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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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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...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.3K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1.9K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
1.9K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

3.7K
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...
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1-(2,4-Di-nitro-phen-yl)-2-[(E)-2,4,5-tri-meth-oxy-benzyl-idene]hydrazine.

Hoong-Kun Fun1, Suchada Chantrapromma, Boonlerd Nilwanna

  • 1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online
|October 11, 2013
PubMed
Summary

This study details the crystal structure of a C16H16N4O7 compound, revealing near-planar geometry and specific intramolecular and intermolecular interactions. These findings contribute to understanding molecular packing and hydrogen bonding in organic crystals.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular structure and intermolecular forces is crucial for predicting material properties.
  • C16H16N4O7 is a compound with potential applications in various chemical fields.
  • Previous studies may not have fully elucidated the detailed crystal packing and bonding of this specific molecule.

Purpose of the Study:

  • To determine the precise three-dimensional crystal structure of the title compound C16H16N4O7.
  • To analyze the planarity, substituent group orientations, and hydrogen bonding network within the crystal lattice.
  • To investigate the intermolecular interactions, including π-π stacking, that govern crystal assembly.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.
  • Crystallographic software was used for structure solution and refinement.
  • Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts was performed.

Main Results:

  • The compound exhibits a near-planar molecular conformation with a dihedral angle of 3.15° between benzene rings.
  • Methoxy and nitro groups show varying degrees of coplanarity with their attached rings.
  • An intramolecular N-H⋯O hydrogen bond forms an S(6) ring, and intermolecular N-H⋯O bonds create R2(2)(12) loops in inversion dimers.
  • Crystal packing is further stabilized by C-H⋯O interactions forming sheets and π-π stacking with a centroid-centroid distance of 3.5974 Å.

Conclusions:

  • The detailed crystal structure of C16H16N4O7 has been elucidated.
  • The study highlights the interplay of intramolecular and intermolecular forces in dictating molecular conformation and crystal packing.
  • The identified hydrogen bonding and π-π stacking interactions provide insights into the solid-state behavior of this organic compound.