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- W2113282679 endingPage "12469" @default.
- W2113282679 startingPage "12460" @default.
- W2113282679 abstract "Abstract A Morita–Baylis–Hillman (MBH) reaction catalyzed by thiourea was monitored by ESI‐MS(/MS) and key intermediates were intercepted and characterized. These intermediates suggest that thiourea acts as an organocatalyst in all steps of the MBH reaction cycle, including the rate‐limiting proton‐transfer step. DFT calculations, performed for a model MBH reaction between formaldehyde and acrolein with trimethylamine as base and in the presence or the absence of thiourea, suggest that thiourea accelerates MBH reactions by decreasing the transition‐state (TS) energies through bidentate hydrogen bonding throughout the whole catalytic cycle. In the rate‐limiting proton‐transfer step, the thiourea acts not as a proton shuttle, but as a Brønsted acid stabilizing the basic oxygen center that is formed in the TS." @default.
- W2113282679 created "2016-06-24" @default.
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- W2113282679 creator A5075838941 @default.
- W2113282679 creator A5078051461 @default.
- W2113282679 creator A5083294402 @default.
- W2113282679 date "2009-11-10" @default.
- W2113282679 modified "2023-10-18" @default.
- W2113282679 title "Brønsted Acid Catalyzed Morita-Baylis-Hillman Reaction: A New Mechanistic View for Thioureas Revealed by ESI-MS(/MS) Monitoring and DFT Calculations" @default.
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