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    Hydrophobic Control of Diastereoselectivity in the Synthesis of Double-Chain Surfactant Co(III) Complexes

    Year: 1998

    Journal: Langmuir 1998, 14, 2589-2592, 20111221

    Authors: David A. Jaeger,* Ven B. Reddy, Navamoney Arulsamy, D. Scott Bohle, David W. Grainger and B. Berggren

    Organizations: aDepartment of Chemistry, University of Wyoming, Laramie, Wyoming 82071 bDepartment of Chemistry, Colorado State University, Fort Collins, Colorado 80523

    A series of double-chain surfactant octahedral Co(III) complexes 1-4 has been prepared in both water and 20:1 (v/v) ethanol-water by the reaction of an N-alkylethylenediamine ligand (5) with sodium hexanitrocobaltate(III), followed by the addition of sodium perchlorate or sodium nitrate: trans-dinitrocisoid- bis(N-alkylethylenediamine)cobalt(III) perchlorate (1) and nitrate (3), and trans-dinitro-transoidbis( N-alkylethylenediamine)cobalt(III) perchlorate (2) and nitrate (4) (alkyl ) hexyl, octyl, decyl, dodecyl, and hexadecyl). The cisoid 1 (3)/transoid 2(4) diastereomer ratio increased on going from 20:1 ethanolwater to water, in particular by a factor of approximately 5 for the octyl and dodecyl perchlorate systems and approximately 8 for the hexadecyl perchlorate system. The increase in the relative amount of cisoid 1(3) is attributed to the hydrophobic effect associated with the aggregation of ligand 5 in water.