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New copper(II) 2-(alkylamino)troponates

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Abstract

The copper aminotropones Cu[ON(R′)C7H4R-4]2 [R = H, R′ = Me (13), Et (14), n-Pr (15), n-Bu (16), Bz (17), MenOCH2CH2 (20); R = i-Pr, R′ = Me (18), n-Pr (19), MenOCH2CH2 (21)] have been prepared from the corresponding aminotropones HN(R′)OC7H4R-4 (1–7) by reacting with copper(II) acetate in aqueous ethanol. 20, 21 contain the flavourant, menthol, as part of the ligand. The structures of 5 (R = H, R′ = Bz), a hydrogen-bonded dimer, 14 and 20, both incorporating square-planar, four-coordinate copper centres, have been determined by X-ray crystallography. The antibacterial activities of complexes 13, 17, 20 and 21 have been assayed against Staphylococcus waneri, an in vitro model of plaque inhibition effects, and found to be more active than a commercial toothpaste formulation, but less active than the O,O-chelated copper(II) complex of ethylmaltol.

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Authors and Affiliations

  1. Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK

    Marie C. Barret, Purvi H. Bhatia, Gabriele Kociok-Köhn & Kieran C. Molloy

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  1. Marie C. Barret
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  2. Purvi H. Bhatia
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  3. Gabriele Kociok-Köhn
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  4. Kieran C. Molloy
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Correspondence to Kieran C. Molloy.

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Barret, M.C., Bhatia, P.H., Kociok-Köhn, G. et al. New copper(II) 2-(alkylamino)troponates. Transition Met Chem 39, 543–551 (2014). https://doi.org/10.1007/s11243-014-9830-0

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