Abstract
The rate constants for basic deuterium exchange of the methyl group (kD) in 2-phenyl-5-methyl-tetrazole (I) and 1-aryl-5-methyltetrazole (II) and its derivatives with a polar substituent (R) in the phenyl ring were measured. The increased CH acidity of II as compared with I [kD(II)/kD(I)∼20] is in agreement with the calculated and experimental values regarding the character of the electron-density distribution in the molecules. The effect of R on the rate of deuterium exchange of the methyl group correlates with the σ° constants (ρ=3.0, r = 0.997). The results of measurement of the kinetic isotope effect during deuterium (tritium) exchange in II (kD/kT∼1.8) are discussed in connection with the peculiarities of the stepwise reaction mechanism.
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