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Summary of Second-order Rate Constants for Reactions o f 2,4-Dinitrophenyl X-Substituted Benzenesulfonates ( 3a-g ) and 4- Nitrophenyl X-Substituted Benzenesulfonates ( 4a-g ) with Piperidinein 80 mol % H 2 O/20 mol % DMSO at 25.0 ± 0.1 o C a Entry X10 3 k N / M -1 s -1 34a 4‐NO 2 49900 6.65 b 3‐NO 2 -4.50 c 4‐Cl 15100 1.54 d H 11100 1.30 e 4‐NHCOMe - 0.699 f 4‐Me 8200 0.675 g 4‐MeO 5300 0.428 a Data for the reactions of ( 3a-g ) were taken from ref. 10a. A 4f4eρ x = 1.04R 2 = 0.9804g4d4c4b4a -0.5 0.0 0.5 1.0 σ -1.5-2.0-2.5-3.0-3.5-4.0 log k N / M -1 s -1 (A) ρ X = 1.04R 2 = 0.980 B 4g4f4e4d4c4b4aρ x = 0.72R 2 = 0.982 -1.5 -1.0 -0.5 0.0 0.5 1.0 1.5 σ +-1.5-2.0-3.0-3.5-4.0 log k N / M s -1 (B) ρ X = 0.72R 2 = 0.982 Figure 1. Hammett (A) and Brown-Okamoto (B) plots for piper-idinolysis of 4-nitrophenyl X-substituted phenyl benzenesulfonates ( 4a-g ) in 80 mol % H 2 O/20 mol % DMSO at 25.0 ± 0.1 o C. The identityof points is given in Table 1.x

Piperidinolysis of 4-Nitrophenyl X-Substituted Benzenesulfonates and Related Compounds: Effect of Changing Leaving Group and Electrophilic Center