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Related Concept Videos

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).
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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

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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

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1-Methyl-5-nitro-1H-imidazole.

Ying Diao1, Wen-Yan Wang, Zhi-Hua Wei

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

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary
This summary is machine-generated.

The crystal structure of a nitroimidazole compound reveals a slight twist between the nitro group and the imidazole ring. This arrangement is stabilized by weak intermolecular hydrogen bonds involving carbon, oxygen, and nitrogen atoms.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Imidazole derivatives are important in medicinal chemistry.
  • Understanding molecular conformation is crucial for predicting chemical properties.
  • Nitro groups can significantly influence electronic and structural characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of a specific nitroimidazole compound.
  • To quantify the dihedral angle between the nitro group and the imidazole ring.
  • To identify and characterize intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • The crystal structure was solved and refined.
  • Intermolecular hydrogen bonding was analyzed.

Main Results:

  • The compound's chemical formula is C(4)H(5)N(3)O(2).
  • A dihedral angle of 5.60(2)° was measured between the nitro group and the imidazole ring.
  • Weak intermolecular C-H⋯O and C-H⋯N hydrogen bonds were identified.

Conclusions:

  • The crystal packing is influenced by weak hydrogen bonding.
  • The observed conformation provides insights into the solid-state behavior of nitroimidazoles.
  • This structural data can inform the design of related compounds.