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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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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).
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.7K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.2K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.6K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Updated: May 3, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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2-Bromo-3-hy-droxy-6-methyl-pyridine.

Govind Pratap Singh1, N Rajesh Goud2, P Jeevan Kumar1

  • 1Department of Chemistry, Sri Sathya Sai Institute of Higher Learning, Prasanthinilayam, Ananthapur, Andhra Pradesh, 515 134, India.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
PubMed
Summary

This study details the crystal structure of a brominated pyridine derivative. Molecules form chains via hydrogen bonds, creating 2D networks stabilized by C-H⋯Br interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
  • Pyridine derivatives are important scaffolds in medicinal chemistry and materials science.
  • Intermolecular interactions, such as hydrogen bonding, dictate crystal packing and network formation.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C6H6BrNO.
  • To analyze the molecular geometry and atomic displacements within the crystal lattice.
  • To investigate the intermolecular interactions responsible for crystal packing and network formation.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
  • Analysis of atomic coordinates and bond lengths/angles provided insights into molecular geometry.
  • Hydrogen bond analysis (O-H⋯N and C-H⋯Br) was performed to identify and characterize intermolecular interactions.

Main Results:

  • The crystal structure of C6H6BrNO was successfully determined.
  • The bromine atom showed a displacement of 0.0948(3) Å from the pyridine ring mean plane.
  • Molecules self-assemble into chains along the a-axis via O-H⋯N hydrogen bonds, further organized into 2D networks by C-H⋯Br interactions.

Conclusions:

  • The crystal structure reveals specific atomic displacements influencing molecular conformation.
  • The identified hydrogen bonding patterns (O-H⋯N and C-H⋯Br) are key drivers of the observed supramolecular architecture.
  • The formation of corrugated 2D networks provides insights into the solid-state behavior of this brominated pyridine derivative.