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Related Concept Videos

Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.8K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
4.8K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.6K
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.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.3K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Updated: Aug 23, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Interheteromolecular Hyperconjugation Boosts (De)hydrogenation for Reversible H2 Storage.

Wenjie Xue1, Hongxia Liu2, Binbin Zhao3

  • 1Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, Hubei, 430074, China.

Chemsuschem
|November 2, 2022
PubMed
Summary

Interheteromolecular hyperconjugation in N-heterocycles like N-ethylcarbazole (NEC) and N-propylcarbazole (NPC) enhances catalytic hydrogenation reactivity. This phenomenon enables efficient hydrogenation at low temperatures for reversible hydrogen storage applications.

Keywords:
eutectic mixtureshydrogen carriershydrogen storagehydrogenationhyperconjugation

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Physical Chemistry

Background:

  • Interheteromolecular hyperconjugation influences molecular properties in organic systems.
  • Its impact on heterogeneous catalytic (de)hydrogenation remains largely unexplored.

Purpose of the Study:

  • To investigate the correlation between interheteromolecular hyperconjugation and catalytic (de)hydrogenation reactivity.
  • To explore the application of this phenomenon in heterogeneous thermocatalysis for hydrogen storage.

Main Methods:

  • Density functional theory (DFT) calculations.
  • Variable-temperature 1H nuclear magnetic resonance (NMR) spectroscopy.
  • Heterogeneous catalytic experiments and isotope labeling studies.

Main Results:

  • Interheteromolecular hyperconjugation in N-ethylcarbazole (NEC) and N-propylcarbazole (NPC) weakens aromatic electron density, facilitating reaction with hydrogen.
  • Efficient hydrogenation was achieved at a low temperature of 80°C.
  • The observed hyperconjugation effect is general across various N-heterocycles and effective for deuteration.

Conclusions:

  • Interheteromolecular hyperconjugation significantly enhances catalytic (de)hydrogenation.
  • This study demonstrates a novel approach for reversible hydrogen storage using N-heterocycles.
  • The findings expand the application scope of hyperconjugation in heterogeneous thermocatalysis.