By Alan R. Katritzky
Demonstrated in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of significant significance to natural chemists, polymer chemists, and so much organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry includes a cumulative topic index.
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27, 2478 (1962). 57 S. F. Mason, J . Ghem. SOC. 2071 (1954). 58 A. Albert and D. D. Perrin, unpublished results (1963). Sec. ] COVALENT HYDRATION : I. QUALITATIVE ASPECTS 33 ultraviolet spectrum and pK, value indicated that the 8-azapurine cation is hydrated. Ready oxidation with acidified hydrogen peroxide to 6-hydroxy-8-azapurine proved that the 1,6-double bond in 8-azapurine is the site of hydration. 2-Hydroxy-8-azapurine was shown by rapid-reaction techniques (see Section 11,E) t o be anhydrous in the anion and hydrated in the neutral species.
Soc. 4191 (1956). 37 A. Albert, Chem. SOC. (London) Spec. Publ. No. 3, 138 (1955). 38 D. J. Fry, J. D. Kendall, and A. J. Morgan, J . Chem. SOC. 6062 (1960). 36 Sec. 111. 21 COVALENT HYDRATION: I. 5 x (determined as described in the following review lo), but the derivatives have somewhat different values depending on the position and nature of the substituent. 8 x and 10 x respectively, indicating the electronattracting property of the nitro group. g. g. 13 Two important exceptions are now discussed.
05Mp-nitrophenylhydrazine made in a buffer of the same pH. l4*l5 Benzidine has also been used as a test reagent,24although the pH range in which it is effective is not wide. The kinetics for the reversible ring-opening of pteridine and its C-methyl derivatives have been studied in The electronic effects (S+ on carbon and S- on nitrogen) that favor the hydration of heteroaromatic molecules and of Schiff bases to give Dimroth bases are the same as those that would favor the ringopening of the hydrated heteroaromatic molecules and cleavage of the C-N bond in Dimroth compounds.