. Author manuscript; available in PMC: 2018 Mar 1.

Published in final edited form as: J Am Chem Soc. 2017 Feb 14;139(8):3186–3195. doi: 10.1021/jacs.6b12990

Table 2.

Kinetic Parameters of O–H Oxidation Reactions by O^MeAN-LA

substrate	BDE (H^•) (kcal/mol)	E⁰ (V vs Fc^+/0)	k^OMeAN32H+ (M⁻¹ s⁻¹)	k^OMeAN3Sc3+ (M⁻¹ s⁻¹)	k^OMeAN32BR3 (M⁻¹ s⁻¹)	notes
4-MeO-PhOH	80.9	1.01	64 ± 1	53 ± 1	2.9 ± 0.2	^a
4-MeO-PhOD		1.01	52 ± 1 (KIE: 1.25)	42 ± 1 (KIE: 1.19)	2.4 ± 0.1 (KIE: 1.17)	^a
2,4-^tBu₂-PhOH	81.9	1.04	1.8 ± 0.2	1.1 ± 0.1	0.12 ± 0.01	yield: 60–70%
4-PhO-PhOH		1.07	0.51 ± 0.02	0.44 ± 0.02	0.046 ± 0.001	^a
4-^tBu-PhOH		1.10	0.025 ± 0.001	0.023 ± 0.001	0.0027 ± 0.0003	^a
4-Me-PhOH	84.6	1.12	0.035 ± 0.002	0.027 ± 0.001	0.0024 ± 0.0002	^a
4-Cl-PhOH	85.7	1.21	no reaction	no reaction	no reaction	no decay (t = 1 h)

Product not quantified (see text and Supporting Information).