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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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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.
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...
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Frost Circles for Different Conjugated Systems01:18

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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Noncovalent Attractions in Biomolecules02:35

Noncovalent Attractions in Biomolecules

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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.
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Noncovalent Attractions in Biomolecules

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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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  3. Exploring Non-covalent Interactions In Binary Aromatic Complexes.
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  3. Exploring Non-covalent Interactions In Binary Aromatic Complexes.

Related Experiment Video

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Exploring non-covalent interactions in binary aromatic complexes.

Joseph C Bear1, Jeremy K Cockcroft2, Alexander Rosu-Finsen2

  • 1School of Life Sciences, Pharmacy and Chemistry, Kingston University Penrhyn Road Kingston upon Thames KT1 2EE UK.

Crystengcomm
|December 12, 2025

View abstract on PubMed

Summary
This summary is machine-generated.

Systematic halogen substitution in fluorinated aromatics influences co-crystal structures with p-xylene. Heavier halogens promote halogen bonding, enabling tunable solid-state architectures and advancing crystal design.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

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Area of Science:

  • Solid-state chemistry
  • Supramolecular chemistry
  • Materials science

Background:

  • Predicting crystal structures with weak interactions is challenging.
  • Halogen bonding and π-stacking are key non-covalent interactions in crystal engineering.
  • Fluorinated aromatics offer tunable electronic and steric properties.

Purpose of the Study:

  • Investigate the effect of halogen substitution on co-crystal formation with p-xylene.
  • Characterize the structural evolution from π-stacked to halogen-bonded systems.
  • Explore the phase behavior and intermolecular interactions in these co-crystals.

Main Methods:

  • Differential scanning calorimetry (DSC) for thermal analysis.
  • Variable-temperature powder X-ray diffraction (VT-PXRD) for phase behavior.
  • Single-crystal X-ray diffraction (SXD) for detailed structural determination.

    • Main Results:

    • Observed a transition from columnar π-stacked adducts (Cl) to halogen-bonded structures (Br, I).
    • Columnar 1:1 adducts showed complex phase behavior due to dipole and steric effects.
    • Discrete halogen-π interactions (η², η⁶) were identified with heavier halogens.
    • A 1:2 co-crystal with antiferroelectric ordering was formed via halogen bonding.

    Conclusions:

    • Halogen substitution effectively tunes solid-state architectures and non-covalent interactions.
    • Provides insights into weak intermolecular forces for predictive co-crystal design.
    • Demonstrates the utility of halogen bonding in creating functional crystalline materials.