Abstract
The synthesis and X-ray structure of a new pendant-arm derivative of a parent 14-membered N2O2-donor macrocycle bearing an N-substituted 6-methylene-2,4-dimethylphenol group is presented. A single crystal X-ray study shows a strong intramolecular hydrogen-bond between the pendant phenol proton and the tertiary nitrogen of the macrocyclic ring, which may inhibit its ability to bind with selected transition and post-transition metal ions.
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Bernhardt, P.V., Lawrance, G.A.: Complexes of polyaza macrocycles bearing pendant coordinating groups. Coord. Chem. Rev. 104, 297–343 (1990)
Wainwright, K.P.: Applications for polyaza macrocycles with nitrogen-attached pendant arms. Adv. Inorg. Chem. 52, 293–334 (2001)
Ferraudi, G., Canales, J.C., Kharisov, B., Costamagna, J., Zagal, J.G., Cardenas-Jiron, G., Paez, M.: Synthetic N-substituted metal aza-macrocyclic complexes: properties and applications. J. Coord. Chem. 58, 89–109 (2005)
Lindoy, L.F., Skelton, B.W., Smith, S.V., White, A.H.: New macrocyclic ligands. III Pendant 2-pyridylmethyl and diethylaminoethyl arm derivatives of dibenzo-substituted O2N2-donor rings. The X-ray structure of a pendant 2-pyridylmethyl derivative. Aust. J. Chem. 46, 363–375 (1993)
Adam, K.R., Lindoy, L.F., Skelton, B.W., Smith, S.V., White, A.H.: The interaction of transition-and post-transition-metal ions with O2N2-donor macrocycles incorporating pendant pyridyl methyl groups. J. Chem. Soc. Dalton Trans. 3361–3367 (1994)
Fenton, R.R., Lindoy, L.F., Luckay, R.C., Turville, F.R., Wei, G.: New macrocyclic ligands. XII Phosphonic and phosphinic acid pendant arm derivatives of mixed donor macrocycles: towards new selective reagents for lead(II). Aust. J. Chem. 54, 59–62 (2001)
Atkinson, I.M., Chartres, J.D., Everett, G.W., Ji, X.-K., Lindoy, L.F., Matthews, O.A., Meehan, G.V., Skelton, B.W., Wei, G., White, A.H.: Macrocyclic ligand design. Interaction of selected transition and post-transition metal ions with a new O2N2-donor macrocycle incorporating a methylpyridyl pendant arm. J. Chem. Soc. Dalton Trans. 1191–1198 (2000)
Clegg, J.K., Lindoy, L.F., Thuéry, P., Lee, Y.H., Kusumohastuti, D.K.A., Mora, C., Kim, H.H., Cho, J.H., Kim, Y.: Copper(II), iron(III) and cobalt(III) complexes of the pendant-arm cyclam derivative 6,6,13-trimethyl-13-amino-1,4,8,11-tetraazacyclotetradecane. J. Incl. Phen. Mac. Chem. 65, 49–57 (2009)
Lindoy, L.F.: The Chemistry of Macrocyclic Ligand Complexes. Cambridge University Press, Cambridge (1989)
Sheldrick, G.M.: A short history of SHELX. Acta Crystallogr. A 64, 112–122 (2008)
Kimura, E., Koike, T., Takahashi, M.: Novel synthesis and complex properties of macrocyclic tetra-amines appended with phenol as an axial donor. J. Chem. Soc. Chem. Commun. 385–386 (1985)
Iitaka, Y., Koike, T., Kimura, E.: Molecular structure of a nickel(II) complex with phenolate-appended cyclam. Inorg. Chem. 25, 402–404 (1986)
Kimura, E., Koike, T., Uenishi, K., Hediger, M., Kuramoto, M., Joko, S., Arai, Y., Kodama, M., Iitaka, Y.: New-dimensional cyclam. Synthesis, crystal structure, and chemical properties of macrocyclic tetraamines bearing a phenol pendant. Inorg. Chem. 26, 2975–2983 (1987)
Kimura, E., Koike, T., Toriumi, K.: A trigonal bipyramidal zinc(II) complex of a phenol-pendant macrocyclic triamine. Inorg. Chem. 27, 3687–3688 (1988)
Zhu, S., Kou, F., Lin, H., Lin, C., Lin, M., Chen, Y.: Synthesis of novel macrocyclic polyamines with a pendant phenol group and properties and structures of their copper(II) complexes. Inorg. Chem. 35, 5851–5859 (1996)
Stockheim, C., Hoster, L., Weyhermüller, T., Wieghardt, K., Nuber, B.: First-row transition-metal complexes of mixed ‘pendant-arm’ derivatives of 1,4,7-triazacyclononane containing phenolate and carboxylate functional groups. J. Chem. Soc. Dalton Trans. 4409–4416 (1996)
Zhang, X.X., Bordunov, A.V., Kou, X., Dalley, N.K., Izatt, R.M., Mangum, J.H., Li, D., Bradshaw, J.S., Hellier, P.C.: Thermodynamic, spectroscopic, and structural studies of complexation of phenol- and pyridine-armed macrocyclic ligands with univalent metal ions. Inorg. Chem. 36, 2586–2593 (1997)
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We thank the Australian Research Council for support.
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A tribute to the outstanding contribution of Len Lindoy to Inorganic, Macrocyclic and Supramolecular Chemistry.
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Ji, XK., Lindoy, L.F., Skelton, B.W. et al. Inhibition of metal ion complexation by an N2O2-donor macrocycle by incorporation of an intramolecularly hydrogen-bonding pendant phenolic group. J Incl Phenom Macrocycl Chem 71, 589–592 (2011). https://doi.org/10.1007/s10847-011-9988-4
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DOI: https://doi.org/10.1007/s10847-011-9988-4