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. Author manuscript; available in PMC: 2012 Mar 9.
Published in final edited form as: J Am Chem Soc. 2011 Feb 16;133(9):3173–3183. doi: 10.1021/ja110795m

Table 5.

Rate and Equilibrium Constants for Carbon Deprotonation of Glycine and Glycine Derivatives in Water at 25 °C and I = 1.0 (KCl)

Carbon Acid kHOa (M−1s−1) pKab Carbon Acid kHOa (M−1s−1) pKab
graphic file with name nihms273962t7.jpg 4.5 × 10−5 c 28.9c graphic file with name nihms273962t8.jpg 4.1c 21.0c
graphic file with name nihms273962t9.jpg 3.3 × 10−4 c 27.3c graphic file with name nihms273962t10.jpg 390c 18.0c
graphic file with name nihms273962t11.jpg 2.9 21.9 graphic file with name nihms273962t12.jpg 9.0 × 103 d 14d
graphic file with name nihms273962t13.jpg 2.0 × 10−4 27 graphic file with name nihms273962t14.jpg ca. 1 ca. 23
graphic file with name nihms273962t15.jpg 0.13 25 graphic file with name nihms273962t16.jpg 1.1 × 104 d 14d
graphic file with name nihms273962t17.jpg not determined ca. 23 e graphic file with name nihms273962t18.jpg 7.5 × 102 f 17f
a

Second-order rate constant for deprotonation of the carbon acid by hydroxide ion calculated from data reported in this work, unless noted otherwise.

b

pKa for ionization of the carbon acid in water calculated from data reported in this work, unless noted otherwise.

c

Data from ref 2.

d

Data from ref 28.

e

Estimated as described in the text.

f

Data from ref 29.