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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

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Related Experiment Video

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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5-Amino-1-naphthol.

Agnieszka Czapik1, Arkadiusz Nitka, Maria Gdaniec

  • 1Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study reveals that molecules of C(10)H(9)NO form a 2D polymer through hydrogen bonds. These molecules also exhibit pi-pi stacking interactions, creating slipped stacks within the crystal structure.

Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Hydrogen bonding plays a crucial role in the self-assembly of molecules.
  • Understanding intermolecular interactions is key to designing novel materials.
  • The crystal structure of organic compounds dictates their physical and chemical properties.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title compound, C(10)H(9)NO.
  • To investigate the role of amino and hydroxyl groups in hydrogen bonding and molecular assembly.
  • To analyze the presence and significance of pi-pi stacking interactions in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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  • Analysis of hydrogen bonding networks (N-H···O) to understand molecular connectivity.
  • Investigation of pi-pi stacking interactions between aromatic rings.
  • Main Results:

    • The compound C(10)H(9)NO forms a two-dimensional polymeric structure driven by intermolecular hydrogen bonds (N-H···O).
    • Molecules are arranged in slipped stacks facilitated by pi-pi stacking interactions with an inter-planar distance of 3.450(4) Å.
    • The amino nitrogen atom exhibits sp(3) hybridization, with its hydrogen atoms positioned on the same side of the aromatic ring.

    Conclusions:

    • The study successfully characterized the supramolecular architecture of C(10)H(9)NO, highlighting the interplay of hydrogen bonding and pi-pi stacking.
    • The observed 2D polymeric structure provides insights into crystal engineering strategies for organic molecules.
    • The findings contribute to the understanding of structure-property relationships in crystalline organic materials.