By Alan R. Katritzky
Proven 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 features a cumulative topic index.
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Additional resources 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).
L. F. ARMAREOO [Sec. 111. 47The ultraviolet spectra do not reflect such a large constitutional change on ionization, and the subject needs further exploration. 7 The hydroxyl group is thought to be attached to C-7 and the negative charge to resonate between N-1 and N-3. The neutral species cannot be appreciably hydrated because its ultraviolet spectrum is very different from that of the anion. 4 and, hence, presumably, is hydrated. 48This is one of the few known examples where an anion is more hydrated than the corresponding neutral species,49because the ionizable hydrogen is derived from the water molecule that has been added.
Osborn, K. Schofield, and L. N. Short,J. 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.