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Related Concept Videos

Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium 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.
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature 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.
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...

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Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-<i>N</i>'-benzyl-idene-4-chloro-benzene-sulfono-hydrazide and of its (<i>E</i>)-4-chloro-<i>N</i>'-(<i>ortho</i>- and <i>para</i>-methyl-benzyl-idene)benzene-sulfono-hydrazide derivatives.

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Related Experiment Video

Updated: May 27, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

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N,N'-Bis(3-chloro-phen-yl)malonamide.

Vinola Z Rodrigues, Sabine Foro, B Thimme Gowda

    Acta Crystallographica. Section E, Structure Reports Online
    |November 8, 2011
    PubMed
    Summary

    This study details the crystal structure of a dichloro-diamide compound, C(15)H(12)Cl(2)N(2)O(2). It reveals specific molecular orientations and intermolecular hydrogen bonding critical for crystal packing.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Crystal structure analysis provides precise details on molecular conformation, intermolecular interactions, and packing in the solid state.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(15)H(12)Cl(2)N(2)O(2).
    • To investigate the conformational preferences of the amide and phenyl rings and the influence of chloro substituents.
    • To identify and characterize intermolecular interactions, such as hydrogen bonding, within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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  • Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts was performed.
  • The crystallographic asymmetric unit was analyzed to understand the symmetry and arrangement of independent molecules.

    • Main Results:

    • The asymmetric unit contains two independent molecules of C(15)H(12)Cl(2)N(2)O(2).
    • Specific anti and syn orientations of amide N-H bonds relative to meta-chloro groups were observed in both molecules.
    • Amide groups exhibit near-coplanarity with adjacent phenyl rings (dihedral angles ~9-11°), while amide planes are nearly perpendicular to each other (dihedral angles ~83-87°).
    • Intermolecular N-H⋯O hydrogen bonds link molecules into chains in the crystal.

    Conclusions:

    • The crystal structure of C(15)H(12)Cl(2)N(2)O(2) is characterized by specific conformational arrangements and intermolecular hydrogen bonding.
    • The observed hydrogen bonding network plays a significant role in the crystal packing and stabilization.
    • The findings contribute to the understanding of structure-property relationships in related organic compounds.