Related Experiment Video
Updated: Jun 9, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-(3,5-Di-chloro-4-meth-oxy-phen-yl)acetamide
Rao M Uppu1, Sindhu V Bai1, Patrick F Mensah2
1Department of Environmental Toxicology Southern University and A&M College,Baton Rouge Louisiana 70813 USA.
Iucrdata
|June 8, 2026
Summary
This study details the crystal structure of a dichlorophenyl acetamide compound. Six molecules in the asymmetric unit show similar conformations, linked by hydrogen bonds into chains.
Area of Science:
- Crystallography
- Solid-state chemistry
Background:
- Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
- The specific compound C9H9Cl2NO2 presents an interesting case for structural analysis due to its functional groups.
Purpose of the Study:
- To determine the crystal structure of the title compound C9H9Cl2NO2.
- To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction at 100 K.
- Structure determination using a two-component twin crystal.
- Analysis of molecular geometry and hydrogen bonding networks.
Main Results:
- The compound crystallizes in the triclinic space group P1 with six molecules in the asymmetric unit.
- All six independent molecules exhibit similar conformations, with defined dihedral angles between the dichlorophenyl and acetamide planes (ca. 10.0°) and the methoxy group and aromatic ring (88.5°).
- The extended structure features molecules linked by N-H⋯O hydrogen bonds into infinite chains along [110], forming three distinct alternating molecular motifs (ABABAB, CDCDCD, EFEFEF).
Conclusions:
- The crystal structure reveals a consistent conformational preference for the title compound.
- Intermolecular N-H⋯O hydrogen bonds are the primary drivers for chain formation in the solid state.
- Weak C-H⋯O and C-H⋯Cl interactions further stabilize the crystal packing.
Related Concept Videos
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.
01:16IUPAC Nomenclature of Aldehydes
Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
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...
01:10Nomenclature 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.
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...
01:16Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.