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Published on: February 6, 2020
4-Amino-3-ammonio-pyridinium dinitrate
Madhukar Hemamalini1, Hoong-Kun Fun
1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Summary
The crystal structure of C(5)H(9)N(3) (2+)·2NO(3) (-) reveals a 3D network formed by hydrogen bonds between cations and anions. Pyridinium rings further stabilize this structure through π–π interactions.
Area of Science:
- Crystallography
- Supramolecular Chemistry
Background:
- Understanding the intermolecular forces that dictate crystal packing is crucial in materials science.
- Hydrogen bonding and π–π interactions are key non-covalent forces influencing crystal lattice formation.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(5)H(9)N(3) (2+)·2NO(3) (-).
- To identify and analyze the intermolecular interactions responsible for stabilizing the crystal network.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
- Analysis of the crystal structure involved identifying hydrogen bonds (N-H⋯O, C-H⋯O) and π–π stacking interactions.
Main Results:
- The crystal structure consists of organic cations (C(5)H(9)N(3) (2+)) and nitrate anions (NO(3) (-)).
- A robust three-dimensional network is formed through extensive inter-molecular hydrogen bonds.
- Stabilization of the crystal lattice is further achieved by π–π interactions between adjacent pyridinium rings, with a centroid-centroid distance of 3.775(4) Å.
Conclusions:
- The crystal structure of C(5)H(9)N(3) (2+)·2NO(3) (-) is characterized by a 3D network driven by hydrogen bonding.
- π–π interactions between pyridinium rings play a significant role in the overall crystal stabilization.
Related Concept Videos
01:261° 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...
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...
01:371° 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.
01:19Structure 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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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.
01:12Nomenclature of Secondary and Tertiary Amines
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.