Tetrakis(acetoxymercuri)methane

Tetrakis(acetoxymercuri)methane
Names
	Other names Tetrakis(acetoxymercurio)methane
Identifiers
CAS Number	25201-30-3;
3D model (JSmol)	Interactive image;
ChemSpider	17615652;
PubChem CID	16683093;
UNII	VCG6X60HJW;
CompTox Dashboard (EPA)	DTXSID60179867 ;
	InChI InChI=1S/4C2H4O2.C.4Hg/c41-2(3)4;;;;;/h41H3,(H,3,4);;;;;/q;;;;;4*+1/p-4 Key: FUFKDCOYEVSHMN-UHFFFAOYSA-J;
	SMILES CC(=O)O[Hg]C([Hg]OC(=O)C)([Hg]OC(=O)C)[Hg]OC(=O)C;
Properties
Chemical formula	C9H12Hg4O8
Molar mass	1050.555 g·mol−1
Appearance	white solid
Density	3.71 g/cm3
Melting point	265–285 °C (509–545 °F; 538–558 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetrakis(acetoxymercuri)methane is an organomercury compound with the formula formula C(HgO₂CCH₃)₄.^[2] It was obtained in the investigation of Hofmann's base, an ill-defined yellowish material produced by treatment of mercuric oxide with base in ethanol.^[3] Hofmann's base was once thought to have the formula C₂Hg₆(OH)₂. Eventually it was found to dissolve in carboxylic acids (RCO₂H) to give colorless derivatives of the type C(HgO₂CR)₄. Several tetramercurimethane derivatives have now been characterized by X-ray crystallography.^[4]^[5]

Independent of studies on Hofmann's base, tetrakis(acetoxymercuri)methane was first prepared by reaction of the tetraborylmethane C(B(OCH₃)₂)₄ with mercuric acetate.^[1]

References

^ ^a ^b Matteson, Donald S.; Castle, Richard B.; Larson, Gerald L. (1970). "Tetrakis(acetoxymercuri)methane". Journal of the American Chemical Society. 92 (1): 231–232. Bibcode:1970JAChS..92..231M. doi:10.1021/ja00704a055.
^ Milic, Dalibor; Soldin, Zeljka; Giester, Gerald; Popovic, Zora; Matkovic-Calogovic, Dubravka (2009). "Crystal Structure of the First Polymeric Tetramercurated Methane Derivative of Hofmann's Base". Croatica Chemica Acta. 82: 337-344.
^ K. A. Hofmann (1898). "Ueber Oxymercarbide". Chemische Berichte. 31page=1904-1909 (2): 1904–1909. doi:10.1002/cber.189803102117.
^ Grdenić, Drago; Kamenar, Boris; Korpar-Čolig, Branka; Sikirca, Milan; Jovanovski, Gligor (1974). "Tetrakis(trifluoroacetoxymercuri)methane and Tetrakis(acetoxymercuri)methane as the Reaction Products of Hofmann's Base with the Corresponding Acid: X-ray Crystallographic Evidence". J. Chem. Soc., Chem. Commun. (16): 646–647. doi:10.1039/C39740000646.
^ Grdenić, Drago; Korpar-Čolig, Branka; Matković-Čalogovíć, Dubravka (1996). "Synthesis and crystal structures of tetrakis(nitratomercurio) methane monohydrate and bis(sulphatomercurio)bis(aquamercurio) methane". Journal of Organometallic Chemistry. 522 (2): 297–302. doi:10.1016/0022-328X(96)06302-4.

[DSM-1] Matteson, Donald S.; Castle, Richard B.; Larson, Gerald L. (1970). "Tetrakis(acetoxymercuri)methane". Journal of the American Chemical Society. 92 (1): 231–232. Bibcode:1970JAChS..92..231M. doi:10.1021/ja00704a055.

[2] Milic, Dalibor; Soldin, Zeljka; Giester, Gerald; Popovic, Zora; Matkovic-Calogovic, Dubravka (2009). "Crystal Structure of the First Polymeric Tetramercurated Methane Derivative of Hofmann's Base". Croatica Chemica Acta. 82: 337-344.

[3] K. A. Hofmann (1898). "Ueber Oxymercarbide". Chemische Berichte. 31page=1904-1909 (2): 1904–1909. doi:10.1002/cber.189803102117.

[4] Grdenić, Drago; Kamenar, Boris; Korpar-Čolig, Branka; Sikirca, Milan; Jovanovski, Gligor (1974). "Tetrakis(trifluoroacetoxymercuri)methane and Tetrakis(acetoxymercuri)methane as the Reaction Products of Hofmann's Base with the Corresponding Acid: X-ray Crystallographic Evidence". J. Chem. Soc., Chem. Commun. (16): 646–647. doi:10.1039/C39740000646.

[5] Grdenić, Drago; Korpar-Čolig, Branka; Matković-Čalogovíć, Dubravka (1996). "Synthesis and crystal structures of tetrakis(nitratomercurio) methane monohydrate and bis(sulphatomercurio)bis(aquamercurio) methane". Journal of Organometallic Chemistry. 522 (2): 297–302. doi:10.1016/0022-328X(96)06302-4.

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