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By Ramsay W., Donnan F.G.

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The relevant data are listed in Table X V I I . The authors interpreted the correlation in terms of the electronattracting field effect of the aromatic π-carbons (inductive effect), which stabilizes the aryl anion. 4 χ 10~ liters/mole sec. 9°) than 30 30 5 D 2» (a) A. I. Shatenshtein and E . A. Izrailevich, Zh. Fiz. , 28, 3 ( 1 9 5 4 ) ; (b) Ε . N. Yurygina, P. P. Alikhanov, E . A. Izrailevich, P. N. Manochkina, and A. I.. Shatenshtein, Zh. Fiz. , 34, 587 ( 1 9 6 0 ) ; (c) A. I. Shatenshtein, Advan.

Bugg, R . Desiderato, and R . L . Sass, J. Am. Chem. Soc, 86, 3157 (1964). 1 2 C O N J U G A T I V E EFFECTS 53 tricyanomethide and pyridinium dicyanomethylide. The tricyanomethide anion was almost planar and trigonal. 13 A above the plane occupied by the three nitrogen atoms. Each G—G=N unit made an angle of 3° with respect to its projection in this plane. were coplanar, and the G—C—G bond angle of the side chain was 119°. 13 A above the plane of the ring. Ν Tricyanomethide ion Ν Pyridinium dicyanomethylide A good example of the loss of acidity of a carbon acid due to steric inhibition of resonance of its conjugate base is found in the work of Bartlett and Woods.

Am. Chem. Soc, 86, 2003 (1964). A. Streitwieser, J r . , R . A. Caldwell, and M. R . Granger, J. Am. Chem. Soc, 86, 3578 (1964). 5, triptycene of 38, and methane of 40. Because of the enforced orientation of the orbitals of the triptycyl anion, little charge derealiza­ tion can occur. Thus the three phenyl groups exert an inductive effect great enough in triptycene to account for about 2 pK units on the MS AD scale. The experiment further suggests that the inductive effects of the phenyl groups in triphenylmethane make a substantial contribution to the acidifying properties of these groups.

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A system of physical chemistry by Ramsay W., Donnan F.G.


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