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The Synthesis, Structure, and FTIR Spectroelectrochemistry of W(CO)5 Complexes of 4-Oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic and 5-Oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic Acids

The Synthesis, Structure, and FTIR Spectroelectrochemistry of W(CO)5 Complexes of 4-Oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic and 5-Oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic Acids

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KOWALSKI, Konrad, Rainer WINTER, Anna MAKAL, Aleksandra PAZIO, Krzysztof WOZNIAK, 2009. The Synthesis, Structure, and FTIR Spectroelectrochemistry of W(CO)5 Complexes of 4-Oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic and 5-Oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic Acids. In: European Journal of Inorganic Chemistry. 2009(27), pp. 4069-4077. ISSN 1434-1948

@article{Kowalski2009Synth-13793, title={The Synthesis, Structure, and FTIR Spectroelectrochemistry of W(CO)5 Complexes of 4-Oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic and 5-Oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic Acids}, year={2009}, doi={10.1002/ejic.200900347}, number={27}, volume={2009}, issn={1434-1948}, journal={European Journal of Inorganic Chemistry}, pages={4069--4077}, author={Kowalski, Konrad and Winter, Rainer and Makal, Anna and Pazio, Aleksandra and Wozniak, Krzysztof} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/13793"> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-06-21T12:10:34Z</dc:date> <dc:contributor>Winter, Rainer</dc:contributor> <dc:creator>Winter, Rainer</dc:creator> <dc:creator>Pazio, Aleksandra</dc:creator> <dc:rights>deposit-license</dc:rights> <dcterms:issued>2009</dcterms:issued> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/13793"/> <dc:contributor>Wozniak, Krzysztof</dc:contributor> <dcterms:bibliographicCitation>First publ. in: European Journal of Inorganic Chemistry (2009), 27, pp. 4069–4077</dcterms:bibliographicCitation> <dc:creator>Kowalski, Konrad</dc:creator> <dc:contributor>Kowalski, Konrad</dc:contributor> <dcterms:abstract xml:lang="eng">With the aim of developing new IR-detectable metal–carbonyl tracers for the amino function, we have synthesized W(CO)5 complexes of 4-oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic acid (2) and 5-oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic acid (3) by AlCl3-catalyzed Friedel–Crafts reaction of W(CO)5–2,5-dimethylazaferrocene (1) with succinic or glutaric anhydride. Complexes 2 and 3 are thermally stable and display sharp, intense absorption bands of tungsten-coordinated CO ligands at ca. 1923 cm–1. In the crystalline state, molecules of 2 and 3 are stabilized by a network of intra- and intermolecular hydrogen bonds, as shown by single-crystal X-ray structure analysis. Complex 2 was transformed into the corresponding N-succinimidyl ester 4. Its utility toward labeling of amino acids was tested in its reaction with glycine methyl ester. Corresponding glycine amide 5 was obtained in 82 % yield and is an air/thermally stable bioconjugate exhibiting intense sharp absorption bands of the W–CO reporting group at ca. 1923 cm–1. Cyclic voltammetry of 1, 2, 3, and acetyl derivative 6 shows the presence of two redox events in each case. The first redox couple is ascribed as an azaferrocene-centered oxidation–reduction, whereas the second, irreversible process at higher potential originates from a W(CO)5-centered oxidation. FTIR spectroelectrochemistry allowed us to monitor the spectroscopic changes accompanying the 1/1·+, 2/2·+, and 6/6·+ redox transformations. Significant W–CO absorption band shifts were recorded in the course of these experiments.</dcterms:abstract> <dcterms:title>The Synthesis, Structure, and FTIR Spectroelectrochemistry of W(CO)5 Complexes of 4-Oxo-4-(2,5-dimethylazaferrocen-1′-yl)butanoic and 5-Oxo-5-(2,5-dimethylazaferrocen-1′-yl)pentanoic Acids</dcterms:title> <dc:language>eng</dc:language> <dc:contributor>Makal, Anna</dc:contributor> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-06-21T12:10:34Z</dcterms:available> <dc:contributor>Pazio, Aleksandra</dc:contributor> <dcterms:rights rdf:resource="http://nbn-resolving.org/urn:nbn:de:bsz:352-20140905103605204-4002607-1"/> <dc:creator>Makal, Anna</dc:creator> <dc:creator>Wozniak, Krzysztof</dc:creator> </rdf:Description> </rdf:RDF>

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