Chemistry of Heterocyclic Compounds: s-Triazines and

Chapter I Cyanuric Acid and Derivatives (pages 17–146):
Chapter II Alkyl(Aryl)?s?Triazines (pages 147–184):
Chapter III Monohydroxy, Hydroxyamino, Dihydroxy?s??Triazines and similar Compounds (pages 185–216):
Chapter IV Monoamino? and Diamino?s??Triazines (pages 217–268):
Chapter V Ammelide, Ammeline and comparable Compounds (pages 269–308):
Chapter VI Melamine and Substituted Melamines (pages 309–388):
Chapter VII Isocyanuric Acid and Derivatives (pages 389–422):
Chapter VIII Condensed Ring s?Triazine platforms (pages 423–472):
Chapter IX Hexahydro?s?Triazines (pages 473–544):
Chapter X Hexamethylenetetramine (pages 545–596):
Chapter XI S?Triazaborane and Its Derivatives (pages 597–626):

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Extra info for Chemistry of Heterocyclic Compounds: s-Triazines and Derivatives, Volume 13

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98 H,NCOSCH,CONHC,H, A (111) K . Miscellaneous Preparations The following are brief descriptions of a few reactions which might be considered as minor or merely incidental preparations of cyanuric acid. Cyanuric acid is a stable chemical entity. It is frequently obtained as the terminal reaction product of drastic oxidations, in pyrolytic decompositions, or in synthetic work where there is opportunity for formation of the s-triazine nucleus or for hydrolysis of already existing substituted triazines.

Beyer, J. Am. Chem. ,76, 1948 (1954). 21. A. Hantzsch and H. , 38, 1010 (1905). 22. A. Weddige, J. prakt. , (2), 10, 212 (1874). 23. G. Lander, J. Chem. ,83, 411 (1903). 24. E. Bamberger and W. , 25, 534 (1892). 25. C. Grundmann, H. Ulrich and A. , 86, 181 (1953). 26. H. , 42, 803 (1909). 27. L. Hinkel, E. Ayling and J. Beynon, J. Chem. , 1935, 676. 28. E. , 29, 170 (1948) through C L m . Abst~acts,44, 9200 (1949). 29. L. Hinkel and T. Watkins, J . Claern. , 1940,407. 30. L. Hinkel and R. Dunn, J .

126Its relatively high absorbtivity in neutral or weakly basic solutions is indicative of resonance among such forms as: Recent ultraviolet absorption spectra s t u d i e ~ ' ~have ~ ' ~shown ~ the isocyanuric or tri-keto structure to exist in acidic solutions, below pH 6. 5, and the mono-keto structure above pH 11. No spectra of the fully ionized form were obtained even in 4 N sodium hydroxide solution. These ionizations may be represented by : H H 0 T y o HN . NH 'I0f 3 -7- 0TyoHN + N + HN Y N 0 pH-11 N N Y -Y 0 pH=6-8 -qp-- q j o 0- ( Cyanuric Acid and Derivatives 35 Hughes has shown128 lucidly that the crystalline structure of cyanuric acid supports the is0 or keto form.

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