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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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.
Due to the absence of continuous overlap of p...

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Related Experiment Video

Updated: May 21, 2026

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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4-Cyano-pyridinium chloride.

Wen-Ni Zheng1

  • 1College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|June 22, 2012
PubMed
Summary

The crystal structure of pyridinium chloride reveals interactions between the pyridinium cation and chloride anion. These interactions are primarily driven by N-H⋯Cl hydrogen bonds, with additional weak C-H⋯Cl forces also observed.

Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding intermolecular forces is crucial in crystal engineering.
  • Pyridinium salts are common organic compounds with diverse applications.
  • The specific interactions within pyridinium chloride have been investigated to understand its structural properties.

Purpose of the Study:

  • To determine the crystal structure of pyridinium chloride.
  • To identify and characterize the intermolecular interactions present in the crystal lattice.
  • To elucidate the role of hydrogen bonding and other weak interactions in stabilizing the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to obtain the three-dimensional crystal structure.

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  • Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors.
  • Intermolecular interactions were further analyzed using geometric criteria.
  • Main Results:

    • The crystal structure of pyridinium chloride (C(6)H(5)N(2)(+)·Cl(-)) was successfully determined.
    • A significant N-H⋯Cl hydrogen bond was identified, linking the pyridinium cations and chloride anions.
    • Weak C-H⋯Cl interactions were also observed, contributing to the overall crystal packing.

    Conclusions:

    • The crystal structure is stabilized by a combination of strong N-H⋯Cl hydrogen bonds and weaker C-H⋯Cl interactions.
    • These findings provide insights into the supramolecular assembly of pyridinium salts.
    • The detailed understanding of these interactions can inform the design of new materials with tailored properties.