Final Thoughts on Chemistry for Isoquinoline-4-carbonitrile

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pKR+ values have been measured for cation-pseudobase equilibration by 4-X-2-methylisoquinolinium cations (1) (X=Br, CONH2, COC6H5, CN, NO2) at 25 deg C, ionic strength 0.1.These pKR+ values are well correlated by Hammett equations using either ? or ?- para substituent constants.The best correlation gives: pKR+=-8.8 (+/-0.3) ?p- +16.5 (+/-0.2) (r=0.998).The value pKR+=16.29 measured by Cook et al. (Tetrahedron, 32, 1773 (1976) for the 2-methylisoquinolinium cation in dimethyl sulfoxide-water solutions is in reasonable agreement with this correlation equation.For the 2-methyl-5-nitrophthalazinium cation, pKR+=7.87, and pKRO-=12.10 for alkoxide ion formation by the pseudobase of this cation.The pH dependence of the pseudo first-order rate constants (kobs) for cation-pseudobase equilibration has been measured for 1_X=CONH2, COC6H5, CN and for the 2-methylphthalazinium cation (3) ans its 5-NO2 derivative (4).For each of these cations, kf=kOH<-OH>+kH2O and kd=k1+k2 and the parameters kOH kH2O, k1, and k2 have been evaluated.For 1_X=CONH2 and CN and 3, kOH is consistent with a correlation line between log KOH and pKR+ established for other isoquinolinium cations (J.Am.Chem.Soc. 99, 1189 (1977)).For 1_X=COC6H5, kOH is seven-fold smaller, and for 4, kOH is five-fold greater than prdicted by this correlation line.

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Reference：
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem