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Nomenclature of Aryl and Heterocyclic Amines

Nomenclature 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.

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

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...

Nomenclature of Primary Amines

Nomenclature 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.

Diazonium Group Substitution: –OH and –H

Diazonium 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.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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4-Meth-oxy-3-(trifluoro-meth-yl)aniline.

¹College of Chemical and Biological Engineering, Yancheng Institute of Technology, Yinbing Road No. 9 Yancheng, Yancheng 224051, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|February 21, 2012

Summary

This study details the crystal structure of a trifluoromethyl-substituted compound, C(8)H(8)F(3)NO. Intermolecular hydrogen bonds involving nitrogen, fluorine, and carbon atoms stabilize its unique molecular arrangement.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding the molecular structure and intermolecular interactions of organic compounds is crucial for predicting their physical and chemical properties.
The incorporation of fluorine atoms, particularly trifluoromethyl groups, can significantly alter a molecule's electronic properties, lipophilicity, and metabolic stability.
Crystal structure analysis provides fundamental insights into molecular packing and solid-state behavior.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(8)H(8)F(3)NO.
To investigate the role of intermolecular interactions, such as hydrogen bonding, in stabilizing the crystal lattice.
To characterize the spatial orientation of the methoxy group relative to the benzene ring.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional atomic arrangement of the compound.
Crystallographic data were analyzed to identify and quantify bond lengths, bond angles, and intermolecular contacts.
Geometric parameters, including the dihedral angle between the methoxy group and the benzene ring, were precisely measured.

Main Results:

The crystal structure of C(8)H(8)F(3)NO was successfully determined.
The methoxy group was observed to be inclined at an angle of 8.7(4)° to the benzene ring plane.
Intermolecular interactions, specifically N-H⋯F, N-H⋯N, and C-H⋯F hydrogen bonds, were identified as key stabilizing forces within the crystal.

Conclusions:

The crystal packing of C(8)H(8)F(3)NO is significantly influenced by a network of intermolecular hydrogen bonds.
The observed inclination of the methoxy group suggests specific conformational preferences in the solid state.
This structural information is valuable for the design and synthesis of related fluorinated organic molecules with tailored properties.