Kinetic isotope and thermodynamic analysis of the nornicotine-catalyzed aqueous aldol reaction |
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| Affiliation: | 1. College of Pharmacy, Touro University-California, Vallejo, CA 94592, USA;2. Department of Basic Science, Touro University-California, Vallejo, CA 94592, USA;3. Department of Natural Science and Mathematics, Dominican University of California, San Rafael, CA 94901, USA;1. Department of Pharmacy and Biotechnology, Alma Mater Studiorum University of Bologna, Via Belmeloro, 6, 40126 Bologna, Italy;2. Department of Pharmacy and Biotechnology, Alma Mater Studiorum University of Bologna, Via S. Donato, 19/2, 40127 Bologna, Italy;3. National Institute of Biostructures and Biosystems, Via delle Medaglie D''oro, 305, 00136 Roma, Italy;4. Institute of Medical Microbiology and Immunobiology, Faculty of Medicine, University of Szeged, Szeged, Hungary;1. Peoples Friendship University of Russia, 6, Mikluho Maklaya St., Moscow 117198, Russia;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, B-334, Moscow 119991, Russia;3. Institute of Chemistry, Vietnam Academy of Science & Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;1. Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, PR China |
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| Abstract: | A series of kinetic isotope effects and thermodynamic studies were performed to test key predictions of a computationally derived model for a nornicotine-catalyzed aqueous aldol reaction. The relative energies of the two computationally-derived transition states were challenged using the proton inventory, which demonstrated that a single water molecule from the solvent is involved in, or before, the rate-limiting step. These results suggest the importance of proton transfer in the aqueous aldol reaction and may assist the development of other aqueous organocatalytic processes. |
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