By Alan R. Katritzky
Verified in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of significant significance to natural chemists, polymer chemists, and such a lot organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry encompasses a cumulative topic index.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 4
Confirmation of the positions of hydration was obtained by use of the (‘blocking effect ” of a methyl group in the 4- and 7positions, respectively. 46 By analogy with this, other hydroxypteridines which are hydrated to some extent in the neutral species would be expected to have a still higher proportion of the hydrated species in the cation. However, because of the low basic pK, values of 2-hydroxypteridine and its derivatives, the acid required for protonation is apparently strong enough to have a dehydrating effect (see Section 11,B, 2).
The gwnidine-type resonance, which is present in aliphatic guanidines, is stronger than that in the corresponding amidines, at least in the case of the cationic forms. 2-Aminopteridine21 and 2-aminoquinazoline cations 39 are two examples of compounds in which hydration is stabilized by the presence of a guanidino group (32). 3. The urea-type resonance is illustrated, as the neutral species, by 33. Resonance of this type does not operate in anionic species because one of the two possible canonical forms would have to carry the negative charge on the oxygen atom and the other on the nitrogen atom, and these forms would be unequivalent.
61, 2044 (1928). 30 F. Krohnke and H. Honig, Ann. C h m . 624,97 (1959). 31 F. W. Bergstrom and R. A. Ogg, J . Am. C h m . 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.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky