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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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 water loss...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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.
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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Bis(pyridin-2-ylmeth-yl)ammonium nitrate.

Abubak'r Abrahams1, Bernardus van Brecht, Richard Betz

  • 1Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|June 1, 2013
PubMed
Summary

The crystal structure of protonated bis-(pyridin-2-ylmethyl)amine mononitrate reveals specific molecular arrangements. Hydrogen bonds and C-H contacts form a 3D network, detailing intermolecular interactions in this compound.

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Area of Science:

  • Crystal Chemistry
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Bis-(pyridin-2-ylmethyl)amine is a ligand with potential applications in coordination chemistry.
  • Understanding the solid-state structure of its protonated salts is crucial for predicting its behavior in various chemical environments.

Purpose of the Study:

  • To elucidate the crystal structure of bis-(pyridin-2-ylmethyl)amine mononitrate.
  • To analyze the intermolecular interactions, including hydrogen bonding and pi-pi stacking, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of hydrogen bond donors and acceptors was performed to identify specific interactions.

Main Results:

  • The crystal structure of C12H14N3(+)·NO3(-) was determined, showing the protonated amine and nitrate anion.
  • The two pyridine rings within the molecule exhibit a dihedral angle of 7.91°.
  • A three-dimensional network is formed through N-H⋯N, N-H⋯O, C-H⋯N hydrogen bonds, and C-H⋯O contacts.
  • The shortest centroid-centroid distance between aromatic systems is 3.7255 Å.

Conclusions:

  • The study provides a detailed structural characterization of bis-(pyridin-2-ylmethyl)amine mononitrate.
  • The identified hydrogen bonding network highlights the significant role of non-covalent interactions in stabilizing the crystal structure.
  • The findings contribute to the understanding of the solid-state properties of pyridyl-amine derivatives.