By Alan R. Katritzky
Confirmed 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 incorporates a cumulative topic index.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 4
The ratio of the extinction coefficients allowed calculation of the extent of water-addition, which decreased from 99% 28 ADRIEN ALBERT AND w. L. F. ARMAREGO [Sec. 111. l to 1% in the order: unsubstituted > 6-Me > N-Me w 7-Me > 6,7-Me, > 4-Me > 4,6-Me2> 4,7-Me,. These results agree well with the pK2q values. 21Fig. 5 shows how the presence of the methyl group in the 4-position can partially block hydration of the 2-aminopteridine cation. When this (‘blocking effect” is assisted by the + M effect of another methyl group in the 7-position, blocking of hydration becomes complete.
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. Section 11,C). e. in position 7) to the carbon atom C-4, the tendency to hydrate is strongly reduced.
Hydrated 2-hydroxypteridine) 27s is rapidly mixed with several alkaline buffers, and the rate of change of optical density (do)in the different buffers is extrapolated to zero time. The optical density (do) is a measure of the concentration of the hydrated anion at the moment, and pH, of mixing. A plot of do against pH therefore gives the value of pKaY. 25 In the same way, but starting with the anhydrous anion of 2-hydroxypteridine, reliable values of the acidic pKaxhave been determined. From a knowledge of pKax,pK,eq, and pKayfor the acidic function, the ratio of the hydrated to the anhydrous species in the anion and the neutral molecule have been calculated.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky