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Literature DB >> 23025278

Racing carbon atoms. Atomic motion reaction coordinates and structural effects on Newtonian kinetic isotope effects.

Ivonne L Andujar-De Sanctis¹, Daniel A Singleton.

Abstract

Intramolecular (13)C kinetic isotope effects were determined for the dimerization of methacrolein. Trajectory studies accurately predict the isotope effects and support an origin in Newton's second law of motion, with no involvement of zero-point energy or transition state recrossing. Atomic motion reaction coordinate diagrams are introduced as a way to qualitatively understand the selectivity.

Entities: Chemical Disease

Mesh：

Substances：
Carbon Isotopes
Carbon

Year: 2012 PMID： 23025278 PMCID： PMC3490209 DOI： 10.1021/ol302389f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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References

14 in total

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Authors: Pierluigi Caramella; Paolo Quadrelli; Lucio Toma
Journal: J Am Chem Soc Date: 2002-02-20 Impact factor: 15.419

2. A new form of kinetic isotope effect. Dynamic effects on isotopic selectivity and regioselectivity.

Authors: Daniel A Singleton; Chao Hang; Michael J Szymanski; Erin E Greenwald
Journal: J Am Chem Soc Date: 2003-02-05 Impact factor: 15.419

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Authors: Tefsit Bekele; Chad F Christian; Mark A Lipton; Daniel A Singleton
Journal: J Am Chem Soc Date: 2005-06-29 Impact factor: 15.419

4. Computational study on the reaction pathway of α-bromoacetophenones with hydroxide ion: possible path bifurcation in the addition/substitution mechanism.

Authors: Shuhei Itoh; Nobuyoshi Yoshimura; Makoto Sato; Hiroshi Yamataka
Journal: J Org Chem Date: 2011-09-07 Impact factor: 4.354

5. Entropic intermediates and hidden rate-limiting steps in seemingly concerted cycloadditions. Observation, prediction, and origin of an isotope effect on recrossing.

Authors: Ollie M Gonzalez-James; Eugene E Kwan; Daniel A Singleton
Journal: J Am Chem Soc Date: 2012-01-18 Impact factor: 15.419

6. The need for enzymatic steering in abietic acid biosynthesis: gas-phase chemical dynamics simulations of carbocation rearrangements on a bifurcating potential energy surface.

Authors: Matthew R Siebert; Jiaxu Zhang; Srirangam V Addepalli; Dean J Tantillo; William L Hase
Journal: J Am Chem Soc Date: 2011-05-06 Impact factor: 15.419

Racing carbon atoms. Atomic motion reaction coordinates and structural effects on Newtonian kinetic isotope effects.

1. An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene.

2. A new form of kinetic isotope effect. Dynamic effects on isotopic selectivity and regioselectivity.

3. "Concerted" transition state, stepwise mechanism. Dynamics effects in C2-C6 enyne allene cyclizations.

4. Computational study on the reaction pathway of α-bromoacetophenones with hydroxide ion: possible path bifurcation in the addition/substitution mechanism.

5. Entropic intermediates and hidden rate-limiting steps in seemingly concerted cycloadditions. Observation, prediction, and origin of an isotope effect on recrossing.

6. The need for enzymatic steering in abietic acid biosynthesis: gas-phase chemical dynamics simulations of carbocation rearrangements on a bifurcating potential energy surface.

7. Sequential transition States and the valley-ridge inflection point in the formation of a semibullvalene.

8. Recrossing and dynamic matching effects on selectivity in a Diels-Alder reaction.

9. Control elements in dynamically determined selectivity on a bifurcating surface.

10. Newtonian kinetic isotope effects. Observation, prediction, and origin of heavy-atom dynamic isotope effects.