Chemistry Reference
In-Depth Information
6.3.1.2  Iron(IV)-  and  Iron(V)-Oxo  Complexes.  The redox properties of
nonheme Fe IV =O complexes have been examined [279, 328-332]. The Fe IV =O
species generally undergoes a H-atom abstracting ability in the order
Fe IV =O >> Fe IV -O-Fe > Fe IV -OH [328]. Among the studied Fe IV =O complexes,
[Fe IV (O)(N4Py)] 2+ (N4Oy = N , N -bis(2-pyridylmethyl)-bis(2-pyridyl)methyl-
amine) had the ability to oxidize C-H bonds, even in cyclohexane (D C-H =
99.3 kcal/mol) [333]. The [Fe IV (O)(N4Py)] 2+ has been synthesized using chemi-
cal, electrochemical, and photocatalytical methods [334-336]. The theoretical
study supports the involvement of proton-coupled electron transfer in the
O-O cleavage to result in oxoiron(IV) from the reaction of nonheme iron(II)
complex with H 2 O 2 [337].
Recently, the rate constants for the oxidation of dihydroanthracene (DHA)
by [Fe IV (O)(N4Py)] 2+ ( k 2 , M/s) as a function of D O-H were compared with
other oxo complexes of Fe(IV), Ru(IV), and Mn to understand the transfer
of a proton associated with the one-electron transfer process, responsible for
the conversion of the Fe IV =O unit to the Fe III -OH species (Fig. 6.28) [329,
338-342]. The straight line in the plot of Figure 6.28 was constructed using
appropriate values for t BuO and t BuOO . This approach was used previously
8
t BuO
4
Ru IV
1 (25°C)
t BuOO
1 (-15°C)
MnO 4 -
0
Fe IV O(TMP) (-15°C)
Mn(O)(OH)
-4
Mn(OH) 2
Mn 2 O 2
Mn 2 (O)(OH)
-8
65
75
85
95
105
D O-H (kcal/mol)
Figure 6.28. Plot of log k 2 of DHA oxidation and the strength of the O - H bond formed
by the oxidants in CH 3 CN at 25°C unless labeled otherwise. Data points shown in black
filled squares were taken from References 32-37 and the blue filled circle was obtained
in the present work of complex 1 . The red straight line was drawn through the points
belonging to the two oxygen radicals following Mayer's precedent. Mn(O)(OH),
[Mn IV (Me2EBC)(O)(OH)] + ; Mn(OH) 2 , [Mn IV (Me 2 EBC)(OH) 2 ] 2+ ; Mn 2 O 2 , [(phen) 2 Mn IV
(O) 2 Mn III -(phen) 2 ] 3+ ; Mn 2 (O)(OH), [(phen) 2 Mn III (O)(OH)Mn III (phen) 2 ] 3+ ; Ru IV O,
[Ru IV (O)(bpy) 2 (py)] 2+ (adapted from Wang et al. [329] with the permission of the
American Chemical Society). See color insert.
 
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