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Coordination Chemistry of Lipoic Acid and Related Compounds V [1]. New Heteroditopic Ligands Derived from Monoazacrown Ethers and Lipoic Acid
Authors:Michaela Wilhelm  Eva Berssen  Rainer Koch  Henry Strasdeit
Institution:(1) Department of Chemistry, University of Oldenburg, D-26129 Oldenburg, Germany, DE
Abstract:Summary.  Lipoyl imidazolide reacts with aza-15-crown-5 (1,4,7,10-tetraoxa-13-azacyclopentadecane) or aza-18-crown-6 (1,4,7,10,13-pentaoxa-16-azacyclooctadecane) to afford new N-lipoylated azacrown compounds in good yields. These compounds can be transformed into 1,3-dithiols and amines by reduction with complex hydrides of the disulfide and/or amide group of the lipoyl chain. The new pendant-arm macrocycles react as heteroditopic ligands by forming dithiolate and disulfide complexes with the ‘soft’ metal ions Ni2+ and Pd2+, respectively, and an amine complex with the ‘hard’ Li+ ion. Semiempirical and DFT calculations on the complexation of a lithium ion give a most favourable structure in which the azacrown and two solvent molecules are in contact with the metal but not the pendant arm. Received January 29, 2002; accepted (revised) March 25, 2002
Keywords:, ,Complexation, Crown compounds, Lipoic acid, Lithium, Quantum chemical calculations,
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