4-Eth-oxy-N-(4-eth-oxy-phen-yl)-N-(4-nitro-phen-yl)aniline
Ming Kong1, Fu-Ying Hao1, Dan-Dan Li1
1Department of Chemistry, Anhui University, Hefei 230039, People's Republic of China, Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 16, 2014
Summary
This study details the molecular structure of C22H22N2O4, revealing specific dihedral angles between its phenyl rings. The crystal structure shows molecules forming a 3D architecture through weak hydrogen bonds and C-H⋯π interactions.
Area of Science:
- Crystallography
- Molecular Chemistry
Background:
- Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
- Organic molecules with nitro and ethoxy-phenyl groups exhibit diverse structural properties.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title molecule C22H22N2O4.
- To analyze the conformational preferences and packing arrangements in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of dihedral angles and intermolecular contacts (C-H⋯O hydrogen bonds, C-H⋯π interactions) was performed.
Main Results:
- The title molecule C22H22N2O4 exhibits specific dihedral angles: 69.31(13)° and 75.90(13)° between ethoxy-phenyl and nitro-phenyl rings.
- A significant dihedral angle of 78.55(13)° was observed between the two ethoxy-phenyl rings.
- Molecules are linked into a 3D supramolecular architecture via weak C-H⋯O hydrogen bonds and C-H⋯π interactions.
Conclusions:
- The study provides detailed structural insights into C22H22N2O4, highlighting its conformational characteristics.
- The identified intermolecular interactions dictate the formation of a 3D supramolecular network in the crystal lattice.
More Related Videos
Related Concept Videos
01:10Nomenclature of Aryl and Heterocyclic Amines
2.2K
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.
2.2K
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
4.3K
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
4.3K
01:17Nomenclature of Primary Amines
3.8K
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.
3.8K
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
5.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.0K
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
3.9K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
3.9K
01:19Diazonium Group Substitution: –OH and –H
1.9K
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.
1.9K