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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.0K
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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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
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...
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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
9.9K
Basicity of Heterocyclic Aromatic Amines01:25

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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).
6.9K

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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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N,N'-Bis([1,1'-biphen-yl]-2-yl)-N-hy-droxy-methanimidamide.

Elizabeth Lamothe1, Arindam Saha1, Garry S Hanan1

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|October 8, 2025
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Summary

This study details the crystal structure of a novel compound (C25H20N2O). The molecule forms inversion dimers through hydrogen bonds, with C-H⋯π and π-π stacking interactions influencing crystal packing.

Keywords:
amidine N-oxidecrystal structureligand synthesis

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Understanding molecular interactions is crucial for materials science.
  • Crystal structure analysis reveals intermolecular forces.
  • The title compound's properties are influenced by its solid-state arrangement.

Purpose of the Study:

  • To determine the crystal structure of the title compound (C25H20N2O).
  • To identify the isomer and conformation of the molecule in the solid state.
  • To elucidate the intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed.
  • The crystal structure was solved and refined.
  • Analysis of hydrogen bonding and π-π stacking interactions was performed.

Main Results:

  • The compound crystallizes in the monoclinic space group C2/c.
  • It exists as the N-hydroxy-formamidine isomer in the E conformation.
  • Inversion dimers linked by O-H⋯N hydrogen bonds were observed.
  • C-H⋯π and π-π stacking interactions contribute to the crystal lattice.

Conclusions:

  • The crystal structure of C25H20N2O has been fully characterized.
  • Hydrogen bonding and π-π stacking are key factors in its solid-state organization.
  • This structural information provides insights into the compound's physical properties.