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6-Bromo-imidazo[1,2-a]pyridin-8-amine
Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
Summary
This study details the crystal structure of a bromine-containing compound, revealing three unique molecules. These molecules exhibit near-planar structures and form hydrogen bonds in their crystalline state.
Area of Science:
- Crystallography
- Chemical Physics
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their properties.
- Brominated nitrogen-containing heterocycles are important in various chemical applications.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(7)H(6)BrN(3).
- To analyze the molecular geometry and intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of molecular planarity and hydrogen bonding networks was performed.
Main Results:
- The compound crystallizes with three independent molecules in the asymmetric unit.
- Molecules are approximately planar, with minor deviations from planarity.
- Primary amine groups exhibit pyramidal coordination.
- Intermolecular N-H⋯N hydrogen bonds link adjacent molecules in the crystal.
Conclusions:
- The crystal structure of C(7)H(6)BrN(3) has been determined.
- The hydrogen bonding patterns provide insights into the compound's solid-state behavior.
- The observed molecular geometry and interactions are characteristic of this class of compounds.
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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).
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 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.
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...
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...
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.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

