Related Experiment Video
Updated: May 13, 2026
06:18
Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
N,N'-(Pyridine-2,6-di-yl)dibenzamide.
Parisa Mahboubi Anarjan1, Nader Noshiranzadeh, Rahman Bikas
1Sama Technical and Vocational Training College, Islamic Azad University, Mamaghan Branch, Mamaghan, Iran.
Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
Summary
This study details the crystal structure of C19H15N3O2, revealing a nearly planar molecule with hydrogen bonds forming a 2D array. The findings offer insights into molecular arrangement in crystalline solids.
Area of Science:
- Crystallography
- Solid-state chemistry
- Molecular structure determination
Background:
- Understanding molecular arrangement is crucial in solid-state chemistry.
- Crystallographic symmetry and intermolecular forces dictate crystal packing.
Purpose of the Study:
- To elucidate the crystal structure of the title compound (C19H15N3O2).
- To analyze the molecular geometry and intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of crystallographic twofold symmetry and hydrogen bonding patterns.
Main Results:
- The molecule C19H15N3O2 exhibits approximate planarity, with a dihedral angle of 7.53° between pyridine and benzene rings.
- The crystal structure is characterized by N-H⋯O hydrogen bonds, forming a two-dimensional array perpendicular to the c axis.
- The pyridine nitrogen atom is situated on a crystallographic twofold rotation axis.
Conclusions:
- The crystal packing of C19H15N3O2 is governed by hydrogen bonding and crystallographic symmetry.
- The study provides a detailed structural characterization of this organic compound in the solid state.
More Related Videos
Related Concept Videos
01:25Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
01:19Diazonium 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.
01:18Basicity of Aromatic Amines
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
01:11Nucleophilic 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...
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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...