About Underappreciated Yet Active Conformations of
Thiourea Organocatalysts
Version 2 2017-12-14, 18:20
Version 1 2017-08-08, 12:53
Posted on 2017-12-14 - 18:20
Conformational dynamics
can define the function of organocatalysts. While the accepted mechanism
of Schreiner’s catalyst features a double hydrogen bond to
the substrate that only forms with the anti-anti conformation
of its central thiourea group, our electronic-structure theory study
reveals that binding of the model substrate methyl vinyl ketone prefers syn-anti conformations. We find a new mechanism featuring
π stacking interactions and highlight the need for extensive
structure searches for flexible molecules, especially when aiming
for structure-based design of catalytic activity.
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Supady, Adriana; Hecht, Stefan; Baldauf, Carsten (2017). About Underappreciated Yet Active Conformations of
Thiourea Organocatalysts. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01782
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AUTHORS (3)
AS
Adriana Supady
SH
Stefan Hecht
CB
Carsten Baldauf
KEYWORDS
moleculeelectronic-structure theory studyThiourea Organocatalysts Conformational dynamicsActive Conformationsmechanismsyn-anti conformationsstructure searchesfunctionSchreinerbindingthiourea groupstructure-based designanti-anti conformationinteractionmodel substrate methyl vinyl ketonehydrogen bondorganocatalystUnderappreciated