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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).
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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Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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2-Phenyl-1H-imidazole.

Maryam Mehdizadeh Barforoush1, Soheila Naderi, Ali Reza Ghanbarpour

  • 1Department of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran.

Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
PubMed
Summary

This study details the crystal structure of a phenylimidazole compound, C(9)H(8)N(2). The imidazole ring exhibits disorder, and molecules are linked by hydrogen bonds in the crystal lattice.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding molecular arrangements in solid-state is crucial for material properties.
  • Phenylimidazole derivatives are common scaffolds in medicinal chemistry and materials science.
  • Detailed structural analysis provides insights into intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(9)H(8)N(2).
  • To investigate the molecular symmetry and disorder in the crystal lattice.
  • To characterize the intermolecular interactions, specifically hydrogen bonding.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Crystallographic data were collected and refined to obtain precise atomic coordinates.
  • Analysis of the crystal packing and hydrogen bonding network was performed.

Main Results:

  • The crystal structure reveals a phenylimidazole compound with the chemical formula C(9)H(8)N(2).
  • A crystallographic mirror plane bisects the molecule, leading to disorder of the imidazole ring over two equally occupied sites.
  • The asymmetric unit contains one half-molecule, indicating molecular symmetry.
  • Intermolecular N-H⋯N hydrogen bonds link adjacent molecules, forming a crystal network.

Conclusions:

  • The crystal structure of C(9)H(8)N(2) has been successfully determined.
  • The observed disorder and hydrogen bonding provide insights into the solid-state behavior of this phenylimidazole derivative.
  • This structural information can be valuable for further research in related chemical and material science applications.