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Free-energy diagrams, or reaction coordinate diagrams, are graphs showing the energy changes that occur during a chemical reaction. The reaction coordinate represented on the horizontal axis shows how far the reaction has progressed structurally. Positions along the x-axis close to the reactants have structures resembling the reactants, while positions close to the products resemble the products.  Peaks on the energy diagram represent stable structures with measurable lifetimes, while...
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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Adventures in Reactive Intermediate Chemistry: A Perspective and Retrospective.

Robert A Moss1

  • 1Department of Chemistry and Chemical Biology, Rutgers University, The State University of New Jersey , New Brunswick, New Jersey 08903, United States.

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Summary

This review explores the physical organic chemistry of reactive intermediates like carbenes and carbocations. It covers their formation, reactivity, and diverse chemical behaviors.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • Reactive intermediates, such as carbenes and carbocations, are crucial in understanding chemical reactions.
  • Their unique electronic structures and reactivity patterns present significant challenges and opportunities in synthetic chemistry.

Purpose of the Study:

  • To provide a comprehensive review of research on the physical organic chemistry of carbenes and carbocations.
  • To highlight key aspects including carbenoids, carbenic philicity, reaction rates, and carbocation generation.

Main Methods:

  • Literature review of experimental and theoretical studies on carbenes and carbocations.
  • Analysis of reaction mechanisms, kinetics, and thermodynamic properties.
  • Discussion of various synthetic routes and their associated intermediates.

Main Results:

  • Detailed examination of carbenoid chemistry and the concept of carbenic philicity.
  • Quantification of absolute rates for carbene/alkene addition reactions.
  • Exploration of carbocation formation pathways from diazotates and alkoxychlorocarbenes.

Conclusions:

  • Carbenes and carbocations exhibit diverse and complex reactivity, underscoring their protean nature.
  • Understanding these intermediates is vital for advancing physical organic chemistry and synthetic methodologies.
  • The research emphasizes the dynamic and multifaceted behavior of these key reactive species.