NDLI: Galactose oxidase models: insights from <sup>19</sup>F NMR spectroscopy

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Galactose oxidase models: insights from ¹⁹F NMR spectroscopy

Content Provider	Royal Society of Chemistry (RSC)
Author	Valle, Carlos Perez Del Philouze, Christian Saint-Aman, Eric Thomas, Fabrice Hamman, Sylvain Michel, Fabien
Copyright Year	2009
Abstract	19F labelled tripodal ligands that possess a N3O donor set (one phenol, one tertiary amine and either two pyridines or one pyridine and one quinoline) have been synthesized. The fluorine is incorporated either at the phenol O-donor (HLF and HLCF3) or at the quinoline N-donor (HLqOMe and HLqNO2). The copper(II)–phenol complexes (2H)2+, (1H)2+, (3H)2+ and (4H)2+ as well as the corresponding copper(II)–phenolate complexes have been characterized. X-Ray diffraction reveals an increase in the oxygen–copper bond distance of more than 0.4 Å upon protonation of the phenolate moiety of (4)+. Protonation is accompanied by an axial to equatorial isomerization of the quinoline group. DFT calculations show that stretching of the Cu–O(phenol) bond, π-stacking interactions and rotation of the pyridine are key steps in this isomerization process. Protonation, and thus changes in the oxygen–copper bond distance induce either a decrease ((1H)2+, (2H)2+) or an increase ((3H)2+ and (4H)2+) in the copper–fluorine distance that could be monitored by 19F NMR. In the former case, a broadening of the 19F NMR signal is observed, whereas a sharpening is observed in the latter case. Temperature dependent 19F NMR measurements on equimolar mixtures of the phenol and phenolate complexes of (3)+ and (4)+ reveal rate constants for proton transfer and/or isomerization of 3000 ± 100 s−1 and 2900 ± 100 s−1, respectively, at the coalescence temperature. This temperature was found to be strongly affected by the phenolpara-substituent as it is 226 K and ca. 330 K for (3)+ and (4)+, respectively. A phenoxyl radical species ((3˙)2+) could be generated and characterized for the first time by 19F NMR spectroscopy.
Starting Page	832
Ending Page	842
Page Count	11
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	5
Journal	Dalton Transactions
DOI	10.1039/b813036a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Fluorine-19 nuclear magnetic resonance Phenol Amine Pyridine Quinoline Fluorine Copper X-ray scattering techniques Chemical bond Isomerization Nuclear magnetic resonance Hydrogen Alkoxy group Nuclear magnetic resonance spectroscopy
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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