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Related Concept Videos

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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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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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A covalently bonded heteronuclear diatomic molecule can be modeled as two vibrating masses connected by a spring. The vibrational frequency of the bond can be expressed using an equation derived from Hooke's law, which describes how the force applied to stretch or compress a spring is proportional to the displacement of the spring. In this case, the atoms behave like masses, and the bond acts like a spring.
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A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
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Modulation of Prins Cyclization by Vibrational Strong Coupling.

Kenji Hirai1,2,3, Rie Takeda1,2, James A Hutchison4

  • 1Division of Photonics and Optical Science, Research Institute for Electronic Science (RIES), Hokkaido University, North 20 West 10, Kita ward, Sapporo, Hokkaido, Japan.

Angewandte Chemie (International Ed. in English)
|January 24, 2020
PubMed
Summary

Vibrational strong coupling (VSC) modifies chemical reactions. This study shows VSC decreases reaction rates for Prins cyclization in aldehydes and ketones, suggesting VSC is a viable tool for synthetic chemistry.

Keywords:
Rabi splittingcyclizationsinfrared spectroscopykineticsvibrational strong coupling

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Area of Science:

  • Chemistry
  • Physical Chemistry
  • Chemical Physics

Background:

  • Light-molecule strong coupling is a novel approach to control chemical reactions.
  • Vibrational strong coupling (VSC) has recently been shown to alter chemical reactivity.
  • Previous VSC studies focused on limited reactions like solvolysis and deprotection.

Purpose of the Study:

  • To investigate the impact of VSC on Prins cyclization reactions involving aldehydes and ketones.
  • To determine how VSC affects the kinetics and thermodynamics of this important synthetic transformation.
  • To expand the scope of reactions amenable to VSC modification.

Main Methods:

  • Subjecting a series of aldehydes and ketones to Prins cyclization under VSC conditions.
  • Measuring the second-order rate constants for the reactions.
  • Analyzing changes in activation energy, enthalpy, and entropy.

Main Results:

  • A decrease in the second-order rate constant was observed with VSC of reactant carbonyl stretching groups.
  • VSC led to an increase in activation energy.
  • Proportional changes in activation enthalpy and entropy indicated no significant alteration of the reaction pathway.

Conclusions:

  • VSC can effectively slow down Prins cyclization reactions.
  • The observed thermodynamic changes suggest VSC influences the reaction kinetics without changing the fundamental mechanism.
  • This work adds cycloaddition reactions to the list of VSC-modified reactions, supporting VSC as a synthetic tool.