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Rac-aqua(4-methyl-oxazolidine-4-carboxylato)(nitrato)(1,10-phenanthroline)copper(II), the aldol condensation product of formaldehyde with the d- and l-(alaninato)aqua(1,10-phenanthroline)copper(II) nitrate

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Abstract

The d- and l-enantiomers of the ternary complex [Cu(phen)(ala)(H2O)]NO3 [phen = 1,10-phenanthroline; ala = alanine; l-enantiomer (1a); d-enantiomer (1b)] both undergo an aldol-type condensation with formaldehyde under mild acidic conditions to yield racemic rac-[Cu(phen)(4MeOCA)(H2O)(NO3)] (2) (4MeOCA = 4-methyl-oxazolidine-4-carboxylate). The precursors and the products were characterized by circular dichroism, FTIR, UV–Vis, fluorescence spectroscopy, molar conductivity and electrospray ionization mass spectrometry. The racemic nature of the product was established by X-ray crystallography . In the crystal structure, the copper atom has a tetragonally elongated octahedral geometry in which the water and an oxygen atom of a nitrate group are mutually trans. A possible mechanism for the racemization of the ligand is proposed.

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Acknowledgments

This work is supported by Malaysian MOSTI eSc fund 02-02-09-SF0036 and the Malaysian Ministry of Higher Education grant FRGS/1/2012/SG01/UTAR/01/01.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, 57000, Bukit Jalil, Kuala Lumpur, Malaysia

    Chew Hee Ng, Hui Meng Er & Ing Hong Ooi

  2. Faculty of Science, Universiti Tunku Abdul Rahman, 31900, Kampar, Perak, Malaysia

    Wai San Wang, Yip Foo Win & Kian-Eang Neo

  3. Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore, 637371, Singapore

    Rakesh Ganguly

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  1. Chew Hee Ng
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  2. Wai San Wang
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  6. Hui Meng Er
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Correspondence to Chew Hee Ng.

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Ng, C.H., Wang, W.S., Win, Y.F. et al. Rac-aqua(4-methyl-oxazolidine-4-carboxylato)(nitrato)(1,10-phenanthroline)copper(II), the aldol condensation product of formaldehyde with the d- and l-(alaninato)aqua(1,10-phenanthroline)copper(II) nitrate. Transit Met Chem 41, 563–571 (2016). https://doi.org/10.1007/s11243-016-0053-4

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