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Related Concept Videos

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
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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 molecule. These three...
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...

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Spin Saturation Transfer Difference NMR (SSTD NMR): A New Tool to Obtain Kinetic Parameters of Chemical Exchange Processes
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Published on: November 12, 2016

Spin capturing with nitrones: radical coupling reactions with concurrent introduction of mid-chain functionality.

Edgar H H Wong1, Cyrille Boyer2, Martina H Stenzel2

  • 1Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, Geb. 11.23, 76128 Karlsruhe, Germany. christopher.barner-kowollik@kit.edu tanja.junkers@monash.edu and Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of New South Wales, Sydney, NSW 2052, Australia.

Chemical Communications (Cambridge, England)
|March 4, 2010
PubMed
Summary

Nitrones efficiently mediate radical coupling reactions for polymer conjugation. This method creates macromolecules with functional alkoxyamine centers in their mid-chain locations.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Atom Transfer Radical Polymerization (ATRP) is a controlled polymerization technique.
  • Functional alkoxyamine centers are valuable for polymer modification and applications.

Purpose of the Study:

  • To demonstrate the efficacy of nitrones in mediating radical coupling reactions.
  • To conjugate polymers synthesized via ATRP using nitrone chemistry.
  • To introduce distinct functional alkoxyamine centers into polymer chains.

Main Methods:

  • Utilizing nitrones as mediators for radical coupling reactions.
  • Employing Atom Transfer Radical Polymerization (ATRP) for polymer synthesis.
  • Conjugating ATRP-made polymers through nitrone-mediated coupling.

Main Results:

  • Nitrones efficiently mediated the radical coupling of ATRP-synthesized polymers.
  • Macromolecules with precisely located alkoxyamine centers were successfully synthesized.
  • The functional alkoxyamine centers were confirmed to be in mid-chain positions.

Conclusions:

  • Nitrones provide an efficient pathway for polymer conjugation.
  • This methodology allows for the precise placement of functional groups within polymer chains.
  • The developed approach is valuable for creating advanced polymeric materials.