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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.3K
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.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.3K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

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

1.3K
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...
1.3K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.3K
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,...
1.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

11.7K
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.
11.7K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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

1.4K
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...
1.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.2K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.2K

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Attaching Biological Probes to Silica Optical Biosensors Using Silane Coupling Agents
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Long-range coupling in cyclic silanes.

John T Ferguson1, Qifeng Jiang, Eric A Marro

  • 1Deprtment of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. klausen@jhu.edu.

Dalton Transactions (Cambridge, England : 2003)
|October 20, 2020
PubMed
Summary
This summary is machine-generated.

We synthesized a novel cyclosilane with distinct stereoisomers. NMR spectroscopy confirmed four-bond proton-proton coupling, revealing configuration-dependent molecular interactions.

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Area of Science:

  • Organosilicon chemistry
  • Stereochemistry
  • Spectroscopy

Background:

  • Cyclosilanes are versatile silicon-based compounds.
  • Stereoisomerism in cyclosilanes influences their properties.
  • Long-range proton-proton coupling is crucial for structural elucidation.

Purpose of the Study:

  • To synthesize and characterize a mixed methyl- and hydro-substituted cyclosilane.
  • To investigate the stereoisomerism (cis/trans) and symmetry of the cyclosilane.
  • To probe configuration- and conformation-dependent long-range proton-proton coupling.

Main Methods:

  • Synthesis of cyclosilane 1.
  • Extensive Nuclear Magnetic Resonance (NMR) spectroscopy.
  • One-dimensional (1D) 1H NMR, 29Si DEPT, and INEPT+.
  • Two-dimensional (2D) 1H-29Si HSQC, HMBC, and 1H-1H COSY.

Main Results:

  • Successful synthesis of mixed methyl- and hydro-substituted cyclosilane (1).
  • Identification of cis and trans diastereomers with distinct symmetry elements (Cs and C2, respectively).
  • Confirmation of four-bond 1H-1H coupling through detailed NMR analysis.

Conclusions:

  • The synthesized cyclosilane serves as a model system for studying stereochemical effects on coupling.
  • NMR spectroscopy effectively characterized the stereoisomers and confirmed long-range coupling.
  • This study advances the understanding of structure-property relationships in organosilicon compounds.