The phenolic oxygen of ?-ICD was shown to be important in the reaction, implying the function of Bronsted acid moiety . ?-ICD and its related versions are effective catalysts for various other substrates.
12.
In fact, in vitro manipulation has shown that Bronsted acid-base catalyst, donating a proton to the displaced hydroxyl group on C-1 of the glucoside ( Schwarz, Brecker, and Nidetzky 2007 ).
13.
However, I can't find a reliable source ( searching for " pKa of hydrogen " infuriatingly reveals all sorts of irrelevant results, like the pKa of hydrogen sufide, hydrogen fluoride, basically every Bronsted acid ).
14.
Inspired by enzymes with deep active site pocket, List and coworkers designed and constructed a set of confined Bronsted acids with an extremely sterically demanding chiral pocket based on a C 2-symmetric bis ( binapthyl ) imidodiphosphoric acid.
15.
For example, chiral phosphines containing a Lewis base, a Bronsted acid, and an acid-activated Bronsted base were developed for an asymmetric aza-MBH reaction ( 86-96 % yield, 79-92 % ee ).
16.
If either the Bronsted acid or the Lewis base could be appropriately positioned on a chiral molecule, the Lewis base would react with the substrate ( Michael addition ), while the acid in an asymmetric environment would allow the chiral proton transfer.
17.
The Proton article in the section " Interaction of free protons with ordinary matter " says that such protons might combine with another atom or molecule to make " Bronsted acids, " which makes the " acrid " scent in the dream plausible.
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