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Oligooxa[3n.3]paracyclophane Quinhydrones — Cation-Induced Charge-Transfer Absorptions and Structures of the Metal Complexes

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Bauer,  Helmut
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Matz,  Volker
Max Planck Institute for Medical Research, Max Planck Society;

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Lang,  Martina
Department of Molecular Neurobiology, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Bauer, H., Matz, V., Lang, M., Krieger, C., & Staab, H. A. (1994). Oligooxa[3n.3]paracyclophane Quinhydrones — Cation-Induced Charge-Transfer Absorptions and Structures of the Metal Complexes. Chemische Berichte, 127(10), 1993-2008. doi:10.1002/cber.19941271024.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-A9A5-1
Abstract
The intramolecular oligooxa[3n.3]paracyclophane quinhy-drones 2–5 (with n = 3 to 6) were synthesized and their interactions with alkali and alkaline earth metal and mercury(II) ions were studied by electron absorption and NMR spectroscopy. Remarkable enhancements of the CT absorptions were observed by complexation with metal ions of the pentaoxa[15.3]paracyclophane quinhydrone 4 and the hexaoxa[18.3]paracyclophane quinhydrone 5 to the corresponding complexes 6a–e and 7, respectively. The various donor-acceptor orientations and the crown ether-like complexation in the calcium complex 6d, the mercury complex 6e and the barium complex 7 were determined by X-ray analysis. Moreover, the X-ray structures of the tetramethoxy-2,5,8-trioxa[9.3]paracyclophane 8a, a precursor of the quinhydrone 2, and of the pentaoxa[15.3](2,5)-p-benzoquinonophane 20, the product of oxidative demethylation of the quinhydrone 4, are given. For comparison with the cyclic quinhydrones acyclic analogs are also described.