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Related Concept Videos

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.
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.
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...
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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...

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Related Experiment Video

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

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

Published on: November 23, 2016

2-Hy-droxy-N'-methyl-benzohydrazide.

Xinwen Zhang1

  • 1College of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|September 13, 2012
PubMed
Summary

This study details the molecular structure of C(8)H(10)N(2)O(2), revealing an intramolecular hydrogen bond and specific dihedral angles. Crystal analysis shows molecules forming chains via intermolecular hydrogen bonds and weak C-H⋯π interactions.

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Area of Science:

  • Crystallography
  • Molecular Chemistry
  • Organic Chemistry

Background:

  • Understanding molecular interactions is crucial in chemistry.
  • Hydrogen bonding significantly influences crystal packing and molecular properties.
  • Intramolecular forces dictate a molecule's conformation.

Purpose of the Study:

  • To elucidate the crystal structure of the molecule C(8)H(10)N(2)O(2).
  • To identify and characterize intra- and intermolecular interactions within the crystal lattice.
  • To determine key conformational parameters such as dihedral and torsion angles.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding networks, including N-H⋯N and N-H⋯O interactions.
  • Identification of weak interactions such as C-H⋯π.

Main Results:

  • An intramolecular hydrogen bond was observed between the hydroxyl group and the carbonyl oxygen.
  • The dihedral angle between the benzene ring and amide fragment is 87.16(10)°.
  • The crystal structure exhibits molecular chains formed by N-H⋯N and N-H⋯O hydrogen bonds along the [100] direction.
  • A C-N-N-C torsion angle of 88.87(18)° was measured.
  • Weak C-H⋯π interactions were also identified in the crystal packing.

Conclusions:

  • The molecule C(8)H(10)N(2)O(2) exhibits significant intramolecular hydrogen bonding.
  • Intermolecular hydrogen bonds dictate the formation of one-dimensional chains in the crystal.
  • The determined structural parameters provide insights into the molecule's conformation and solid-state behavior.