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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

Phase II Reactions: Acetylation Reactions

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Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Nomenclature of Aryl and Heterocyclic Amines

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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.

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Summary

This summary is machine-generated.

This study details the molecular structure of C(8)H(8)ClNO, revealing anti conformations for N-H and C=O bonds and syn conformations for C-Cl and C=O bonds. Molecules self-assemble into infinite chains via N-H⋯O hydrogen bonds.

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Area of Science:

Crystallography
Molecular Chemistry

Background:

Understanding molecular conformation and intermolecular interactions is crucial in chemical and pharmaceutical sciences.
Crystal structure analysis provides fundamental insights into molecular arrangement and bonding.

Purpose of the Study:

To elucidate the specific molecular conformation and hydrogen bonding patterns in the title compound, C(8)H(8)ClNO.
To characterize the supramolecular assembly of C(8)H(8)ClNO in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of bond orientations and intermolecular interactions, specifically hydrogen bonding, was performed.

Main Results:

The study identified anti conformations between the N-H and C=O bonds.
Syn conformations were observed between the C-Cl and C=O bonds within the side chain.
Molecules were found to form infinite chains through N-H⋯O hydrogen bonds along the [101] crystallographic direction.

Conclusions:

The specific conformational preferences and hydrogen bonding network dictate the crystal packing of C(8)H(8)ClNO.
The observed chain-like supramolecular structure is a direct consequence of these intermolecular forces.