Mechanistic study of the Soai autocatalytic reaction informed by kinetic analysis |
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| Institution: | 1. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong;2. Department of Chemistry, Faculty of Science, Kyoto University, Japan;1. MTA-DE Homogeneous Catalysis and Reaction Mechanisms Research Group, H-4010 Debrecen, POB 7, Hungary;2. Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, POB 20, Hungary;3. Department of Physical Chemistry, University of Debrecen, H-4010 Debrecen, POB 7, Hungary;1. Tianjin Key Laboratory for Modern Drag Delivery & High Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, PR China;2. Tianjin Key Laboratory of Chemistry and Analysis of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, PR China;3. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China;4. Tianjin Key Laboratory of Industry Microbiology, College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, PR China |
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| Abstract: | Detailed kinetic studies of the Soai reaction affirm the basic mechanistic picture previously developed in kinetic, spectroscopic and molecular modelling studies, and also suggest that refinements to the proposed elementary reaction steps must be considered. The alkanol reaction product is driven strongly and without bias towards the formation of homochiral and heterochiral dimers. The reaction is catalyzed by only the homochiral dimers. Consideration of the kinetic profiles from reactions carried out with different initial dialkylzinc concentrations support a proposal for a tetrameric transition state, but further experimental work is required to delineate the nature of this species. The power of reaction calorimetry as a kinetic tool for discerning subtle effects of the shape of the kinetic profile is highlighted. The importance of combining kinetic evidence with spectroscopic and other characterization tools is emphasized. |
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