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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Barrierless Single-Electron-Induced cis-trans Isomerization.

Shachar Klaiman1, Lorenz S Cederbaum2

  • 1Theoretische Chemie, Physikalisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 229, 69120 Heidelberg (Germany). shachar.klaiman@pci.uni-heidelberg.de.

Angewandte Chemie (International Ed. in English)
|July 17, 2015
PubMed
Summary
This summary is machine-generated.

Electron attachment creates a barrierless pathway for maleonitrile cis-trans isomerization. This anionic activation method controls chemical reactions and isomer formation, with potential for broader applications.

Keywords:
anionscis-trans isomerizationelectron-driven reactionsexcited statesnitriles

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Area of Science:

  • Physical Chemistry
  • Chemical Reaction Dynamics
  • Computational Chemistry

Background:

  • Controlling chemical reactions often involves manipulating activation energy barriers.
  • Isomerization reactions, such as cis-trans isomerization, are fundamental in chemistry.
  • Understanding reaction mechanisms at a microscopic level is crucial for reaction control.

Purpose of the Study:

  • To investigate the effect of electron attachment on the cis-trans isomerization of maleonitrile.
  • To identify the microscopic mechanism enabling a barrierless reaction pathway.
  • To explore the potential of anionic activation for controlling chemical reactions.

Main Methods:

  • Theoretical calculations to model the potential energy surface of maleonitrile.
  • Analysis of electron-induced reaction pathways.
  • Identification of transition states and reaction mechanisms.

Main Results:

  • Attachment of a single electron facilitates a barrierless cis-trans isomerization pathway for maleonitrile.
  • Anionic activation enables control over isomer formation in both forward and reverse reaction directions.
  • The microscopic mechanism for the electron-induced barrierless isomerization was elucidated.

Conclusions:

  • Anionic activation by electron attachment is an effective strategy for lowering activation energy and controlling chemical reactions.
  • The demonstrated barrierless isomerization of maleonitrile highlights a novel approach to isomer synthesis.
  • The findings suggest potential generalization of this method to other chemical transformations.