By Alan R. Katritzky

Validated in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of significant value to natural chemists, polymer chemists, and so much organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry features a cumulative topic index.

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O The amount of the hydrated form in the anions is always smaller than in the neutral species, but it is not always negligible. Thus, the percentages in 2-hydroxy-, 2-hydroxy-6-methyl-, 2-mercapto-, and 2,6-dihydroxypteridine are 12, 9, 19, and 36%,46respectively (see also Table V I in ref. 10). Many pteridines which, in the anhydrous form, lack an ionizable hydrogen atoin give stable anions clearly indicating that hydration of the neutral species must precede formation of anions. The various N-alkyl derivatives of 2- and 6-hydroxypteridine behave in this way.

Am. C h m . SOC. 52, 2846 (1930). 33 A. Albert, J . Chm. 1790 (1960). 28aT. 29 Sec. 111. ] COVALENT HYDRATION: I. QUALITATIVE ASPECTS 19 l,%napththyridine. The principal evidence against hydration was the similarity between the ultraviolet spectra measured in cyclohexane, in water at near neutral pH, and in dilute aqueous acid. The ionization constants also showed no apparent anomaly. 2o The relatively positive nature (see Section IV) of C-2 and C-5 seems to be responsible for the absence of hydration.

SOC. 53, 245 (1931). 32 F. W. Bergstrom and S. H. McAllister, J . Am. C h m . SOC. 52, 2846 (1930). 33 A. Albert, J . Chm. 1790 (1960). 28aT. 29 Sec. 111. ] COVALENT HYDRATION: I. QUALITATIVE ASPECTS 19 l,%napththyridine. The principal evidence against hydration was the similarity between the ultraviolet spectra measured in cyclohexane, in water at near neutral pH, and in dilute aqueous acid. The ionization constants also showed no apparent anomaly. 2o The relatively positive nature (see Section IV) of C-2 and C-5 seems to be responsible for the absence of hydration.

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Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky
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