Kinetic evidence of an apparent negative activation enthalpy in an organocatalytic process

Handle URI:
http://hdl.handle.net/10754/325391
Title:
Kinetic evidence of an apparent negative activation enthalpy in an organocatalytic process
Authors:
Han, Xiao; Lee, Richmond; Chen, Tao; Luo, Jie; Lu, Yixin; Huang, Kuo-Wei ( 0000-0002-8506-3566 )
Abstract:
A combined kinetic and computational study on our tryptophan-based bifunctional thiourea catalyzed asymmetric Mannich reactions reveals an apparent negative activation enthalpy. The formation of the pre-transition state complex has been unambiguously confirmed and these observations provide an experimental support for the formation of multiple hydrogen bonding network between the substrates and the catalyst. Such interactions allow the creation of a binding cavity, a key factor to install high enantioselectivity.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Han X, Lee R, Chen T, Luo J, Lu Y, et al. (2013) Kinetic Evidence of an Apparent Negative Activation Enthalpy in an Organocatalytic Process. Sci Rep 3. doi:10.1038/srep02557.
Publisher:
Nature Publishing Group
Journal:
Scientific Reports
Issue Date:
30-Aug-2013
DOI:
10.1038/srep02557
PubMed ID:
23990028
PubMed Central ID:
PMC3757351
Type:
Article
ISSN:
20452322
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorHan, Xiaoen
dc.contributor.authorLee, Richmonden
dc.contributor.authorChen, Taoen
dc.contributor.authorLuo, Jieen
dc.contributor.authorLu, Yixinen
dc.contributor.authorHuang, Kuo-Weien
dc.date.accessioned2014-08-27T09:50:26Z-
dc.date.available2014-08-27T09:50:26Z-
dc.date.issued2013-8-30en
dc.identifier.citationHan X, Lee R, Chen T, Luo J, Lu Y, et al. (2013) Kinetic Evidence of an Apparent Negative Activation Enthalpy in an Organocatalytic Process. Sci Rep 3. doi:10.1038/srep02557.en
dc.identifier.issn20452322en
dc.identifier.pmid23990028en
dc.identifier.doi10.1038/srep02557en
dc.identifier.urihttp://hdl.handle.net/10754/325391en
dc.description.abstractA combined kinetic and computational study on our tryptophan-based bifunctional thiourea catalyzed asymmetric Mannich reactions reveals an apparent negative activation enthalpy. The formation of the pre-transition state complex has been unambiguously confirmed and these observations provide an experimental support for the formation of multiple hydrogen bonding network between the substrates and the catalyst. Such interactions allow the creation of a binding cavity, a key factor to install high enantioselectivity.en
dc.language.isoenen
dc.publisherNature Publishing Groupen
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. To view a copy of this license, visit http://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectthioureaen
dc.subjecttryptophanen
dc.subjectbinding siteen
dc.subjectcatalysisen
dc.subjectchemical modelen
dc.subjectchemistryen
dc.subjectcomputer simulationen
dc.subjectenergy transferen
dc.subjectentropyen
dc.subjecthydrogen bonden
dc.subjectkineticsen
dc.subjectprotein bindingen
dc.subjectBinding Sitesen
dc.subjectCatalysisen
dc.subjectComputer Simulationen
dc.subjectEnergy Transferen
dc.subjectEntropyen
dc.subjectHydrogen Bondingen
dc.subjectKineticsen
dc.subjectModels, Chemicalen
dc.subjectProtein Bindingen
dc.subjectThioureaen
dc.subjectTryptophanen
dc.titleKinetic evidence of an apparent negative activation enthalpy in an organocatalytic processen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalScientific Reportsen
dc.identifier.pmcidPMC3757351en
dc.eprint.versionPublisher's Version/PDFen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singaporeen
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)en
kaust.authorHan, Xiaoen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien
kaust.authorChen, Taoen
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