COPPER(II) CATALYZED OXIDATION OF 2-AMINOMETHYL- PYRIDINE: SYNTHESIS AND STRUCTURE OF [(N,N-BIS(2-PYRIDINECARBONYL)IMIDATO-kN)(PYRIDINE-2-CARBONYLAMIDE-kO)COPPER(II)] NITRATE DIHYDRATE

Mark M. Turnbull, Sandra Bruda, Jan L. Wikaira

Abstract


The title compound is formed by the air oxidation of 2-aminomethylpyridine in 95% ethanol in the presence of copper(II) nitrate with condensation of the resulting picolinamide molecules in situ to form the imide moiety. The compound crystallizes as a dihydrate (one water position is only 75% occupied) and the Cu(II) ion is 5-coordinate square-pyramidal, the basal plane being occupied by four nitrogen atoms (three from pyridine rings and the fourth being the imide N-atom) in a nearly planar array [mean deviation = 0.28(3) Å) with the Cu(II) ion slightly above the plane [0.128(9) Å]. The axial position is occupied by the carbonyl oxygen atom of a coordinated picolinamide [Cu-O = 2.273(10) Å]. The crystal is stabilized by multiple hydrogen bonding interactions with both water molecules and the amide NH2 serving as donors and the nitrate ion, imide oxygen atoms and water molecules serving as acceptors.

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DOI: http://dx.doi.org/10.17628/ecb.2013.2.1038-1040

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