Related Experiment Video
Updated: Aug 22, 2025
11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
9.7K
N-(4-Hy-droxy-2-nitro-phen-yl)acetamide
James E Hines Iii1, Curtistine J Deere1, Frank R Fronczek2
1Department of Environmental Toxicology, College of Agriculture, Southern University and A&M College, Baton Rouge, LA 70813, USA.
Iucrdata
|November 7, 2022
Summary
This study examines a nitro compound, C8H8N2O4, revealing unique planarity and hydrogen bonding compared to its isomer. It forms intra- and inter-molecular bonds, creating crystal chains.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- The study focuses on the crystal structure and intermolecular interactions of a specific nitro compound.
- Understanding molecular interactions is crucial for predicting material properties and designing new compounds.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C8H8N2O4.
- To compare its planarity and hydrogen bonding patterns with its 3-nitro isomer.
- To characterize the nature of intra- and inter-molecular hydrogen bonds.
Main Methods:
- Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks within the crystal lattice.
Main Results:
- The title compound exhibits a different degree of planarity compared to the 3-nitro isomer.
- A distinct hydrogen bonding pattern was observed, involving both intra- and inter-molecular interactions.
- The NH group forms an intramolecular hydrogen bond to a nitro oxygen atom.
- The OH group forms an intermolecular hydrogen bond to an amide oxygen atom, leading to the formation of [10] chains.
Conclusions:
- The specific arrangement of hydrogen bonds in the title compound influences its crystal packing and overall structure.
- The observed structural differences highlight the sensitivity of molecular conformation and intermolecular interactions to isomeric variations.
Related Concept Videos
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
4.2K
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.
4.2K
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
4.5K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.5K
01:19Amines to Amides: Acylation of Amines
2.7K
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...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.7K
01:19Diazonium Group Substitution: –OH and –H
2.9K
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.
2.9K
01:28Amides to Carboxylic Acids: Hydrolysis
3.5K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.5K
01:07Acid Halides to Amides: Aminolysis
3.0K
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...
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...
3.0K