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DOI: 10.1039/A706676G (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1998, 345-352

Stereochemistry of nickel(II) complexes with N-glycosylamine ligands from 1,3-diaminopropane and aldopentoses. Correlation between configurational structures and circular dichroism spectra†

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Tomoaki Tanase, Yukiko Yasuda, Tomoko Onaka and Shigenobu Yano

Abstract

Reactions of [Ni(tn)3]X2·2H2O (tn = 1,3-diaminopropane, X = Cl or Br) with aldopentoses afforded a series of mononuclear nickel(II) complexes with N-glycosylamine ligands, [Ni(aldose-tn)2]X2 [aldose-tn = 1-(N-aldosyl)amino-3-aminopropane, aldose = D-xylose (D-Xyl) 1, D-lyxose (D-Lyx) 2, D-ribose (D-Rib) 3, or D-arabinose (D-Ara) 4], which were characterized by elemental analysis, electronic absorption and circular dichroism (CD) spectroscopy, and X-ray crystallography. Compound 4b, [Ni(D-Ara-tn)2]Br2·2H2O, was shown by an X-ray analysis to have a C2 symmetrical mononuclear nickel(II) structure ligated by two tridentate N-glycosylamine ligands, 1-amino-3-(N-D-arabinosyl)propane. The two N-glycosylamines are co-ordinated to the metal through the primary amino and N-glycosidic secondary amino groups and the C-2 hydroxy group of the sugar moiety in a meridional mode, resulting in a Λ-C2-helical configuration around the metal centre. The sugar rings adopt an unusual α-1C4 chair conformation and the sugar–chelate ring conformation is δ. The co-ordination behavior of D-ribose was confirmed by an X-ray analysis of an analogous compound, [Ni(D-Rib-men)2]Br2·2CH3OH 5 [D-Rib-men = 1-methylamino-2-(N-D-ribosyl)aminoethane], derived from the reaction of [Ni(men)3]Br2 with D-ribose [men = 1-amino-2-(N-methylamino)ethane]. The D-ribose moiety forms an α-N-glycosidic bond with the primary amino group of men, and adopts an α-4C1 chair form, the sugar–chelate ring conformation being δ. The CD spectra of 1–4 were measured in the region 9000–50 000 cm–1 and clearly indicated the structural features of the complexes; the Cotton effects at around 10 000 cm–1 (the first absorption band of the d–d transitions) reflected the conformation of the sugar chelate or the absolute configuration of the N-glycosidic nitrogen atom, and those at around 40 000–46 000 cm–1 (charge-transfer bands) demonstrated the C2 chiral configuration around the metal centre. These assignments were also confirmed by the CD spectra of known compounds.

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