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Related Concept Videos

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...

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Related Experiment Video

Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

2,4-Dinitro-1-naphthol.

Abdul Rauf Raza, Aeysha Sultan, M Nawaz Tahir

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(10)H(6)N(2)O(5) compound, revealing near co-planar fused rings and specific nitro group orientations. Molecular interactions, including hydrogen bonds and pi-pi stacking, stabilize the crystal lattice.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the solid-state structure of organic compounds is crucial for predicting their properties.
    • Nitro-substituted aromatic systems exhibit diverse chemical and physical behaviors.
    • Intermolecular forces significantly influence crystal packing and material characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(10)H(6)N(2)O(5).
    • To analyze the molecular geometry, including ring planarity and nitro group orientations.
    • To investigate the intermolecular interactions, such as hydrogen bonding and pi-pi stacking, that stabilize the crystal structure.

    Main Methods:

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

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  • Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
  • Identification and analysis of intra- and intermolecular hydrogen bonds and pi-pi interactions.

    • Main Results:

    • The fused ring system in C(10)H(6)N(2)O(5) is nearly co-planar (r.m.s. deviation of 0.0163 Å).
    • Nitro groups exhibit distinct dihedral angles (2.62° and 44.69°) relative to the fused ring plane.
    • Intramolecular hydrogen bonds form S(6) ring motifs, and intermolecular hydrogen bonds link molecules into chains along the [101] direction.
    • Significant pi-pi interactions with centroid-centroid distances ranging from 3.6296 to 3.8104 Å were observed.

    Conclusions:

    • The crystal structure of C(10)H(6)N(2)O(5) is characterized by a nearly planar fused ring system and specific nitro group orientations.
    • Intramolecular and intermolecular hydrogen bonding play a key role in the molecular and crystal structure.
    • Pi-pi interactions are likely important contributors to the overall stability of the crystal packing.