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Related Concept Videos

Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

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The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
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¹³C NMR: ¹H–¹³C Decoupling01:04

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The probability of having two carbon-13 atoms next to each other is negligible because of the low natural abundance of carbon-13. Consequently, peak splitting due to carbon-carbon spin-spin coupling is not observed in spectra. However, protons up to three sigma bonds away split the carbon signal according to the n+1 rule, resulting in complicated spectra.
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Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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

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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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Hyperpolarized 13C Metabolic Magnetic Resonance Spectroscopy and Imaging
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Dynamic Nuclear Polarization of β-Cyclodextrin Macromolecules.

Filippo Caracciolo1, Pietro Carretta1, Marta Filibian1

  • 1Department of Physics, University of Pavia , Via Bassi 6, 27100 Pavia, Italy.

The Journal of Physical Chemistry. B
|March 7, 2017
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Summary

Dynamic nuclear polarization in TEMPO-doped cyclodextrins enhances nuclear spin polarization up to 10%. This study reveals relaxation mechanisms driven by glassy dynamics and molecular motions, relevant for in vivo applications.

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Area of Science:

  • Solid-state Nuclear Magnetic Resonance (NMR) Spectroscopy
  • Materials Science
  • Chemical Physics

Background:

  • Dynamic nuclear polarization (DNP) significantly enhances NMR signal sensitivity.
  • Amorphous cyclodextrin complexes offer a matrix for radical doping.
  • Understanding electron-nucleus interactions is crucial for DNP efficiency.

Purpose of the Study:

  • To investigate 1H dynamic nuclear polarization (DNP) and spin-lattice relaxation rates in amorphous beta-cyclodextrin/TEMPO radical complexes.
  • To elucidate the mechanisms governing nuclear polarization buildup and relaxation.
  • To assess the relevance of these systems for in vivo NMR applications.

Main Methods:

  • Proton (1H) dynamic nuclear polarization (DNP) experiments.
  • Measurement of nuclear spin-lattice relaxation rates (1/T1n).
  • Variable temperature studies and analysis of radical concentration effects.

Main Results:

  • Achieved nuclear polarization enhancements up to 10% under optimal conditions.
  • Observed DNP buildup rates and relaxation behavior consistent with a thermal mixing regime.
  • Demonstrated that temperature dependence and radical concentration effects on 1/T1n are governed by glassy dynamics and molecular motions.

Conclusions:

  • The study elucidates the relaxation mechanisms in amorphous cyclodextrin/TEMPO systems, driven by electron-nucleus coupling modulated by glassy dynamics.
  • Findings suggest these systems have potential for in vivo applications due to relaxation behavior at biologically relevant dilution levels.
  • The observed thermal mixing regime provides insights into optimizing DNP enhancement in similar solid-state systems.