Table 6.

Electrochemical Properties of Modified 5-NIs

				mean ± SE
groupa	name	structure	R	E1/2 in DMSO (V vs Fc)b	Ep in water (V vs SCE)b,c
	40	I	phenyl	−1.593 ± 0.002	ND
	41	I	4-methylphenyl	−1.592 ± 0.003	ND
	42	I	4-bromophenyl	−1.592 ± 0.003	ND
	22	IV	2,3,4-trimethoxyphenyl	−1.584 ± 0.005	−0.757 ± 0.003
	27	IV	1,3-benzodioxolyl	−1.584 ± 0.001	−0.778 ± 0.002
	20	IV	3-methoxyphenyl	−1.580 ± 0.007	−0.763 ± 0.001
	Mz			−1.561 ± 0.001	−0.751 ± 0.017
	1-methyl-5-NI			−1.557 ± 0.001	ND
	34	II	4-methylphenyl	−1.557 ± 0.001	ND
	35	II	4-bromophenyl	−1.544 ± 0.001	ND
A	9	IV	2,4,6-trimethylphenyl	−1.529 ± 0.001	ND
	30	IV	2-thiopheneyl	−1.528 ± 0.003	−0.658 ± 0.001
	8	IV	4-methylphenyl	−1.522 ± 0.003	ND
C	23	IV	4-diethoxymethylphenyl	−1.518 ± 0.003	ND
	5	IV	phenyl	−1.517 ± 0.001	−0.634 ± 0.004
	7	IV	3-methylphenyl	−1.516 ± 0.001	−0.635 ± 0.003
	6	IV	2-methylphenyl	−1.512 ± 0.001	−0.621 ± 0.001
C	24	IV	2-biphenyl	−1.512 ± 0.001	ND
	26	IV	2-napthyl	−1.509 ± 0.001	ND
	31	IV	3-thiopheneyl	−1.508 ± 0.002	−0.595 ± 0.001
C	12	IV	4-bromophenyl	−1.506 ± 0.002	−0.605 ± 0.007
	29	IV	2-furanyl	−1.504 ± 0.003	ND
A	15	IV	4-chlorophenyl	−1.503 ± 0.001	−0.584 ± 0.001
	25	IV	1-napthyl	−1.502 ± 0.004	ND
A	19	IV	3-fluorophenyl	−1.502 ± 0.001	−0.613 ± 0.008
C	28	IV	1-methylimidazolyl	−1.497 ± 0.001	−0.594 ± 0.014
A	11	IV	3-bromophenyl	−1.497 ± 0.005	ND
	18	IV	3-iodophenyl	−1.494 ± 0.004	ND
B	33	III	4-bromophenyl	−1.493d ± 0.004	ND
	14	IV	3-chlorophenyl	−1.492 ± 0.002	ND
	3	III	4-methylphenyl	−1.489d ± 0.001	ND
	21	IV	4-trifluoromethoxyphenyl	−1.487 ± 0.001	ND
	13	IV	2-chlorophenyl	−1.486 ± 0.004	ND
B	10	IV	2-bromophenyl	−1.481 ± 0.001	ND
	16	IV	2,4-dichlorophenyl	−1.469 ± 0.002	ND

^aGroup refers to the Mz resistance groups in Figure 3A and Table 5.

^bRedox activation potential was determined by cyclic voltammetry in DMSO or water (pH 7.0). Half-wave potential (E_1/2) of the one-electron transfer reaction (0/−1 reduction) was determined in DMSO, with ferrocene (Fc) as the internal reference. Peak potential, E_p, for the irreversible first electron reduction step was determined in water, using a saturated calomel electrode (SCE) as standard. Data are mean ± SE of three to four separate experiments.

^cND, not determined.

^dThe E_1/2 values for these compounds are for the reversible wave, but given the different electrochemical response, these values can not be directly compared to the other E_1/2 values.