"pKa" of calixarenes and analogs in nonaqueous solvents.
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概要
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The acid dissociation constants (<I>K</I><SUB>app</SUB>) of <I>p</I>-<I>t</I>-butylcalix[<I>n</I>]arenes (<B>1</B><I><SUB>n</SUB></I>: <I>n</I>=4, 6, and 8), <I>O</I>-methylated <I>p</I>-<I>t</I>-butylcalix[4]arene (<B>2</B>Me<I><SUB>n</SUB></I>), and their noncyclic analogs (<B>3</B><I><SUB>n</SUB></I>) were estimated in THF at 25°C. As pH indicators, Et<SUB>4</SUB>N<SUP>+</SUP> salts of <I>p</I>-nitrophenolate, 2,4-dinitrophenolate, and picrate were employed. The p<I>K</I><SUB>app</SUB> values for <B>1</B><I><SUB>n</SUB></I> were lowered by at least four p<I>K</I> units from that of <I>p</I>-<I>t</I>-butylphenol because of strong intramolecular hydrogen-bonding interactions. Compounds <B>2</B><I><SUB>n</SUB></I> involved both the strong and weak hydrogen bonds: the proton in the strong hydrogen bond showed the acidity comparable with that of <B>1</B><I><SUB>n</SUB></I> whereas that in the weak hydrogen bond showed the relatively high p<I>K</I><SUB>app</SUB>. These properties were discussed in relation to δ<SUB>OH</SUB> (chemical shift in <SUP>1</SUP>HNMR) and ν<SUB>OH</SUB>(OH vibration band in IR). This is the first systematic discussion on "p<I>K</I><SUB>a</SUB>" of <I>p</I>-<I>t</I>-butylcalix[<I>n</I>]arenes.
- 公益社団法人 日本化学会の論文
著者
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MATSUDA Tsutomu
Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa University
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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Iwamoto Koji
Department Of Organic Synthesis Faculty Of Engineering Kyushu University
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Araki Koji
Department Of Applied Chemistry Faculty Of Engineering Kyushu Institute Of Technology
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