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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Multifaceted Stereoselectivity in Polyatomic Reactions.

Huilin Pan1, Fengyan Wang2, Kopin Liu3,4,5

  • 1Southern University of Science and Technology, Shenzhen, P. R. China 518055.

The Journal of Physical Chemistry. A
|July 8, 2020
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Summary
This summary is machine-generated.

This study explores stereoselectivity in chemical reactions by experimentally aligning polyatomic molecules. Comparing different reactant orientations reveals deeper insights into reaction dynamics and mechanisms.

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Area of Science:

  • Chemical Kinetics
  • Molecular Dynamics
  • Physical Chemistry

Background:

  • Stereoselectivity enhances chemical reactivity through reactant alignment.
  • This concept is linked to the Arrhenius equation's A-factor and kinetic entropy.
  • Experimental studies on polyatomic molecules face significant challenges.

Purpose of the Study:

  • To experimentally investigate stereoselectivity in polyatomic reactions.
  • To understand the dynamical consequences and mechanistic origins of stereoselectivity.
  • To develop a more complete conceptual framework for complex chemical systems.

Main Methods:

  • Utilized two experimental approaches: state selection and laboratory alignment/orientation.
  • Applied both methods in parallel to the same polyatomic reaction system.
  • Compared results from symmetric-top (CHD3) and spherical-top (CH4) molecules.

Main Results:

  • Gained deeper physical insights into stereoselectivity by comparing experimental approaches.
  • Demonstrated the value of parallel experimental strategies for complex reactions.
  • Identified key differences and similarities between CHD3 and CH4 reactions.

Conclusions:

  • Experimental investigation of stereoselectivity in polyatomic reactions is feasible and insightful.
  • Parallel approaches provide a robust method for dissecting reaction dynamics.
  • Findings pave the way for studying more complex chemical systems and refining theoretical models.