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Inframolecular Protonation Process of Norbadione A:  Influence of the Ionic Environment and Stereochemical Consequences

Publié dansJournal of the American Chemical Society, vol. 127, no. 4, p. 1323-1333
Date de publication2005
Résumé

The microscopic protonation mechanism, at an inframolecular level, of norbadione A, a pigment extracted from mushrooms and known to complex cesium cations, was determined by using 1H NMR titrations and the cluster expansion method. This study revealed a pH dependent Z to E isomer switch that occurs in both pulvinic moieties. As a consequence, norbadione A can exist in solution in four stereomeric forms (E−E, E−Z, Z−E, and Z−Z), which can be of interest in the development of molecular-level devices. In the presence of 0.15 M NaCl, the calculated microconstants showed an unusual apparent cooperativity between the enol groups, which results from the release of the sodium cations upon protonation of norbadione A.

Citation (format ISO)
KUAD, Paul et al. Inframolecular Protonation Process of Norbadione A:  Influence of the Ionic Environment and Stereochemical Consequences. In: Journal of the American Chemical Society, 2005, vol. 127, n° 4, p. 1323–1333. doi: 10.1021/ja0483185
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ISSN du journal0002-7863
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