Optical Resolution of a Co(III) Complex of 2-Hydroxy-1,3-propanediamine-N,N,N′,N′-tetraacetic Acid: Crystal Structure of (+)589-Strychnine (2-Hydroxy-1,3-propanediamine-N,N,N′,N′-tetraacetato)cobaltate(III) Sesquihydrate, (+)589-(STC)[Co(dhpta)]·1.5H2O
- 1 December 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 62 (12) , 3932-3938
- https://doi.org/10.1246/bcsj.62.3932
Abstract
The 2-hydroxy-1,3-propanediamine-N,N,N′,N′-tetraacetatocobaltate(III) complex has been optically resolved using strychnine nitrate. The crystal structure of the optically active complex with the resolving agent, (+)589-(STC)[Co(dhpta)]·1.5H2O has been determined from three dimensional X-ray diffraction data. The absolute configuration around the cobalt atom, to which two nitrogen and four oxygen atoms in the ligand are bonded nearly octahedrally, is Δ. The six-membered chelate ring adopts the λ-skew boat conformation. The intermolecular hydrogen bonding between the coordinated oxygen atom of the acetate ring and the protonated nitrogen atom of strychnine, which is one of the asymmetric centers, plays an important role in the diastereomeric discrimination. In contrast, the non-coordinated hydroxyl group in the complex ion does not interact directly with the strychnine molecule. The relationship between the absolute configuration around the cobalt center and the circular dichroism has been examined for the optically active complex ion.Keywords
This publication has 14 references indexed in Scilit:
- Structural Study of Optical Resolution. VI. The Crystal Structure of (+)589-cis-Chloroamminebis(ethylenediamine)cobalt(III) d-3-Bromocamphor-9-sulfonate MonohydrateBulletin of the Chemical Society of Japan, 1978
- The crystal and molecular structure of potassium 2-hydroxy-1,3-propanediamine-N,N,N',N'-tetraacetatocobaltateCollection of Czechoslovak Chemical Communications, 1978
- The crystal structure of potassium (−)546-trimethylenediaminetetraacetatocobaltate(III) dihydrateActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1972
- Stereochemistry of Trimethylenediaminetetraacetatocobaltate(III)Bulletin of the Chemical Society of Japan, 1970
- Stereospecific Influences in Metal Complexes Containing Optically Active Ligands.1 Part V. Absolute Stereospecificity in Metal Complexes of Optically Active Polyaminocarboxylic AcidsJournal of the American Chemical Society, 1961
- The Preparation of 1,2-Propylenediaminetetraacetic Acid and its Resolution through the Cobalt(III) ComplexJournal of the American Chemical Society, 1959
- The Structures of Ammonium and Rubidium Ethylenediaminetetraacetatocobaltate(III)1Journal of the American Chemical Society, 1959
- The Resolution of the Quinquedentate Cobalt(III) Complexes with Ethylenediaminetetraacetic AcidJournal of the American Chemical Society, 1958
- The Resolution and Racemization of Potassium Ethylenediaminetetra-acetatocobaltate(III)The Journal of Physical Chemistry, 1955
- The Stereochemistry of Complex Inorganic Compounds. XVII. The Stereochemistry of Hexadentate Ethylenediaminetetraacetic Acid ComplexesJournal of the American Chemical Society, 1953