Molecular mechanism of DCR phenomenon observed in (RS)-1-cyclohexylethylamine–mandelic acid resolution system |
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| Institution: | 2. Basic Medical Science and Molecular Medicine, Tokai University School of Medicine, Isehara, Kanagawa 259-1193, Japan;1. Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain;2. Instituto de Química-Física “Rocasolano” (CSIC), Serrano 119, 28006 Madrid, Spain;1. Biology Department, Faculty of Science, King Khalid University, 9004, Abha, Saudi Arabia;2. Faculty of Science, Zoology Department, Suez University, 43533, Suez, Egypt;3. Faculty of Science, Chemistry Department, Suez University, 43533, Suez, Egypt;1. Tissue Engineering Lab, Department of Bio-Mechatronic Engineering, College of Biotechnology and Bioengineering, Sungkyunkwan University, Suwon, Republic of Korea;2. Department of Physics and Photon Science, GIST, Gwang-ju, Republic of Korea |
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| Abstract: | In the resolution system of (RS)-1-cyclohexylethylamine (CHEA) with (S)-mandelic acid (MA), the DCR (dielectrically controlled resolution) phenomenon was clearly observed. (S)-CHEA and (R)-CHEA were obtained as less-soluble salts from 2-propanol (ε = 18) and water (ε = 78), respectively. Although (S)-MAs pack similarly in the crystals of both of the salts, the chiral spaces formed between the columns of (S)-MAs are significantly different in shape. The present study showed that these chiral spaces are crucial to molecular recognition and their shapes are greatly influenced by the dielectric property of the solvent employed. |
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