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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
2,2,2-Trichloro-N-(3-nitro-phen-yl)acetamide.
A N Prabhu1, V Upadhyaya, K S Girisha
1Physics Department, Manipal Institute of Technology, Manipal University, Manipal 576 104, India.
Acta Crystallographica. Section E, Structure Reports Online
|November 6, 2012
Summary
The crystal structure of a novel nitro-phenyl compound reveals specific molecular arrangements. Hydrogen bonds dictate how these molecules form chains within the crystal lattice, influencing material properties.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding molecular interactions is crucial for designing new materials.
- The specific arrangement of atoms and bonds dictates a compound's physical properties.
- Crystal engineering utilizes intermolecular forces to create ordered structures.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(8)H(5)Cl(3)N(2)O(3).
- To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
- To determine the dihedral angle between the nitro-phenyl ring and the acetamide group.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts.
- Identification and characterization of hydrogen bonding networks.
Main Results:
- The crystal structure of C(8)H(5)Cl(3)N(2)O(3) was successfully determined.
- A small dihedral angle of 5.47(6)° was observed between the nitro-phenyl ring and the acetamide group.
- N-H⋯O and C-H⋯O hydrogen bonds were identified, forming chains parallel to the b axis.
Conclusions:
- The study provides detailed structural information about the title compound.
- The identified hydrogen bonding patterns suggest potential for self-assembly and crystal engineering.
- The findings contribute to the understanding of structure-property relationships in organic crystals.
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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.
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
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.
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.
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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.
01:28Structures 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.
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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.
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