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. 2007 Jan 22;46(2):351-3.
doi: 10.1021/ic0614869.

1,2-HOIQO--a highly versatile 1,2-HOPO analogue

Michael Seitz  1 , Michael D Pluth, Kenneth N Raymond
Affiliations

1,2-HOIQO--a highly versatile 1,2-HOPO analogue

Michael Seitz et al. Inorg Chem. .

Abstract

A cyclic, bidentate hydroxamic acid binding unit based on an isoquinoline scaffold has been utilized for the synthesis of a hexadentate tripodal ligand based on the TREN backbone. This prototype for a new class of multidentate chelators forms mononuclear iron(III) complexes and one-dimensional coordination polymers with lanthanide(III) cations. The latter has been determined by single-crystal X-ray analysis of the cerium species. The solid-state structure in the monoclinic space group P2(1)/c (C(36)H(34)CeN(7)O(11), a = 12.341(2) A, b = 26.649(4) A, c = 10.621(2) A, alpha = gamma = 90 degrees, beta = 96.753(3) degrees, V = 3468.6(9) A3, Z = 4) exhibits a trigonal-dodecahedral environment around the cerium cation. The proof of concept for the versatility of the new scaffold has been shown by the modification of the crucial precursor 3-carboxyisocoumarin through electrophilic aromatic substitutions to yield the corresponding chlorosulfonated and nitrated analogues.

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Figures

Figure 1
Figure 1
1,2-HOPO (left) and 1,2-HOIQO (right).
Figure 2
Figure 2
Asymmetric unit of [Ce(7)(H2O)]·H2O (9·H2O). Thermal ellipsoid plot (Ortep 3 for Windows, 50% probability level) with atom numbering scheme. Hydrogens and the isolated water molecule are omitted for clarity.
Figure 3
Figure 3
Part of the extended one-dimensional chain for the complex [Ce(7)(H2O)]·H2O (9·H2O). Hydrogens and the isolated molecule of water in the crystal omitted for clarity (Mercury 1.4).
Figure 4
Figure 4
π- π-Stacking of the 1,2-HOIQO rings in [Ce(TREN-1,2-HOIQO)(H2O)]*H2O(9*H2O). Hydrogens and the isolated molecule of water in the crystal omitted for clarity (Mercury 1.4).
Scheme 1
Scheme 1
Synthesis of TREN-1,2-HOIQO (7).
Scheme 2
Scheme 2
Synthesis of metal complexes with TREN-1,2-HOIQO.
Scheme 3
Scheme 3
Electrophilic aromatic substitution of isocoumarin 3.
See this image and copyright information in PMC

References

    1. Gorden AEV, Xu J, Raymond KN, Durbin PW. Chem Rev. 2003;103:4207. and refs cited therein. - PubMed
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    1. Raymond KN, Scarrow RC, White DL. 796815. patent US. 1987
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    1. Moore EG, Xu J, Jocher CJ, Werner EJ, Raymond KN. J Am Chem Soc. 2006;128:10648–10649. - PubMed
    1. Johnston HW, Kaslow CE, Langsjoen A, Shriner RL. J Org Chem. 1948;13:477–483. - PubMed

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