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Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano.A. Strecker, Liebigs Ann. Chem. 1861, 118, 151.T. Yamada, X. Liu, U. Englert, H. Yamane, R. Dronskowski, Chem. Eur. J. 2009, 15, 5651.

Guanidinium cation

Guanidine is protonated in physiological conditions. This conjugate acid is called the guanidinium cation, <sup>+</sup>. The guanidinium cation has a charge of +1. It is a highly stable cation in aqueous solution due to the efficient resonance stabilization of the charge and efficient solvation by water molecules. As a result, its pK<sub>a</sub> is 13.6Perrin, D.D., Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London, 1965; Supplement, 1972. meaning that guanidine is a very strong base in water.

<gallery>Image:Guanidinium-ion-3D-balls.png|<center>ball-and-stick model</center>Image:Guanidinium-ion-2D-skeletal.png|<center>resonance...
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