chemical compound

Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.

<span class="mw-page-title-main">Mercury sulfide</span> Chemical compound

Mercury sulfide, or mercury(II) sulfide is a chemical compound composed of the chemical elements mercury and sulfur. It is represented by the chemical formula HgS. It is virtually insoluble in water.

<span class="mw-page-title-main">Vinyl acetate</span> Chemical compound

Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers.

<span class="mw-page-title-main">Carbodiimide</span> Class of organic compounds with general structure RN=C=NR

In organic chemistry, a carbodiimide is a functional group with the formula RN=C=NR. On Earth they are exclusively synthetic, but in interstellar space the parent compound HN=C=NH has been detected by its maser emissions.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

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<span class="mw-page-title-main">Copper(II) acetate</span> Chemical compound

Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO− is acetate (CH
3CO−
2). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds. Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

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1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">Organomercury chemistry</span> Group of chemical compounds containing mercury

Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.

<span class="mw-page-title-main">Organolead chemistry</span>

Organolead chemistry is the scientific study of the synthesis and properties of organolead compounds, which are organometallic compounds containing a chemical bond between carbon and lead. The first organolead compound was hexaethyldilead (Pb2(C2H5)6), first synthesized in 1858. Sharing the same group with carbon, lead is tetravalent.

<span class="mw-page-title-main">Lead(IV) acetate</span> Organometallic compound (Pb(C2H3O2)4)

Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.

<span class="mw-page-title-main">Iodosobenzene</span> Chemical compound

Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula C6H5IO. This colourless solid compound is used as an oxo transfer reagent in research laboratories examining organic and coordination chemistry.

<span class="mw-page-title-main">Potassium hydrosulfide</span> Chemical compound

Potassium hydrosulfide is the inorganic compound with the formula KSH. This colourless salt consists of the cation K+ and the bisulfide anion [SH]−. It is the product of the half-neutralization of hydrogen sulfide with potassium hydroxide. The compound is used in the synthesis of some organosulfur compounds. Aqueous solutions of potassium sulfide consist of a mixture of potassium hydrosulfide and potassium hydroxide.

<span class="mw-page-title-main">Xylylene dibromide</span> Chemical compound

Xylylene dibromide is an organic compound with the formula C6H4(CH2Br)2. It is an off-white solid that, like other benzyl halides, a strong lachrymator. It is a useful reagent owing to the convenient reactivity of the two C-Br bonds. Two other isomers are known, para- and meta-xylylene dibromide.

References

  1. ↑ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Allmann, R. (1973). "Die Struktur des Quecksilber(II)-acetats". Zeitschrift für Kristallographie - Crystalline Materials. 138 (1–6): 366–373. doi: 10.1524/zkri.1973.138.jg.366 . S2CID   96160619.
  3. ↑ F. Wagenknecht; R. Juza (1963). "Mercury(II) Acetate". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY, NY: Academic Press. p. 1120.
  4. ↑ Newell, Lyman C.; Maxson, R. N.; Filson, M. H. (1939). "Red Mercuric Sulfide". Inorganic Syntheses. Vol. 1. pp. 19–20. doi:10.1002/9780470132326.ch7. ISBN   9780470132326.
  5. ↑ Whitmore, F. C.; Hanson, E. R. (1925). "o-Chloromercuriphenol". Organic Syntheses. 4: 13. doi:10.15227/orgsyn.004.0013.
  6. ↑ Carter, Herbert E.; West, Harold D. (1940). "DL-Serine". Organic Syntheses. 20: 81. doi:10.15227/orgsyn.020.0081.
  7. ↑ Bernhoft, Robin A. (2012). "Mercury Toxicity and Treatment: A Review of the Literature". Journal of Environmental and Public Health. 2012: 1–10. doi: 10.1155/2012/460508 . ISSN   1687-9805. PMC   3253456 . PMID   22235210.
  8. ↑ Bose-O'Reilly, Stephan; McCarty, Kathleen M.; Steckling, Nadine; Lettmeier, Beate (September 2010). "Mercury Exposure and Children's Health". Current Problems in Pediatric and Adolescent Health Care. 40 (8): 186–215. doi:10.1016/j.cppeds.2010.07.002. PMC   3096006 . PMID   20816346.
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