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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
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.
Removing one hydrogen from the intervening CH2 group...
3.5K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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...
3.5K
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.7K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
3.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
1.9K

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Related Experiment Video

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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3-Hy-droxy-anilinium p-toluene-sulfonate.

Impichira Pykkat Bincy1, Rengasamy Gopalakrishnan

  • 1Department of Physics, Anna University, Chennai 600 025, India.

Acta Crystallographica. Section E, Structure Reports Online
|October 11, 2013
PubMed
Summary

This study details the crystal structure of a novel salt, C6H8NO(+)·C7H7O3S(-). Extensive hydrogen bonding between cations and anions forms a robust three-dimensional network.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding the crystal packing and intermolecular interactions of organic salts is crucial for designing new materials.
  • Hydrogen bonding plays a significant role in directing the self-assembly of molecular structures.
  • The specific salt, C6H8NO(+)·C7H7O3S(-), has not been previously characterized in terms of its solid-state structure.

Purpose of the Study:

  • To determine the crystal structure of the title salt, C6H8NO(+)·C7H7O3S(-).
  • To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
  • To characterize the resulting network motifs and their contribution to the overall three-dimensional structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.

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  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of hydrogen bonding and network topology was performed using crystallographic tools.

    • Main Results:

    • The asymmetric unit contains two cations (C6H8NO(+)) and two anions (C7H7O3S(-)).
    • Extensive N-H⋯O and O-H⋯O hydrogen bonds were identified between cations and anions.
    • These interactions lead to the formation of specific ring motifs, namely R 4 (4)(18) and R 2 (1)(4).
    • A robust three-dimensional network structure is formed through these hydrogen-bonding interactions.

    Conclusions:

    • The crystal structure of C6H8NO(+)·C7H7O3S(-) has been successfully elucidated.
    • Hydrogen bonding is the primary driving force for the self-assembly and stabilization of the crystal structure.
    • The identified network motifs provide insights into the supramolecular architecture and potential properties of this organic salt.