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Issue 51, 2014
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Hydrogen bond donor–acceptor–donor organocatalysis for conjugate addition of benzylidene barbiturates via complementary DAD–ADA hydrogen bonding

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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.

Graphical abstract: Hydrogen bond donor–acceptor–donor organocatalysis for conjugate addition of benzylidene barbiturates via complementary DAD–ADA hydrogen bonding

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Publication details

The article was received on 02 May 2014, accepted on 09 Jun 2014 and first published on 10 Jun 2014


Article type: Paper
DOI: 10.1039/C4RA04020A
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RSC Adv., 2014,4, 26748-26756

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    Hydrogen bond donor–acceptor–donor organocatalysis for conjugate addition of benzylidene barbiturates via complementary DAD–ADA hydrogen bonding

    F. K. Leung, J. Cui, T. Hui, Z. Zhou and M. Wong, RSC Adv., 2014, 4, 26748
    DOI: 10.1039/C4RA04020A

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