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Related Concept Videos

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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature 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.
IUPAC Nomenclature of Carboxylic Acids01:16

IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
IUPAC Nomenclature of Aldehydes01:16

IUPAC 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...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Published on: January 19, 2016

Isonicotinonitrile-4-methyl-benzoic acid (1/1).

Xing-Wei Cai1, Hong-Fei Lu

  • 1School of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|July 15, 2011
PubMed
Summary

This study describes a new co-crystal formed by isonicotinonitrile and 4-methyl-benzoic acid. The crystal structure reveals planar molecules linked by hydrogen bonds and stabilized by π-π stacking interactions.

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Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Co-crystals offer tunable material properties.
  • Understanding intermolecular interactions is key to crystal design.
  • Isonicotinonitrile and 4-methyl-benzoic acid are suitable building blocks for co-crystals.

Purpose of the Study:

  • To synthesize and characterize a novel co-crystal of isonicotinonitrile and 4-methyl-benzoic acid.
  • To investigate the intermolecular interactions governing the crystal structure.
  • To explore the potential of these molecules in co-crystal formation.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the crystal structure.
  • Analysis of hydrogen bonding (O-H⋯N, C-H⋯O) and π-π stacking interactions.
  • Calculation of molecular planarity and dihedral angles.

Main Results:

  • A co-crystal with the formula C(6)H(4)N(2)·C(8)H(8)O(2) was successfully synthesized.
  • The crystal structure consists of planar isonicotinonitrile and 4-methyl-benzoic acid molecules.
  • Molecules are linked by O-H⋯N and C-H⋯O hydrogen bonds, forming a nearly coplanar arrangement with a dihedral angle of 2.48°.
  • Slipped π-π stacking interactions (centroid-centroid distance 3.6797 Å) and C-H⋯N interactions further stabilize the crystal.

Conclusions:

  • The synthesized co-crystal exhibits a well-defined structure stabilized by a combination of hydrogen bonding and π-π stacking.
  • The planar nature of the components and their specific arrangement contribute to the crystal's stability.
  • This work provides insights into the supramolecular assembly of isonicotinonitrile and 4-methyl-benzoic acid, relevant for crystal engineering.