Kinetics of the nucleophilic aromatic substitution reactions of 7-L-4nitrobenzofurazans 1 (1a: L = Cl and 1b: L = OCH 3 ) and secondary cyclic amines (morpholine, piperidine, and pyrolidine) 2a-c have been measured in acetonitrile solution at 20°C. The derived values of second-order rate constants (k 1 ) have been employed to determine the electrophilicity parameters E for both benzofurazans 1a and 1b according to the linear free enthalpy relationship: log k (20°C) = s N (E + N) (Eq. (1)). The second-order rate constants for reactions of benzofurazans 1 with a series of 4-X-substituted anilines 3a-d (X = OH, OCH 3 , CH 3 , and H) have also been measured in MeCN and found to agree within a factor of 0.14-50 with those calculated by Eq. (1) from the electrophilicity parameters E measured in this work and the known nucleophile-specific parameters N and s N of anilines 3. On the other hand, the reactions of these benzofurazans 1 with anilines 3 exhibit linear Brønsted-type plots with β nuc = 1.27 for 1a and 1.01 for 1b, which are considerably greater than those (0.57 for 1a and 0.62 for 1b) obtained with the secondary cyclic amines 2. These high values of β nuc have been interpreted