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Role of Hydrogen‐Bonding Acceptors in Organo‐Enamine Catalysis
Author(s) -
Han Junbin,
Lu Zhichao,
Flach Andrew L.,
Paton Robert S.,
Hammond Gerald B.,
Xu Bo
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502407
Subject(s) - enamine , catalysis , protonation , chemistry , hydrogen bond , catalytic cycle , hydrogen , acceptor , quantum chemical , photochemistry , organocatalysis , computational chemistry , organic chemistry , molecule , enantioselective synthesis , ion , physics , condensed matter physics
A hydrogen bond acceptor plays an important role in the catalytic cycle of organo‐enamine catalysis. It can effectively influence the rate of reaction through hydrogen bonding interaction with enammonium (N‐protonated enamine intermediate). Our findings are supported by both kinetic experiments and quantum chemical calculations.