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. 2023 Jun 9;59(52):8091–8094. doi: 10.1039/d3cc01912h

Second-order rate constants k2 for the reactions of the enamines 4 or 5 with the benzhydrylium tetrafluoroborates 7 and Mayr nucleophilicity parameters for 4 and 5 (acetonitrile, 20 °C).

Enamine Electrophile Mayr Ea k 2 (M−1 s−1) N, sN
4 7d –7.02 7.06 × 101 9.25, 0.84
7e –7.69 2.14 × 101
7f –8.22 7.74
7g –8.76 2.42
5 7a –2.19 6.92 × 104 7.74, 0.87
7b –3.85 1.96 × 103
(1.75 × 103)b
7c –5.53 8.84 × 101
(5.49 × 101)b
a

Electrophilicity parameters E (as defined in eqn (1) and reported in ref. 13).

b

In dichloromethane. With further data in ESI, N(sN) = 7.06 (1.11) was calculated for 5 in CH2Cl2.