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that it will not be able to participate in aqueous Fenton reactions.
Table 1 shows that in all cases the formal potential ranged between
20.78 and 20.97 V vs. Ag/AgCl, much lower than the DFO
complex (20.67 V).2 Indeed, immediately upon addition of
iron(II)–BHT complexes to aqueous solutions the solutions turned
purple indicating the oxidation of the complex.
In summary, BHTs provide a new general group of side-
rophores. Their high iron(III) affinity, low redox potential,
tridentate character, small size and above all the versatility of
their synthesis which allows tuning of their physico-chemical
properties open the door for widely different potential applications
in medicine, plant nutrition, analysis and bioanalysis.
14 M. A. Smith, P. L. R. Harris, L. M. Sayre and G. Perry, Proc. Natl.
Acad. Sci. USA, 1997, 94, 9866–9868.
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Klinke, M. Zabel and B. Koenig, Dalton Trans., 2003, 141–145.
16 Experimental procedures and full characterization are contained in the
ESI{.
17 Several hydroxyamino 1,3,5-triazines synthesized previously: J. T. Shaw,
E. R. Nicottra and R. K. Madison, J. Org. Chem., 1962, 27,
4054–4056.
We are grateful to the European Union for partial funding
under the Aquachem network (contract MRTN-CT-2003-503864)
and the financial support of the ISF—Israel Science Foundation
(Grant No. 176/02-1).
Notes and references
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19 Crystal data for the complex: C19H33FeN12O7 Mr 5 597.42, black–
violet blocks, 0.23 6 0.20 6 0.16, triclinic, space group P-1,
a 5 11.4324(9), b 5 13.9381(11), c 5 17.3580(14), a 5 92.2360(10)u,
3
˚
b 5 101.4470(10)u, c 5 92.2080(10)u, V 5 2705.8(4) A , Z 5 4,
rcalcd 5 1.467 g cm23, m 5 0.620 mm21, F(000) 1252, T 5 295(1) K;
Bruker SMART diffractometer using graphite-monochromated MoKa
radiation. The structure was solved and refined by automatic direct
methods SHELXL-97. All non-hydrogen atoms were refined aniso-
tropically. Hydrogen atoms were assigned idealized positions and were
included in structure-factor calculations. R1 5 0.0846, wR2 5 0.1175,
11703 independent reflections [2H 5 54u] and 729 parameters. CCDC
in CIF or other electronic format.
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J. Wiley and Sons, NY 2001.
This journal is ß The Royal Society of Chemistry 2005
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