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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).
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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.
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.
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...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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4,6-Dimethyl-pyrimidin-2-amine.

Wei-Wei Fu1, Yang Liu, Geng Huang

  • 1Key Laboratory of Functional Organometallic Materials of General Colleges and Universities in Hunan Province, Department of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structure of C6H9N3, detailing three independent, nearly planar molecules. These molecules form zigzag ribbons through N-H⋯N hydrogen bonds in the crystal lattice.

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Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding molecular geometry and intermolecular interactions is crucial in chemical physics.
  • Crystal structure analysis provides fundamental insights into solid-state properties.
  • Hydrogen bonding plays a significant role in molecular assembly and material characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C6H9N3.
  • To analyze the molecular geometry and planarity of independent molecules within the asymmetric unit.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, that govern the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of the asymmetric unit revealed three independent molecules.
  • Geometric parameters, including root-mean-square (r.m.s.) deviations from planarity, were calculated.
  • Hydrogen bonding networks and their topological descriptors (graph-set motifs) were identified.

Main Results:

  • The asymmetric unit of C6H9N3 contains three crystallographically independent molecules.
  • All three molecules exhibit near-planar geometry, with low r.m.s. deviations (0.003, 0.016, and 0.005 Å).
  • Intermolecular N-H⋯N hydrogen bonds link the molecules into zigzag ribbons oriented along the c axis.
  • These ribbons form a specific supramolecular arrangement characterized by the R2(2)(8) graph-set motif.

Conclusions:

  • The crystal structure of C6H9N3 is characterized by multiple independent, planar molecules.
  • Hydrogen bonding is the primary driving force for the formation of one-dimensional zigzag ribbons.
  • The identified R2(2)(8) graph-set motif provides a detailed description of the hydrogen-bonding network in the solid state.