. Author manuscript; available in PMC: 2014 Nov 27.

Published in final edited form as: J Am Chem Soc. 2013 Nov 13;135(47):10.1021/ja407407h. doi: 10.1021/ja407407h

Table 2.

Rates of reaction of aldehydes and ketones with phenyllydrazine and other hydrazines in aqueous buffer at pH 7.4.^a

	k_(obs) (min⁻¹)	k_2(app) (M⁻¹sec⁻¹)	k_rel		k_(obs) (min⁻¹)	k_2(app) (M⁻¹sec⁻¹)	k_rel
Carbohydrates				Bulky hydrazine (ϕ₂NNK₂)
20	0.013 (0.003)	0.22 (0.02)	6.7	32	0.051 (0.024)	0.85 (0.13)	25
21	0.011 (0.001)	0.18 (0.02)	5.2	33	0.024 (0.012)	0.40 (0.27)	12
22	0.032 (0.002)	0.53 (0.03)	16	34	0.009 (0.003)	0.15 (0.05)	4.5
Acid/Base substituents				35	0.010 (0.005)	0.17 (0.08)	5.2
23	0.045 (0.025)	0.75 (0.42)	23	36	0.007 (0.001)	0.12 (0.01)	3.6
24	0.010 (0.002)	0.16 (0.02)	4.8	2-Carboxyphenylhydrazine
25	0.014 (0.001)	0.24 (0.02)	7.1	37	1.5 (0.2)	24 (3)	710
26	0.022 (0.006)	0.37 (0.10)	11	38	0.021 (0.004)	0.35 (0.07)	10
27	0.018 (0.006)	0.30 (0.10)	9.0	39	0.077 (0.006)	1.3 (0.1)	39
28	0.036 (0.012)	0.58 (0.25)	17	40	0.11 (0.02)	1.9 (0.4)	57
29	0.025 (0.001)	0.42 (0.02)	12	41	0.16 (0.03)	2.7 (0.5)	81
30	0.050 (0.004)	0.83 (0.07)	25	42	0.14 (0.03)	2.4 (0.4)	73
31	0.036 (0.010)	0.60 (0.17)	18	43	0.16 (0.02)	2.7 (0.4)	81

Conditions as in Table 1. Values measured 3–6 times and averaged (standard deviations in parentheses). Pseudo-first-ordcr k_(obs) normalized to the standard 1 mM aldehyde concentration.