Organic Solutes in Aqueous Solutions

B12

B12

Aniline

Venkateswaran, K., Stadlbauer, J.M., Wu, Z., Gillis, H.A. and Walker, D.C.
J. Phys. Chem., 1996, 100, 3569.

Reaction:          C6H5NH3+ + Mu ® MuC6H5NH3+                             pH = 1 - 2

                        C6H5NH2 + Mu ® MuC6H5NH2                            pH > 4

Type of reaction: addition into benzene ring with Mu located at ortho, meta and para to NH2 substituents

a)      kM = (1.54 ± 0.4) x 1010 dm3mol-1s-1                                  pH = 1 - 2

b)      kM = (9 ± 3)  x 109 dm3mol-1s-1                                          pH = 4

KIE = kM / kH = 1.54 x 1010 / 1.3 x 109 = 12                                pH = 1 - 3

KIE = kM / kH = 9 x 109 / 2.4 x 109 = 4                                        pH > 4

kH = 1.3 x 109 dm3mol-1s-1 at pH = 3; kH = 2.4 x 109 dm3mol-1s-1 at pH 7.8 – 8.4

from: http://www.rcdc.nd.edu/compilations/HAtom/H.htm

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