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Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state |
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| Authors: | Gábor Kerti Anikó Borbás András Lipták Zita Illyés-Tünde Sándor Antus Masayuki Watanabe Gennaro Pescitelli |
| Institution: | a Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary b Research Group for Carbohydrates of the Hungarian Academy of Sciences, University of Debrecen, PO Box 55, H-4010 Debrecen, Hungary c Institute of Physical Chemistry, University of Debrecen, PO Box 7, H-4010 Debrecen, Hungary d JASCO Corporation, Hachioji-shi, Tokyo 192-85387, Japan e Università di Pisa, Dipartimento di Chimica e Chimica Industriale, via Risorgimento 35, 56126 Pisa, Italy |
| Abstract: | 1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl α-l-rhamnopyranoside and β-d-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs. |
| Keywords: | Solid-state CD Intra- and intermolecular exciton-coupled interactions 1- and 2-Naphthyl chromophores |
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