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Carbon acidity. 60. Effect of temperature on ion pair acidities of pentafluorobenzene. Nature of pentafluorophenylcesium and -lithium ion pairs in cyclohexylamine.

✍ Scribed by Andrew Streitwieser Jr.; Chien C.C. Shen


Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
189 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis


The ion pair equilibrium between 9-t-butylfluorene and pentafluorobenzene in cyclohexylamine has almost zero entropy for their cesium salts but a relatively high entropy change, 21.5 e.u., for their lithium salts. Both pentafluorophenylcesium and -lithium exist primarily as contact ion pairs in cyclohexylamine. The brilliant pioneering studies of Hogen-Esch and Smid (2) have established that carbanion alkali metal pairs in solution may range from tight or contact ion pairs to loose or solventseparated pairs.


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The ion pair acidities of several sulfones were measured on the cesium-cyclohexylamine scale. Cyclopropyl phenyl sulfone is less acidic than isopropyl phenyl sulfone in agreement with earlier results in dimethyl sulfoxide. The acidities of a series of substituted phenyl methyl sulfones show that the