. 2014 Jun 22;136(28):9925–9937. doi: 10.1021/ja503105b

Table 1. Phenol BDE’s, Redox Potentials (E_ox), Second-Order Rate Constants (183 K) for p-X-DTBP Phenol Oxidations by 2 and 4 and Reaction Yields (See Figure S10 for Kinetics Details).

substituent (X)		BDE^a (kcal mol^–1)	E_ox, V (vs Fc/Fc⁺)^c	k₂ of 2^d (M^–1 s^–1)	k₂^C of 4^d (M^–1 s^–1)	DTBQ yield (%)
OR	OCH₂CH₃		0.532	24	714
	OCH₃	79.6	0.526	23	520	49
	OCD₃		0.496	21	513
	OCH₃, −OD		0.585	2.1	58
	OMPP^b		0.614	0.84	350	44
	OCH₂CF₃		0.805	0.81	329
R	CH₃	80.1	0.81	0.042	185
	CH₂CH₃	80.0	0.875	0.027	160
	sec-butyl		0.884	0.023	152
	CH₃, −OD		0.896	0.010
	tert-butyl	82.3	0.927	0.008	106	38
	H	82.7	1.074	NR

Bond dissociation energy in DMSO.³¹

OMPP = 2-methyl-1-phenylpropan-2-yloxy.

These were determined from SHACV measurements; see Experimental Section. The experimental error is ±0.01 V.

The experimental error is ±5%.

Table 1. Phenol BDE’s, Redox Potentials (Eox), Second-Order Rate Constants (183 K) for p-X-DTBP Phenol Oxidations by 2 and 4 and Reaction Yields (See Figure S10 for Kinetics Details).