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GUANIDINE, CN3H5

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Originally appearing in Volume V12, Page 651 of the 1911 Encyclopedia Britannica.
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GUANIDINE, CN3H5 or HN: C(See also:NH2)2, the amidine of amidocarbonic See also:acid. It occurs in See also:beet juice. It was first prepared in 1861 by A. Strecker, who oxidized guanine with hydrochloric acid and See also:potassium chlorate. It may be obtained synthetically by the See also:action of ammonium iodide on See also:cyanamide, CN•NH2+ NI14I=CN3H5•HI•; by See also:heating ortho-carbonic See also:esters with See also:ammonia toso° C.; but best by heating ammonium thiocyanate to 18o°-190° C., when the thiourea first formed is converted into guanidine thiocyanate, 2CS(NH2)2=HN: C(NH2)2•HCNS+H2S. It is a colourless crystalline solid, readily soluble in See also:water and See also:alcohol; it deliquesces on exposure to See also:air. It has strong basic properties, absorbs See also:carbon dioxide readily, and forms well-defined crystalline salts. Baryta water hydrolyses it to See also:urea. By See also:direct See also:union with glycocoll acid, it yields glycocyamine, NH2•(HN): C•NH•See also:CH2See also:CO2H, whilst with methyl glycocoll (sarcosine) it forms creatine, NH2•(NH): C•N(See also:CH3)•CH2•CO2H. Many derivatives of guanidine were obtained by J. Thiele (See also:Ann., 1892, 270, p. I ; 1893, 273, p.

133; Ber., 1893, 26, pp. 2598, 2645). By the action of nitric acid on guanidine in the presence of sulphuric acid, nitroguanidine, HN:C(NH2)•NH.NO2 (a substance possessing acid properties) is obtained; from which, by reduction with See also:

zinc dust, amidoguanidine, HN:C(NH2)•NH•NH2, is formed. This amidoguanidine decomposes on See also:hydrolysis with the formation of semicarbazide, NH2•CO•NH•NH2, which, in its turn, breaks down into carbon dioxide, ammonia and See also:hydrazine. Amidoguanidine is a See also:body of hydrazine type, for it reduces See also:gold and See also:silver salts and yields a benzylidine derivative. On oxidation with potassium permanganate, it gives azodicarbondiamidine nitrate, NH2• (HN) : C.N: N•C:(NH)•NH2.2HNO3, which,when reduced by sulphuretted See also:hydrogen, is converted into the corresponding hydrazodicarbondiamidine, NH2•(HN):C•NH•NH•C:(NH)•NH2. By the action of nitrous acid on a nitric acid See also:solution of amidoguanidine, diazoguanidine nitrate, NH2•(HN):C•NH•N2•NO3, is obtained. This diazo See also:compound is decomposed by See also:caustic alkalis with the formation of cyanamide and hydrazoic acid, CH4N5•NO3=N3Hd-CN•NH2+ HNO3, whilst acetates and See also:carbonates convert it into amidotetra- N—N. zotic acid, See also:H2N•C II . Amidotetrazotic acid yields addition \NH—N compounds with See also:amines, and by the further action of nitrous acid yields a very explosive derivative, diazotetrazol, CN6. By fusing guanidine with urea, dicyandiamidineH2N•(HN):C•NH•CO•NH2,is formed.

End of Article: GUANIDINE, CN3H5

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