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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Inorganic Nitrogen Assimilation01:22

Inorganic Nitrogen Assimilation

Nitrogen is an essential element in biological systems, forming a crucial component of proteins, nucleic acids, and other cellular constituents. Many bacteria and archaea acquire nitrogen in the form of nitrate (NO₃⁻) or ammonia (NH₃), which are then assimilated into biomolecules through specific enzymatic pathways.Assimilatory Nitrate ReductionWhen nitrate enters the cell, it undergoes a two-step reduction process known as assimilatory nitrate reduction. Initially, the enzyme nitrate reductase...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Indole-3-thio-uronium nitrate.

Martin Lutz, Anthony L Spek, Erwin P L van der Geer

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The crystal structure of a novel indole-thiouronium nitrate compound reveals a near-perpendicular arrangement between the indole and thiouronium groups. These molecules form 2D networks linked by pi-stacking interactions, showcasing unique supramolecular assembly in organic nitrates.

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    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Indole derivatives are prevalent in biologically active molecules and materials science.
    • Thiouronium salts are versatile intermediates in organic synthesis and coordination chemistry.
    • Understanding crystal packing and intermolecular interactions is crucial for designing novel materials.

    Purpose of the Study:

    • To elucidate the crystal structure and supramolecular assembly of a novel indole-thiouronium nitrate compound.
    • To investigate the spatial arrangement and intermolecular interactions within the crystal lattice.
    • To provide insights into the role of hydrogen bonding and pi-stacking in the self-assembly of organic nitrate salts.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was performed to determine the three-dimensional molecular structure.
    • Analysis of hydrogen bonding and non-covalent interactions (e.g., pi-stacking) was conducted.
    • Geometric parameters, including dihedral angles and inter-planar distances, were precisely measured.

    Main Results:

    • The crystal structure of C(9)H(10)N(3)S(+)·NO(3)(-) was successfully determined.
    • A near-perpendicular orientation (dihedral angle of 88.62°) was observed between the indole ring system and the thiouronium group.
    • Two-dimensional hydrogen-bonded networks were formed, further interconnected by pi-stacking interactions between indole groups (average inter-planar distance of 3.449 Å).

    Conclusions:

    • The study reveals a unique supramolecular architecture driven by hydrogen bonding and pi-stacking interactions.
    • The observed structural features provide a foundation for understanding the solid-state properties of indole-thiouronium nitrate compounds.
    • This research contributes to the field of crystal engineering and the design of functional organic materials.