Coordination chemistry of lipoic acid and related compounds V. New heteroditopic ligands derived from monoazacrown ethers and lipoic acid

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 comp...

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Published inMonatshefte für Chemie Vol. 133; no. 8; pp. 1097 - 1108
Main Authors Wilhelm, M, Berssen, E, Koch, R, Strasdeit, H
Format Journal Article
LanguageEnglish
Published WIEN Springer Nature 01.08.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
COMPLEX
SELF-ASSEMBLED MONOLAYERS
RECOGNITION
AB-INITIO
PARAMETERS
lithium
LARIAT ETHERS
HELICAL PEPTIDES
quantum chemical calculations
crown compounds
OPTIMIZATION
lipoic acid
complexation
SPECTRA
SURFACES
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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.
ISSN:0026-9247
1434-4475
DOI:10.1007/s007060200080