Recognition of caffeine by a water-soluble acyclic phane compound |
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| Authors: | Nobuyuki Hayashi Tomomi Ujihara Shigeki Jin |
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| Institution: | 1. National Food Research Institute, National Agriculture and Food Research Organization (NARO), 2-1-12 Kannondai, Tsukuba, Ibaraki 305-8642, Japan;2. National Institute of Vegetable and Tea Science, National Agriculture and Food Research Organization (NARO), 2769 Kanaya, Shimada, Shizuoka 428-8501, Japan;3. Faculty of Health Science, Hokkaido University, Kita 12, Nishi 5, Kita-ku, Sapporo, Hokkaido 060-0812, Japan |
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| Abstract: | Caffeine (1,3,7-trimethylxanthine) is a chemical substance associated with everyday human life. In order to recognize caffeine in water, six water-soluble acyclic phane compounds composed of three aromatic rings were examined as artificial receptors. 1H NMR titration experiments revealed that 6,6′-1,3-phenylenebis(carbonylimino)]bis-1,3-naphthalenedisulfonate had the highest binding ability for caffeine, with a binding constant (Kb) of 127±5 M−1 at 300 K. While this phane compound also formed a complex with theophylline (1,3-dimethylxanthine) at around half the value of the binding constant for caffeine (Kb=64±4 M−1), it showed weak or little complexation for adenosine, guanosine, inosine, and their 5′-phosphates (sodium salts of adenylic acid, guanylic acid, and inosinic acid). |
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| Keywords: | Acyclic phane compound Complexation Caffeine Theophylline Nucleosides Nucleotides |
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