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

Xiao Han; Richmond Lee; Tao Chen; Jie Luo; Yixin Lu; Kuo-Wei Huang

doi:10.1038/srep02557

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

Xiao Han, Richmond Lee, Tao Chen, Jie Luo, Yixin Lu, Kuo-Wei Huang

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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.

Original language	English (US)
Journal	Scientific Reports
Volume	3
Issue number	1
DOIs	https://doi.org/10.1038/srep02557
State	Published - Aug 30 2013

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https://repository.kaust.edu.sa/bitstream/10754/325391/1/Article-Scientific-Kinetic_ev-2013.pdf

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title = "Kinetic evidence of an apparent negative activation enthalpy in an organocatalytic process",

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.",

author = "Xiao Han and Richmond Lee and Tao Chen and Jie Luo and Yixin Lu and Kuo-Wei Huang",

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AU - Han, Xiao

AU - Lee, Richmond

AU - Chen, Tao

AU - Luo, Jie

AU - Lu, Yixin

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2013/8/30

Y1 - 2013/8/30

N2 - 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.

AB - 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.

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UR - http://www.nature.com/articles/srep02557

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

Abstract

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