. Author manuscript; available in PMC: 2013 Mar 7.

Published in final edited form as: Chem Res Toxicol. 2010 May 17;23(5):880–887. doi: 10.1021/tx900432d

Table 1.

EC₂ values for aniline-induced MPO free radical formation and physicochemical parameters for anilines.

	EC₂	log EC₂	σ ¹	log P²	EA-R³	IP-R³	IP-P³	EA-P³
aniline	20.5	1.31	0	0.9	4.96	9.97	8.53	−0.64
p-toluidine	3.1	0.49	−0.14	1.39	4.92	9.95	8.35	−0.61
m-toluidine	8.9	0.95	−0.06	1.4	4.90	9.89	8.48	−0.59
o-toluidine	3.6	0.56	0.1	1.32	4.91	9.93	8.44	−0.60
p-anisidine	--*	--	−0.28	0.95
m-anisidine	6.8	0.83	0.11	0.93	5.03	10.01	8.50	−0.62
o-anisidine	3.6	0.56	0	1.18	5.04	10.06	8.26	−0.57
3,4-dimethylaniline	2.7	0.43	−0.2	1.84	4.88	9.88	8.32	−0.61
2,4-dimethylaniline	2.4	0.38	−0.04	1.68	4.89	9.92	8.28	−0.61
2,6-dimethylaniline	7.3	0.86	0.2	1.84	4.89	9.92	8.35	−0.60
3,4-dimethoxyaniline	--	--	−0.17
2,4-dimethoxyaniline	--	--	−0.28
4-chloroaniline	19.3	1.29	0.24	1.83	5.24	10.26	8.60	−0.28
3-chloroaniline	248	2.39	0.37	1.88	5.26	10.22	8.73	−0.26
2-chloroaniline	61.2	1.79	0.67	1.9	5.32	10.31	8.62	−0.29
4-fluoroaniline	16.3	1.21	0.06	1.15	5.27	10.34	8.55	−0.29
2,4-dichloroaniline	67.6	1.83	0.91	2.78	5.58	10.58	8.68	−0.01
3,4-dichloroaniline	455	2.66	0.61	2.69	5.49	10.46	8.74	−0.00
2,6-dichloroaniline	733	2.87	1.34	2.76	5.67	10.64	8.73	0.01
4-nitroaniline	345	2.54	0.78	1.39	5.89	10.93	9.27	0.78
3-nitroaniline	--	--	0.74	1.37
2-nitroaniline	--	--	1.72	1.85
4-ethylaniline	2.4	0.38	−0.15	1.96	4.92	9.94	8.33	−0.65
4-aminosalicylate	29.8	1.47	0.57	0.89	6.00	11.1	9.47	0.52
4-chloro-2-methylaniline	3.64	0.56	0.34	2.1	5.20	10.23	8.51	−0.29
4-aminobenzonitrile	279	2.45	0.7	0.9	5.49	10.53	8.87	0.19

aminoglutethimide	1.5	0.176	−0.15⁴	1.1			8.30
procainamide	3.2	0.505	0.36⁵	0.88			8.43

From Perrin et al., 1981.

From Tetko, I. V.; Gasteiger, J.; Todeschini, R.; Mauri, A.; Livingstone, D.; Ertl, P.; Palyulin, V. A.; Radchenko, E. V.; Zefirov, N. S.; Makarenko, A. S.; Tanchuk, V. Y.; Prokopenko, V. V. Virtual computational chemistry laboratory - design and description, J. Comput. Aid. Mol. Des., 2005, 19, 453–63 (http://www.vcclab.org).

Values were determined by MOPAC calculations as described in Materials & Methods. EA-R, electron affinity of the radical metabolite; IP-R, ionization potential of the radical metabolite; IP-P, ionization potential of the parent aniline; EA-P, electron affinity of the parent aniline.

⁴

Value for –C(CH₃)₃.

⁵

Value for –CONHCH₃.