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Related Concept Videos

Radical Formation: Abstraction00:47

Radical Formation: Abstraction

3.9K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
3.9K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.0K
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.
4.0K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.0K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.0K
Hydrogen Bonds01:04

Hydrogen Bonds

11.4K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
11.4K
Hydrogen Bonds00:26

Hydrogen Bonds

128.0K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
128.0K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

4.5K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
4.5K

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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
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Insight into Hydrogen Abstractions by Nitrate Radical: Structural, Solvent Effects, and Evidence for a Polar

Mark Paradzinsky1, Diego Troya1, James M Tanko1

  • 1Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, United States.

The Journal of Physical Chemistry. A
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Nitrate radical reactions with ethers, alcohols, and alkanes show structure-reactivity trends explained by hydrogen count, C-H bond strength, and ionization potential. Polar transition states influence reaction rates in solvents.

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Quantification of Hydrogen Concentrations in Surface and Interface Layers and Bulk Materials through Depth Profiling with Nuclear Reaction Analysis
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Quantification of Hydrogen Concentrations in Surface and Interface Layers and Bulk Materials through Depth Profiling with Nuclear Reaction Analysis
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Area of Science:

  • Atmospheric Chemistry
  • Chemical Kinetics
  • Physical Organic Chemistry

Background:

  • Nitrate radical (NO3) is a key oxidant in the troposphere, influencing atmospheric composition.
  • Understanding the reactivity of NO3 with various organic compounds is crucial for atmospheric modeling.
  • Ethers represent an under-studied class of substrates concerning their reactions with NO3.

Purpose of the Study:

  • To investigate the role of polarized transition states and solvent effects in nitrate radical reactions.
  • To determine absolute rate constants for hydrogen abstraction from alcohols, ethers, and alkanes by NO3.
  • To explore the atmospheric implications of these reactions.

Main Methods:

  • Measurement of absolute rate constants for hydrogen abstraction by NO3 in acetonitrile, water, and solvent mixtures.
  • Application of a modified Evans-Polanyi relationship to analyze structure/reactivity trends.
  • Correlation of reactivity with substrate properties: number of abstractable hydrogens, C-H bond strength, and ionization potential (IP).

Main Results:

  • Observed structure/reactivity trends are consistent across alcohols, ethers, and alkanes.
  • Hydrogen abstractions by NO3 exhibit low selectivity and an early transition state (α ≈ 0.3).
  • Rate constants increase with decreasing IP, indicating a polar transition state with <10% charge transfer.

Conclusions:

  • The Evans-Polanyi relationship effectively reconciles reactivity trends based on substrate properties.
  • Polar transition states are characteristic of NO3 hydrogen abstraction reactions in both solution and gas phase.
  • Solvent polarity significantly impacts rate constants, with increases in polar solvents consistent with Kirkwood theory.