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The thiourea hydrogen bonds to the nitro group and stabilizes the incoming negative charge, while the amine acts a specific base to activate the nucleophile. This is an example of bifunctional catalysis. Hydrogen-bond catalysis is a type of organocatalysis that relies on use of hydrogen bonding interactions to accelerate and control organic ...
A squaramide organocatalyst typically contains the squaramide group and a hydrogen bond donor which is usually a tertiary amine group. The 3,5-bis(trifluoromethyl)phenyl-group is commonly used for the R group. For enantioselective squaramide catalysis, chirality is induced via the tertiary amine group. There are cases where both sides of the ...
Hydrogen-bonding between thiourea derivatives and carbonyl substrates involve two hydrogen bonds provided by coplanar amino substituents in the (thio)urea. [2] [3] [4][5] Squaramide catalysts engage in double H-bonding interactions and are often superior to thioureas.
The structure also reveals how two invariant residues, G-12 and G-8, are positioned within the active site consistent with their previously proposed role in acid/base catalysis. G12 is within hydrogen bonding distance to the 2’–O of C17, the nucleophile in the cleavage reaction, and the ribose of G8 hydrogen bonds to the leaving group 5 ...
Researchers have since conducted increasingly detailed investigations of the triad's exact catalytic mechanism. Of particular contention in the 1990s and 2000s was whether low-barrier hydrogen bonding contributed to catalysis, [18] [19] [20] or whether ordinary hydrogen bonding is sufficient to explain the mechanism.
In organic chemistry and organometallic chemistry, carbon–hydrogen bond activation (C−H activation) is a type of organic reaction in which a carbon–hydrogen bond is cleaved and replaced with a C−X bond (X ≠ H is typically a main group element, like carbon, oxygen, or nitrogen).
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With rare exceptions, H 2 is unreactive toward organic compounds in the absence of metal catalysts. The unsaturated substrate is chemisorbed onto the catalyst, with most sites covered by the substrate. In heterogeneous catalysts, hydrogen forms surface hydrides (M-H) from which hydrogens can be transferred to the chemisorbed substrate.