Mercury cyanates

Scholl and co-workers reported that mercury cyanate (fulminate) and HCI reacts with benzene in the presence of AICI3 to give benzaldoxime and benzonitrile, whereas the aldoxime of resorcinol and by-product dioxybenzonitrile is produced from the same reagents but in the absence of AICI3 (Eq 1.20). 

Both structures II and III have an arrangement of atoms that places a positive formal charge on atoms that are higher in electronegativity than carbon. Consequently, the most stable arrangement of atoms is as shown in structure I. Some compounds containing the ion having structure III (the fulminate ion) are known, but they are much less stable than the cyanates (structure I). In fact, mercury fulminate has been used as a detonator. 

Chandelon Also spelled Chandelen. A process for making mercuric cyanate, (mercury fulminate) by dissolving mercuiy in nitric acid and pouring the solution into aqueous ethanol. Developed by Chandelon in Belgium in 1848. 

Mercury(II) cyanate, 0977 Mercury(II) cyanide, 0976 Mercury(II) ac/-dinitrometbanide, 0707 Mercury(l) fluoride, 4312 Mercury(ll) formohydroxamate, 0804 Mercury(ll) fubninate, 0978 Mercury(1) hypophosphate, 4617 Mercury(ll) iodide, 4602 Mercury(l) nitrate, 4609 Mercury(ll) nitrate, 4603... 

Aromatic hydrocarbons (including benzene), phenols, and phenolic ethers can be cyanated with trichloroacetonitrile, BrCN, or mercury fulminate Hg(ONC)2.36 In the case of CljCCN,... 

Mercury(II) cyanate is formed from AgNCO and HgCl2 in methanol.51 The potassium salt... 

Sodium cyanide solution dissolves certain metals (I) with absorption of oxygen, e.g.. gold, silver, mercury, lead, and (2) with evolution of hydrogen, e.g.. copper, nickel, iron. zinc, aluminum, magnesium and solid sodium cyanide, when heated with certain oxides, e.g.. lead monoxide PhO. stannic oxide SnO.. yields the metal of the oxide, e.g.. lead. tin. respectively. and sodium cyanate NaCNO. Two classes of esters arc known, cyanides or nitriles, and isocyanides, isonitriles or carbylatnincs. the latter being very poisonous and of marked nauseating odor... 

The cyanide and cyanate are salts of weak acids and are largely hydrolyzed, and the solution, if it is titrated immediately, appears to have developed four molecules of sodium hydroxide for every molecule of mercury in the sample which was taken. If the solution is allowed to stand, the alkalinity gradually decreases because of a secondary reaction whereby sulfate and thiocyanate are formed. 

Mercury(II) acetylide, 0971 Mercury(II) amide chloride, 3993 Mercury(II) azide, 4599 Mercury(II) bromate, 0269 Mercury(II) bromide, 0268 Mercury(II) chloride, 4070 Mercury(II) chlorite, 4071 Mercury(II) cyanate, 0973 Mercury(II) cyanide, 0972 Mercury(II) a -dinitromethanide, 0703 Mercury(II) formohydroxamate, 0800 Mercury(II) fulminate, 0974 Mercury(II) iodide, 4597 Mercury(II) nitrate, 4598 Mercury(II) 5-nitrotetrazolide, 0977 Mercury(II) oxalate, 0978 Mercury(II) oxide, 4600... 

See Mercury(II) cyanate, Potassium cyanate, Silver cyanate See also FULMINATING METALS... 

Fulminate of mercury Mercuric cyanate HG[Pg.556]

IV.9 CYANATES, OCN- Solubility The cyanates of the alkalis and of the alkaline earths are soluble in water. Those of silver, mercury(I), lead, and copper are insoluble. The free acid is a colourless liquid with an unpleasant odour it is very unstable. 

The identification of isomers i and ii is made on the basis of NMR data (170). Only isomer i undergoes further chlorine elimination in the presence of mercury to afford the desired product in 10% yield. Isomer ii under similar conditions decomposes to give SOF4 and C1CN. The IR and 14N NMR spectra (170, 172) are used to differentiate between SF5 cyanate and SF5 isocyanate. 

DOT CLASSIFICATION 6.1 Label Poison SAFETY PROFILE A poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. Thermally unstable and decomposition may be vigorous. When heated to decomposition it emits very toxic fumes of Hg, NOx, SOx, and CN". See also MERCURY COMPOUNDS and CYANATES. 

Mercury fulminate. Mercury fulminate or mercuric cyanate, 10, is a grey-white powder obtained by reacting mercuric nitrate with alcohol in nitric acid... 

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