Intermolecular interactions of punicin derivatives |
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Authors: | Marcel Albrecht Andreas Schmidt |
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Affiliation: | a Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany b Clausthal University of Technology, Institute of Inorganic Chemistry, Paul-Ernst-Strasse 4, D-38678 Clausthal-Zellerfeld, Germany |
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Abstract: | The 2- and 4-methyl derivates of punicin [N-(2′,5′-dihydroxyphenyl)-pyridinium chloride] were subjected to Knoevenagel reactions. Starting materials as well as reaction products were examined with respect to homo and hetero-intermolecular interactions. It was found that N-(2′,5′-dihydroxyphenyl)-2-methylpyridinium chloride forms a stable 2:1 complex to hydroquinone. Decomplexation can be accomplished by anion exchange to tetraphenylborate, or by competing complexation with p-benzoquinone. Results of three single crystal X-ray analyses as well as NMR titrations and dilution experiments are presented. |
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Keywords: | Pyridinium-phenolate NMR titration π-Complex Quinhydrone |
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