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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).
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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.
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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Related Experiment Video

Updated: Jun 1, 2026

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

N-Benzyl-pyridin-2-amine.

Gai Gai Wang1, Hong Zhao

  • 1School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

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

The crystal structure of C(12)H(12)N(2) reveals a significant dihedral angle between its benzene and pyridine rings. Molecules form dimers through intermolecular hydrogen bonds, a common structural motif in organic compounds.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Intermolecular interactions, such as hydrogen bonding, play a key role in the self-assembly of molecules into larger structures.
  • The study of crystal structures provides fundamental insights into molecular geometry and intermolecular forces.

Purpose of the Study:

  • To determine the precise crystal structure of the title compound, C(12)H(12)N(2).
  • To analyze the dihedral angle between the aromatic rings within the molecule.
  • To investigate the intermolecular interactions responsible for the compound's solid-state organization.

Main Methods:

  • Single-crystal X-ray diffraction was employed to obtain the detailed molecular structure.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Published on: February 6, 2020

  • The crystal packing was analyzed to identify and characterize intermolecular interactions.
  • Geometric parameters, including dihedral angles and hydrogen bond distances, were precisely measured.

    • Main Results:

    • The dihedral angle between the benzene and pyridine rings was determined to be 67.63(8)°.
    • Molecules were observed to form centrosymmetric dimers.
    • A simple intermolecular N-H⋯N hydrogen bond, characterized by the R(2)(2)(8) graph-set motif, was identified as the linking interaction.

    Conclusions:

    • The crystal structure of C(12)H(12)N(2) is characterized by a notable twist between its aromatic rings.
    • The observed dimerization via hydrogen bonding highlights the predictable self-assembly behavior of this compound.
    • These findings contribute to the understanding of structure-property relationships in related organic molecules.