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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-[4-(Morpholinodiazen-yl)phen-yl]acetamide.
Summary
This study details a morpholine-substituted aromatic diazene, C(12)H(16)N(4)O(2). Structural analysis reveals significant π-system conjugation between the diazene and morpholine groups, influencing bond lengths and hybridization.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Aromatic diazenes are versatile organic compounds with applications in various fields.
- Morpholine substituents can significantly alter the electronic and structural properties of aromatic systems.
- Understanding the interplay between substituents and the core aromatic system is crucial for designing novel molecules.
Purpose of the Study:
- To elucidate the detailed molecular structure of a novel morpholine-substituted aromatic diazene (C(12)H(16)N(4)O(2)).
- To investigate the electronic conjugation between the diazene moiety and the morpholine substituent.
- To characterize the conformational preferences and bond characteristics of the title compound.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into electronic conjugation and conformation.
- Spectroscopic methods may have been used for preliminary characterization (though not explicitly stated in the abstract).
Main Results:
- The compound C(12)H(16)N(4)O(2) exhibits significant π-system conjugation, evidenced by altered N=N and N-N bond lengths (1.2707(19) Å and 1.346(2) Å, respectively).
- The morpholine nitrogen atom displays partial sp(2) hybridization, with bond angles ranging from 113.52(14)° to 121.12(14)°.
- The morpholine ring adopts a chair conformation, with the diazenyl group in an equatorial position. Dihedral angles indicate twisting of the diazenyl and acetamido groups relative to the benzene ring.
Conclusions:
- The structural data confirms effective electronic communication between the morpholine nitrogen lone pair and the diazene π-system.
- The observed hybridization and conformational preferences are direct consequences of this electronic conjugation.
- This study provides a detailed structural basis for understanding the properties of morpholine-substituted aromatic diazenes.
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01:11Nomenclature 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.
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.
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.
01:19Diazonium 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.
01:19Amines 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...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
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.
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...