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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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4-Fluoro-2-[(E)-2-pyridyliminomethyl]phenol.

Ping Cui1, Lei Shi

  • 1Key Laboratory of Anhui Educational Department, Anhui University of Technology, Maanshan 243002, People's Republic of China, and State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China.

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The crystal structure of a fluorinated organic compound reveals a nearly planar conformation. An intramolecular hydrogen bond significantly stabilizes this molecular arrangement.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular conformation is crucial in predicting chemical properties and reactivity.
  • Intramolecular interactions play a key role in defining the three-dimensional structure of organic molecules.
  • Fluorinated organic compounds exhibit unique electronic and physical properties.

Purpose of the Study:

  • To elucidate the crystal structure and molecular conformation of the title compound C(12)H(9)FN(2)O.
  • To investigate the nature and influence of intramolecular interactions on the molecular geometry.
  • To provide a detailed structural analysis of this specific fluorinated organic molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
  • Intermolecular and intramolecular interactions, including hydrogen bonding, were identified and analyzed.

Main Results:

  • The crystal structure of C(12)H(9)FN(2)O was successfully determined.
  • A dihedral angle of 4.35(16)° between the benzene and pyridine rings indicates a nearly planar conformation.
  • An intramolecular O-H⋯N hydrogen bond was identified as a key stabilizing factor.

Conclusions:

  • The title compound adopts a conformation with minimal deviation from planarity between its aromatic rings.
  • Intramolecular hydrogen bonding is a significant force in dictating the observed molecular structure.
  • The detailed structural data provides a foundation for further studies on the properties and applications of this compound.