By O. A. Reutov

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Extra info for CH–Acids. A Guide to All Existing Problems of CH-Acidity with New Experimental Methods and Data, Including Indirect Electrochemical, Kinetic and Thermodynamic Studies

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36. 37. 38. 5<* Reference 146,148,149 150 146,148,149 146,148,149 150 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 151 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 152 a Notation: Biph, o,oT-biphenylene; Phen, 4,5-phenanthrylene. b The standard acid for Compounds 3-7. c The standard acid for Compounds 9-13, 15, 16, 18-29 and 32. d The standard acid for Compounds 31, 33-38. DBBiph, 3,4,5,6-dibenzobiphenylene; Polycyano CH-acids were studied in H 2 S04/H 2 0 (1 to 70%) and HC104/H20 (1 to 70%) mixtures 25 , or in DMS0/Pr3N (1 x 10"3M), DMS0/Et0H/Et0Na, DMS0/CH3C00H/CH3C00Na (1 x 10-2M) llt8 1I+9, The acidic hydrocarbons in Table 21 have extensive π -electron systems, so that the formation of carbanions should, first of all, affect the π electron energy.

The first half-wave potentials correlate fairly well with the pKa of the respective carbanions 13 *. The same was found for pKa(RCOOH) and Ej ((RCOO)2Hg)) in methanol, DMF, and DMSO 1 3 9 . Table 18 compares the polarographic data with acidities found by other investigators. The data in the last column were obtained by various techniques, (trans-metalation equilibria, kinetic acidity, HMO calculations, indirect methods) in various solvents such as DMSO, dimethoxyethane, methanol, etc. Nevertheless, there is a good agreement between the pKa values.

19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 5<* Reference 146,148,149 150 146,148,149 146,148,149 150 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 151 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 146,148,149 152 a Notation: Biph, o,oT-biphenylene; Phen, 4,5-phenanthrylene. b The standard acid for Compounds 3-7. c The standard acid for Compounds 9-13, 15, 16, 18-29 and 32.

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