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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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Radical Reactivity: Nucleophilic Radicals01:16

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Using the general-purpose reactivity indicator: challenging examples.

James S M Anderson1,2, Junia Melin3, Paul W Ayers4

  • 1Computational Materials Science Research Team, AICS, RIKEN, Kobe, Hyogo, 650-0047, Japan. james.anderson@riken.jp.

Journal of Molecular Modeling
|February 18, 2016
PubMed
Summary
This summary is machine-generated.

We explored nucleophilic attack regioselectivity using a general-purpose reactivity indicator (GPRI). The GPRI accurately identifies kinetically favored products but requires careful interpretation to avoid unreactive sites.

Keywords:
Conceptual density functional theoryElectrostatic potentialFukui functionGeneral purpose reactivity indicatorReactivity transition table

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Understanding regioselectivity in nucleophilic aromatic substitution is crucial for synthetic chemistry.
  • Existing computational tools may not fully account for steric and electronic factors influencing reactivity.

Purpose of the Study:

  • To evaluate the utility of a general-purpose reactivity indicator (GPRI) for predicting nucleophilic attack sites.
  • To assess the accuracy and limitations of the GPRI in complex organic molecules.

Main Methods:

  • Application of the GPRI to substituted benzenesulfonates, quinolines, and pyridines.
  • Analysis of GPRI predictions against known reaction outcomes and steric considerations.

Main Results:

  • The GPRI shows high accuracy when nucleophiles approximate point charges.
  • The GPRI can identify kinetically favored reaction sites and distinguish between hard/soft reagent interactions.
  • The GPRI may incorrectly identify sterically hindered or unreactive 'dead end' sites.

Conclusions:

  • The GPRI is a valuable interpretative tool for understanding electrophilic reactivity and regioselectivity.
  • Careful consideration of steric hindrance and inherent reactivity is necessary when using the GPRI.
  • The GPRI complements, but does not replace, traditional computational methods like Density Functional Theory (DFT).