Investigating cyclic sotolon,maple furanone and their dimers in solution using optical rotation,electronic circular dichroism and vibrational circular dichroism |
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Authors: | Qin Yang Miao-Miao Liang Hui-Jun Wang Qi-Qi Zhao Hua-Jie Zhu Li Liu Charles U. Pittman |
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Affiliation: | 1. Chinese Center for Chirality, College of Pharmacy, Hebei University, Hebei, China;2. Department of Chemistry, Mississippi State University, MS, 39763, USA |
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Abstract: | The experimental optical rotation (OR), electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra of (R)-3-hydroxy-4,5-dimethylfuran-2(5H)-one (sotolon, 1) and (R)-5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one (maple furanone, 2) taken in chloroform were compared to their spectra calculated with time-dependent density functional theory (TDDFT). Sotolon was shown to exist as a dimer in chloroform while maple furanone remains a monomer. Transition state barriers for the enol/keto tautomerization of sotolon were calculated and found to be high. The VCD method offers promise to ultimately distinguish between the presence of monomers or dimers. |
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Keywords: | Dimer Sotolon Maple furanone Chiroptical spectroscopy |
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