Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/24960
Title: Hydrogen bond donor-acceptor-donor organocatalysis for conjugate addition of benzylidene barbiturates via complementary DAD-ADA hydrogen bonding
Authors: Leung, FKC
Cui, JF
Hui, TW
Zhou, ZY
Wong, MK 
Issue Date: 2014
Publisher: Royal Society of Chemistry
Source: RSC advances, 2014, v. 4, no. 51, p. 26748-26756 How to cite?
Journal: RSC Advances 
Abstract: A new class of hydrogen bond donor-acceptor-donor (HB-DAD) organocatalysts has been developed for conjugate addition of benzylidene barbiturates. HB-DAD organocatalyst 1a (featuring para-chloro-pyrimidine as the hydrogen bond acceptor (HBA), N-H as the hydrogen bond donor (HBD) and a trifluoroacetyl group as the electron withdrawing group (EWG)) is able to activate benzylidene barbiturates through complementary DAD-ADA hydrogen bonding. Using 1a in benzylidene barbiturate conjugate addition, good yields were achieved. The relative rate constant (krel = 2.9) of 1a in catalyzing the conjugate addition of benzylidene barbiturates and the binding constant (KA = 8936 (±723) M-1) of 1a with benzylidene barbiturates were determined by NMR and UV/Vis. spectroscopy studies. The excellent correlation (R2 = 0.97) between the relative rate constant and binding affinity of 1a with benzylidene barbiturates provides support for the importance of DAD-ADA hydrogen bonding in organocatalysis.
URI: http://hdl.handle.net/10397/24960
ISSN: 2046-2069
DOI: 10.1039/c4ra04020a
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