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Spin–Spin Coupling Constant: Overview01:08

Spin–Spin Coupling Constant: Overview

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In bromoethane, the three methyl protons are coupled to the two methylene protons that are three bonds away. In accordance with the n+1 rule, the signal from the methyl protons is split into three peaks with 1:2:1 relative intensities. The methylene protons appear as a quartet, with the relative intensities of 1:3:3:1.
Qualitatively, any spin plus-half nucleus polarizes the spins of its electrons to the minus-half state. Consequently, the paired electron in the hydrogen–carbon bond must...
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NMR Spectroscopy: Spin–Spin Coupling01:08

NMR Spectroscopy: Spin–Spin Coupling

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The spin state of an NMR-active nucleus can have a slight effect on its immediate electronic environment. This effect propagates through the intervening bonds and affects the electronic environments of NMR-active nuclei up to three bonds away; occasionally, even farther. This phenomenon is called spin–spin coupling or J-coupling. Coupling interactions are mutual and result in small changes in the absorption frequencies of both nuclei involved. While nuclei of the same element are involved...
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Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

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

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

1.6K
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...
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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

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

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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.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...
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Atomic Nuclei: Nuclear Spin01:08

Atomic Nuclei: Nuclear Spin

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All atomic particles possess an intrinsic angular momentum, or 'spin'. Electrons, protons, and neutrons each have a spin value of ½, although protons and neutrons in nuclei may have higher half-integer spins owing to energetic factors.
Atomic nuclei have a net nuclear spin, , which can have an integer or half-integer value. In atomic nuclei, the spins of protons are paired against each other but not with neutrons, and vice versa. Consequently, an even number of protons does not contribute to...
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Persistent Organic High-Spin Trinitrenes.

Enrique Mendez-Vega1, Joel Mieres-Perez1, Sergei V Chapyshev2

  • 1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, 44780, Bochum, Germany.

Angewandte Chemie (International Ed. in English)
|July 3, 2019
PubMed
Summary
This summary is machine-generated.

Stable trinitrenes, molecules with six unpaired electrons, were synthesized and isolated. These compounds exhibit surprising unreactivity towards oxygen and hydrogen, persisting even in water ice at elevated temperatures.

Keywords:
IR spectroscopymatrix isolationnitrenesphotochemistryseptet

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Spectroscopy

Background:

  • Trinitrenes are high-spin organic molecules with potential applications in materials science.
  • Previous studies on similar high-spin molecules have shown varying degrees of reactivity.
  • Understanding the stability and reactivity of trinitrenes is crucial for their practical use.

Purpose of the Study:

  • To synthesize and characterize novel septet ground state trinitrenes.
  • To investigate the stability and reactivity of these trinitrenes in different matrices.
  • To explore the influence of matrix environment on trinitrene persistence.

Main Methods:

  • UV photolysis of corresponding triazides to generate trinitrenes.
  • Isolation of trinitrenes in inert (Ar, Ne, Xe) and reactive (H2, O2, H2O) matrices at cryogenic temperatures.
  • Characterization using IR and UV/Vis spectroscopy.

Main Results:

  • 1,3,5-trichloro-2,4,6-trinitrenobenzene and 1,3,5-tribromo-2,4,6-trinitrenobenzene were synthesized in high yields.
  • Trinitrenes demonstrated remarkable unreactivity towards molecular oxygen and hydrogen.
  • The compounds remained persistent in water ice up to 160 K.

Conclusions:

  • Septet ground state trinitrenes can be synthesized and isolated under cryogenic conditions.
  • These trinitrenes exhibit exceptional stability and low reactivity, even in the presence of reactive gases.
  • The findings suggest potential for developing novel materials based on these persistent high-spin molecules.