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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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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 constants depend...
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
09:10

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

5-Bromo-1-methyl-indolin-2-one.

Mao-Sen Yuan1, Qi Shuai, Lin Wang

  • 1College of Science, Northwest A&F University, Yangling 712100, Shanxi Province, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study examines the molecular structure of C(9)H(8)BrNO, revealing a near-planar conformation. The research highlights significant pi-electron delocalization within the molecule, particularly involving the N-C=O group.

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Understanding the three-dimensional structure and electronic properties of organic molecules is crucial in drug design and materials science.
  • Indoline derivatives are important scaffolds in medicinal chemistry.

Purpose of the Study:

  • To determine the precise molecular conformation and electronic delocalization in the title compound, C(9)H(8)BrNO.
  • To investigate the extent of pi-electron delocalization within the indoline system.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the molecular structure.
  • Computational methods were used to assess pi-electron delocalization.

Main Results:

  • The title molecule, C(9)H(8)BrNO, exhibits a nearly planar conformation.
  • The inter-planar angle between the benzene and five-membered rings is 1.38(1)°.
  • Pi-electron delocalization is more pronounced in the N-C=O group compared to the N-C-C(benzene) linkage.

Conclusions:

  • The structural and electronic properties of C(9)H(8)BrNO suggest potential for further functionalization and application.
  • The observed pi-delocalization influences the molecule's reactivity and potential interactions.