By Alan R. Katritzky
Demonstrated 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 includes a cumulative topic index.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 4
However, water is a much weaker nucleophilic reagent than most of the above substances and therefore would not remain strongly bound unless some further forces were operative. It is our belief that resonance is the principal cause of this extra stabilization. We have found that these resonances are varied in nature, but they all fit into one or the other of the following principal classes. 34 ADRIEN ALBERT AND w. L. [Sec. IV. F. ARMAREQO 1. Quinazoline,12the 1,3,~-triazanaphthalenes l 4(wherehydration is confined largely to the cation), and pteridine 6 , 24 (where the neutral species is hydrated to the extent of 22%) are examples of compounds in which stabilization of hydration by amidine resonance occurs.
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. Substituents in the 4-position, whether -I or +I,have a strong dehydrating effect (cf.
26 ADRIEN ALBERT AND w. L. F. ARMAREOO [Sec. 111. E. 24The spectrum of 17 at pH 2 changed steadily during 2-3 hr, but remained stable thereafter. This change (half-life 35 min) corresponded to the ring-opening reaction 17 + 18. The constitution of 18 was derived by spectral comparison with 2-aminomethyleneamino-3formylpyrazine oxime and its cation. 17. N H [181 The " blocking effect" of the methyl group in 4-methylpteridine has been found to decrease the ratio of the hydrated to the anhydrous species in the neutral molecule24and in the cation,44but the small proportion of hydrated cation rapidly undergoes the ring-opening reaction 4 4 19 +20 and hence is steadily regenerated from its anhydrous form.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky