Journal of the American Chemical Society p. 6970 - 6975 (1985)
Update date:2022-08-05
Topics:
Streitwieser, Andrew Jr.
Vorpagel, Erich R.
Chen, Chia-Chung
The pKCsCHA values are reported for a number of symmetrically meta- and para-substituted diphenylmethanes.The pKCsCHA values for the meta series (Me, 33.8; OMe, 32.7; F, 29.9; CF3, 28.9; Ph, 32.3; H, 33.4) give a normal Hammett plot with ρ = 9.69.The para series (Me, 35.1; OMe,37.6; Ph, 30.8; NMe2, 38.6; SPh, 28.8; CN, 23.0; SO2Me, 22.4) do not fit attempted correlations with ?, the Yukawa-Tsuno modifications, or dual substituent parameter approaches.Electron-donating groups are more anion destabilizing than in other reference systems. "Amphoteric" substituents, those that stabilize both anions and cations (phenyl, thio, etc.), cause special problems in generalized correlations.
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