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-(2,4-Dimethyl-phen-yl)-2-methyl-benzamide
Summary
This study details the molecular structure of a novel organic compound, C(16)H(17)NO. Researchers found specific bond conformations and crystal packing, revealing insights into its chemical properties and potential applications.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their chemical behavior.
- Conformational analysis and crystal packing provide fundamental insights into intermolecular interactions.
Purpose of the Study:
- To elucidate the detailed molecular structure of the title compound, C(16)H(17)NO.
- To investigate the conformational preferences of the N-H bond and the relative orientation of the aromatic rings.
- To characterize the hydrogen bonding interactions and crystal packing in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise atomic arrangement.
- Analysis of bond lengths, bond angles, and dihedral angles provided conformational information.
- Intermolecular interactions, specifically hydrogen bonding, were identified and analyzed.
Main Results:
- The N-H bond was observed in an anti conformation relative to the C=O bonds.
- The aniline and benzoyl rings exhibited near-coplanarity with a small dihedral angle of 4.9°.
- The amide group plane formed significant angles with both aromatic rings (61.3° and 58.3°).
- Molecules were arranged into chains along the b axis via N-H⋯O hydrogen bonds.
Conclusions:
- The study provides a comprehensive structural characterization of C(16)H(17)NO.
- The observed conformation and hydrogen bonding pattern are key features influencing the compound's solid-state properties.
- This structural data serves as a foundation for further investigations into the compound's reactivity and potential applications.
More Related Videos
Related Concept Videos
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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...
01:23Nomenclature 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).
01:19Diazonium 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.
01:37NMR 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...
01:17Nomenclature 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.