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Related Concept Videos

Structure of Alkanes02:23

Structure of Alkanes

32.7K
The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes. 
Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms....
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Nomenclature of Alkanes02:22

Nomenclature of Alkanes

26.2K
In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...
26.2K
Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

Mass Spectrometry: Long-Chain Alkane Fragmentation

2.4K
The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
2.4K
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

21.9K
Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the...
21.9K
Physical Properties of Alkanes02:33

Physical Properties of Alkanes

14.1K
Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...
14.1K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

9.8K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
9.8K

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Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation
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Room Temperature Acceptorless Alkane Dehydrogenation from Molecular σ-Alkane Complexes.

Alasdair I McKay1, Alexander J Bukvic1, Bengt E Tegner2

  • 1Chemistry Research Laboratories, University of Oxford , Oxford OX1 3TA , United Kingdom.

Journal of the American Chemical Society
|June 28, 2019
PubMed
Summary

This study uses solid-state molecular organometallic chemistry to activate C-H bonds in alkanes at room temperature, enabling non-oxidative dehydrogenation. This breakthrough offers a new pathway for catalytic alkane functionalization.

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Visualizing Single Molecular Complexes In Vivo Using Advanced Fluorescence Microscopy
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Visualizing Single Molecular Complexes In Vivo Using Advanced Fluorescence Microscopy

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Solid-State Chemistry

Background:

  • Non-oxidative catalytic dehydrogenation of light alkanes via C-H activation is challenging due to high endothermicity and unfavorable thermodynamics.
  • Alkanes are poor ligands, making their binding to metal centers prior to C-H activation difficult.
  • High temperatures or sacrificial hydrogen acceptors are typically required to overcome thermodynamic barriers.

Purpose of the Study:

  • To demonstrate a novel method for activating alkane C-H bonds under mild conditions using solid-state molecular organometallic chemistry (SMOM-chem).
  • To prepare and characterize well-defined alkane sigma-complexes.
  • To investigate the dehydrogenation mechanism and kinetics of these complexes.

Main Methods:

  • Synthesis of rhodium-alkane sigma-complexes ([Rh(Cy2PCH2CH2PCy2)(alkane)][BArF4]) via solid/gas single-crystal to single-crystal transformation of precursor alkene complexes.
  • Solid-gas H/D exchange experiments with D2 to probe C-H bond reactivity.
  • Variable temperature solid-state nuclear magnetic resonance (NMR) spectroscopy and periodic density functional theory (DFT) calculations to study fluxional processes and reaction mechanisms.
  • Kinetic studies, including kinetic isotope effects (KIEs), and modeling using classical chemical kinetics or Johnson-Mehl-Avrami-Kolmogorov (JMAK) models.

Main Results:

  • Well-defined isobutane and cyclohexane sigma-complexes were successfully prepared and characterized.
  • Spontaneous, acceptorless dehydrogenation of alkane sigma-complexes to alkene complexes occurred at 298 K under vacuum or Ar-flow.
  • Kinetic isotope effects (kH/kD = 3.6(5) and 10.8(6)) for cyclohexane dehydrogenation indicated C-H activation as the rate-determining step.
  • Periodic DFT calculations supported experimental findings, predicting activation barriers and elucidating the mechanism involving C-H bond elongation and beta-H transfer.

Conclusions:

  • Solid-state molecular organometallic chemistry (SMOM-chem) enables the preparation of alkane sigma-complexes and their subsequent dehydrogenation under mild conditions.
  • The study provides direct experimental evidence for C-H activation in alkane dehydrogenation, supported by kinetic and computational data.
  • This approach offers a promising new avenue for catalytic functionalization of alkanes, overcoming thermodynamic limitations.