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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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2-Hy-droxy-3-nitro-benzaldehyde.

Bei Tang1, Guangying Chen, Xiaoping Song

  • 1Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, Hainan Normal University, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

Researchers isolated a planar compound, C(7)H(5)NO(4), from Actephila merrilliana leaves. Its crystal structure features intramolecular hydrogen bonds and aromatic π-π stacking for stability.

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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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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Area of Science:

  • Natural Product Chemistry
  • Crystallography
  • Organic Chemistry

Background:

  • Plants are a rich source of novel chemical compounds.
  • Understanding molecular structure is key to discovering new properties and applications.

Purpose of the Study:

  • To isolate and characterize a novel compound from Actephila merrilliana.
  • To elucidate the crystal structure and intermolecular interactions of the isolated compound.

Main Methods:

  • Isolation of the title compound (C(7)H(5)NO(4)) from plant leaves.
  • X-ray diffraction analysis to determine crystal structure.
  • Analysis of hydrogen bonding and π-π stacking interactions.

Main Results:

  • The isolated compound C(7)H(5)NO(4) was found to be essentially planar.
  • An intramolecular O-H⋯O hydrogen bond forming an S(6) ring was identified.
  • Crystal packing is stabilized by C-H⋯O interactions and aromatic π-π stacking (3.754 Å).

Conclusions:

  • The planar conformation of C(7)H(5)NO(4) is confirmed by its crystal structure.
  • Specific intermolecular forces dictate the compound's arrangement in the solid state.
  • This structural information provides a basis for further investigation of the compound's properties.