Related Experiment Video
Updated: Jun 1, 2026
11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
N-(2,6-Dimethyl-phen-yl)-3-methyl-benzamide
Summary
The molecular structure reveals anti N-H and C=O bonds, with aromatic rings at a 73.3° dihedral angle. Intermolecular hydrogen bonds form chains in the crystal structure.
Area of Science:
- Crystallography
- Molecular Structure Analysis
- Organic Chemistry
Background:
- Understanding the precise three-dimensional arrangement of atoms within a molecule is crucial for predicting its chemical and physical properties.
- Crystal structure analysis provides detailed insights into intermolecular interactions and solid-state packing.
Purpose of the Study:
- To elucidate the detailed molecular and crystal structure of the title compound, C(16)H(17)NO.
- To investigate the spatial relationship between key functional groups and the packing of molecules in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonds) was performed.
Main Results:
- The molecular structure exhibits an anti conformation between the N-H and C=O bonds.
- The two aromatic rings display a significant dihedral angle of 73.3(1)°.
- Intermolecular N-H⋯O hydrogen bonds were identified, linking molecules into C(4) chains along the crystallographic c axis.
Conclusions:
- The determined crystal structure provides a precise description of the title compound's solid-state organization.
- The observed intermolecular hydrogen bonding pattern dictates the formation of characteristic chain structures in the crystal lattice.
- This structural information is fundamental for further studies on the compound's reactivity and material properties.
Related Concept Videos
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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.
01:11Nucleophilic 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...
01:20Electrophilic 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.