Hydrogen-Bonding-Assisted Ketimine Formation of Benzophenone Derivatives

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The favorable effect of 2-hydroxyphenyl groups for ketimine formation with benzophenone was demonstrated by combining computational and experimental studies. Although direct imine formation between benzophenone and primary amines is challenging, 2-hydroxybenzophenone or 2,2'-dihydroxybenzophenone was readily used for ketimine formation with various primary alkyl amines and anilines. Measured activation parameters and calculated energy profiles indicated that the 2-hydroxyphenyl group can lower both activation barriers and equilibrium energies by establishing intra-molecular and intermolecular hydrogen-bonding interactions.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-12
Language
English
Article Type
Article
Citation

JOURNAL OF ORGANIC CHEMISTRY, v.83, no.23, pp.14300 - 14306

ISSN
0022-3263
DOI
10.1021/acs.joc.8b01908
URI
http://hdl.handle.net/10203/249004
Appears in Collection
CH-Journal Papers(저널논문)
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