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Radical Reactivity: Overview01:11

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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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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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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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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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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Computational Study on Radical-Mediated Thiol-Epoxy Reactions.

Belma Gjergjizi Nallbani1, Memet Vezir Kahraman1, Isa Degirmenci2

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Radical-mediated reactions between thiols and epoxides are slow for addition but fast for chain transfer. This explains curing system overlap, suggesting temperature and thiol choice can prevent it.

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Area of Science:

  • Polymer Chemistry
  • Computational Chemistry

Background:

  • Thiol-ene and thiol-epoxy systems are widely used in industrial applications.
  • Understanding the reaction mechanisms is crucial for optimizing curing processes and preventing system overlap.

Purpose of the Study:

  • To elucidate radical-mediated thiol-epoxy reactions using computational methods.
  • To analyze the overlap problem in dual curing systems (thiol-ene/thiol-epoxy).
  • To propose a reaction mechanism for radical-mediated thiol-epoxide reactions.

Main Methods:

  • Density Functional Theory (DFT) calculations.
  • Evaluation of nine epoxy model molecules.
  • Modeling reaction mechanisms at 1.0 atm and 298.15 K using M06-2X/6-31+G(d,p).

Main Results:

  • A thiol-ene analog mechanism was proposed for thiol-epoxide reactions.
  • Epoxide addition reactions are slow (rate constants <10⁻⁴ M⁻¹ s⁻¹).
  • Chain transfer reactions are fast (rate constants >10¹ M⁻¹ s⁻¹), leading to curing system overlap.
  • Key driving forces include thiyl radical stability, epoxy ring strain, and alkoxy radical instability.

Conclusions:

  • The fast chain transfer in thiol-epoxy reactions contributes to curing step overlap.
  • Control of reaction temperature and careful selection of thiols are recommended to manage curing overlap.
  • Computational insights provide a basis for optimizing dual curing systems.