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Related Concept Videos

Bond Dissociation Energy and Activation Energy02:13

Bond Dissociation Energy and Activation Energy

Bond energy is the energy required to break a bond homolytically. These values are usually expressed in units of kcal/mol or kJ/mol and are referred to as bond dissociation energies when given for specific bonds or average bond energies when indicated for a given type of bond over many compounds. Firstly, the bond dissociation energy for a single bond is weaker than that of a double bond, which in turn is weaker than that of a triple bond. Secondly, hydrogen forms relatively strong bonds with...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Understanding and exploiting C-H bond activation.

Jay A Labinger1, John E Bercaw

  • 1Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, Pasadena, California 91125, USA. jal@its.caltech.edu

Nature
|May 31, 2002
PubMed
Summary

Scientists are advancing the selective transformation of carbon-hydrogen (C-H) bonds using transition metals. This research promises more efficient chemical synthesis and cleaner utilization of abundant alkane resources.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Carbon-hydrogen (C-H) bonds are abundant but inert, presenting a challenge for chemical synthesis.
  • Transition-metal catalysis has emerged as a powerful tool for C-H bond activation.
  • Significant progress has been made in understanding C-H activation mechanisms over the past two decades.

Purpose of the Study:

  • To review the advancements in transition-metal-catalyzed C-H bond activation.
  • To discuss the potential of these methods for practical applications in chemical synthesis and alkane conversion.
  • To highlight the ongoing development of catalytic systems for efficient and clean alkane resource utilization.

Main Methods:

  • Review of literature on transition-metal-catalyzed C-H bond activation.
  • Analysis of reaction mechanisms, selectivity, and conditions.
  • Evaluation of current and potential applications in fine chemical synthesis and feedstock replacement.

Main Results:

  • Numerous examples of selective C-H bond activation at transition-metal centers under mild conditions have been reported.
  • A deeper understanding of the mechanisms, advantages, and limitations of these organometallic reactions has been achieved.
  • Promising new catalytic systems demonstrate the feasibility of practical C-H activation strategies.

Conclusions:

  • Organometallic chemistry offers significant potential for efficient and selective C-H bond activation.
  • Further development of catalytic systems is crucial for realizing practical applications in alkane conversion.
  • These advancements pave the way for cleaner and more efficient utilization of Earth's alkane resources.