The synthesis and complexation study of some novel 3-methoxyphenyl chromenone crown ethers using conductometry |
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| Affiliation: | 1. University of Marmara, Department of Chemistry, Kad?köy, 81040 ?stanbul, Turkey;2. University of Bal?kesir, Department of Chemistry, 10100 Bal?kesir, Turkey;1. UG & PG Department of Physics, Karnatak Science College, Dharwad 580001, Karnataka, India;2. CGEPA, Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India;1. Department of Human Health and Nutrition, Shokei Gakuin University, 4-10-1, Yurigaoka, Natori, Miyagi 981-1295, Japan;2. Department of Food Technology, Industrial Technology Center, Gifu Prefectural Government, 47 Kitaoyobi, Kasamatsu-cho, Hashima-gun, Gifu 501-6064, Japan;3. Department of Health and Nutrition, Faculty of Psychological & Physical Science, Aichi Gakuin University, 12, Araike, Iwasaki-cho, Nisshin, Aichi 470-0195, Japan;1. Y?ld?z Technical University, Department of Chemistry, 34220 ?stanbul, Turkey;2. Y?ld?z Technical University, Department of Physics, 34220 ?stanbul, Turkey;1. Laboratório de Filmes Poliméricos e Nanotecnologia, Instituto de Química, Universidade Federal de Uberlândia, Uberlândia, Minas Gerais, Brazil;2. Instituto de Ciências Exatas, Naturais e Educação, Universidade Federal do Triângulo Mineiro, Uberaba, Minas Gerais, Brazil;3. Instituto de Genética e Bioquímica, Universidade Federal de Uberlândia, Uberlândia, Minas Gerais 38400-902, Brazil;4. Instituto de Ciências Biológicas e Naturais, Universidade Federal do Triângulo Mineiro, Praça Manoel Terra, 330, 38015-050 Uberaba, Minas Gerais, Brazil |
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| Abstract: | 7,8-Dihydroxy-3-(3,4-dimethoxyphenyl)-2H-chromenones, 7,8-dihydroxy-3-(3,5-dimethoxyphenyl)-2H-chromenones and 7,8-dihydroxy-3-(3,4,5-trimethoxyphenyl)-2H-chromenones, o-dihydroxy-3-methoxyphenylcoumarins, were prepared from 2,3,4-trihydroxybenzaldehyde and corresponding methoxyphenylacetic acid in NaOAc/Ac2O, respectively. 3-Methoxyphenyl-7,8-dihydroxy-2H-chromenone reacted with the polyethylene glycol ditosylate or dichloride in CH3CN/alkali carbonate to afford 12]crown-4, 15]crown-5 and 18]crown-6-chromonones.The chromatographically purified novel chromenone crown ethers were identified with IR, 1H NMR, 13C NMR and low and high resolution mass spectroscopy and elemental analysis.Stability constants for the 1:1 complexes of Na+ and K+ with different substituted methoxyphenyl derivatives of coumarino12]crown-4, coumarino15]crown-5 and coumarino18]crown-6 (5a–5i) have been determined by conductometry at 25 °C in a binary solvent, dioxane/water. For all the coumarino crown ether derivatives, the stability constant decreases for K+ ion compared to Na+ ion.The selectivity sequence of these crown ethers in dioxane/water has showed an irregular order with respect to their cavity size. |
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