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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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.

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Updated: Jun 1, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Published on: June 20, 2014

1-Methyl-4,5-dinitro-1H-imidazole.

Yong-Xiang Li1, Xiao-Jun Wang, Jian-Long Wang

  • 1School of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China.

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

The crystal structure of a novel imidazole derivative reveals twisted nitro groups and intermolecular hydrogen bonding. This molecular arrangement influences its solid-state properties and potential applications.

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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

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Imidazole derivatives are important in medicinal chemistry and materials science.
  • Understanding the solid-state structure of novel compounds is crucial for predicting their properties.

Purpose of the Study:

  • To elucidate the crystal structure of a novel C(4)H(4)N(4)O(4) compound.
  • To analyze the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
  • Identification of intermolecular interactions, specifically C-H⋯O hydrogen bonds, was performed.

Main Results:

  • The crystal structure of C(4)H(4)N(4)O(4) was successfully determined.
  • The two nitro groups exhibit significant twisting relative to the imidazole ring, with dihedral angles of 24.2° and 33.4°.
  • Non-classical intermolecular C-H⋯O hydrogen bonds link the molecules in the crystal lattice.

Conclusions:

  • The non-planar conformation of the nitro groups is a key structural feature.
  • Intermolecular hydrogen bonding plays a significant role in stabilizing the crystal packing.
  • The findings provide a foundation for further studies on the properties and applications of this imidazole derivative.