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Related Concept Videos

¹H NMR: Complex Splitting01:13

¹H NMR: Complex Splitting

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.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied first.
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: 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.
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...
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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 π orbitals.
Noncovalent Attractions in Biomolecules02:35

Noncovalent Attractions in Biomolecules

Noncovalent attractions are associations within and between molecules that influence the shape and structural stability of complexes. These interactions differ from covalent bonding in that they do not involve sharing of electrons.
Four types of noncovalent interactions are hydrogen bonds, van der Waals forces, ionic bonds, and hydrophobic interactions.
Hydrogen bonding results from the electrostatic attraction of a hydrogen atom covalently bonded to a strong-electronegative atom like oxygen,...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

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Related Experiment Video

Updated: Jul 10, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Complementary quadruple hydrogen bonding in supramolecular copolymers.

G B W L Ligthart1, Haruki Ohkawa, Rint P Sijbesma

  • 1Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.

Journal of the American Chemical Society
|January 20, 2005
PubMed
Summary

This study introduces a novel supramolecular copolymer utilizing quadruple hydrogen bonding. These advanced polymers maintain a high degree of polymerization across diverse compositions, outperforming existing systems.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Published on: February 15, 2016

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay
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Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

Published on: February 28, 2025

Area of Science:

  • Supramolecular Chemistry
  • Polymer Science
  • Organic Chemistry

Background:

  • Supramolecular polymers rely on non-covalent interactions for their structure and properties.
  • Previous systems often showed limited stability or composition tolerance.
  • Quadruple hydrogen bonding offers robust and directional molecular recognition.

Purpose of the Study:

  • To develop a supramolecular copolymer using a specific quadruple hydrogen bonding motif.
  • To investigate the impact of complementary hydrogen-bonding units on polymer properties.
  • To assess the stability and composition range of the resulting supramolecular copolymer.

Main Methods:

  • Synthesis of ureido-pyrimidinone and 2,7-diamido-1,8-naphthyridine monomers.
  • Polymerization via quadruple hydrogen bonding interactions.
  • Characterization of polymer properties, including degree of polymerization (DP) and composition tolerance.

Main Results:

  • Successful formation of a supramolecular copolymer through quadruple hydrogen bonding.
  • Demonstrated high degree of polymerization (DP) for the copolymer.
  • The copolymer maintained high DP across a wide range of monomer compositions.

Conclusions:

  • Quadruple hydrogen bonding provides a robust platform for supramolecular copolymer synthesis.
  • The developed system exhibits superior composition tolerance compared to prior complementary hydrogen-bonding polymers.
  • This work opens avenues for designing advanced materials with tunable properties.