By Alan R. Katritzky
Tested 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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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.
11 COVALENT HYDRATION: I. QUALITATIVE ASPECTS 23 higher acidities which are necessary (because of the lower pK, values) to protonate the N-oxide molecules have a dehydrating effect. l6 D. TRIAZANAPHTHALENES 1. 1,3,~-Triazanaphthulenes These compounds are discussed in two separate groups: (a)the 1,2,3- and 1,2,4-triazanaphthalenes,and ( b ) the 1,3,5-, 1,3,6-, 1,3,7-, and 1,3,8-triazanaphthalenes. (a)1,2,3-Triazanaphthalene has not been prepared but several observations 41 suggest that it would behave as an unstable diazonium compound.
A. Albert and G . B. Barlin, J . C h m . 5737 (1963). Sec. ] COVALENT HYDRATION: I. g. e. cation or anion) by mixing with a suitable buffer and then stopping the flow immediately (this is known as the stopped-$ow technique). The rate of change of optical density is observed at a fixed and suitable wavelength. e. before and after mixing, are anhydrous, then, because protonation and deprotonation are practically instantaneous, no change in optical density should be observed after mixing. e. the ratio of the hydrated to anhydrous species is different before and after mixing), after mixing there should be a rate of change of optical density corresponding to an increase or decrease of the hydrated or anhydrous species, or vice versa.