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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.
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
Structures of Carboxylic Acid Derivatives01:28

Structures 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...
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...

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Updated: Jun 1, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Isonicotinonitrile-benzoic acid (1/1).

Li-Jing Cui1, Xin-Yuan Chen

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a 1:1 adduct, revealing a nearly planar arrangement between the carboxyl group and phenyl ring. Molecules form hydrogen bonds and pi-pi interactions, creating a one-dimensional chain structure.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry

Background:

  • Understanding intermolecular interactions is crucial for crystal engineering.
  • The formation of adducts can lead to novel material properties.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a specific 1:1 adduct.
  • To investigate the self-assembly behavior of the molecules in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed.
  • Analysis of hydrogen bonding and π-π interactions was performed.

Main Results:

  • The 1:1 adduct, C(6)H(4)N(2)·C(7)H(6)O(2), exhibits a dihedral angle of 2.05° between the carboxyl group and its phenyl ring.
  • O-H⋯N and C-H⋯O hydrogen bonds form an R(2)(2)(7) ring motif.
  • π-π interactions with centroid-centroid distances of ~3.84-3.91 Å link molecules into a 1D chain along the b axis.

Conclusions:

  • The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking interactions.
  • These interactions direct the formation of a one-dimensional supramolecular chain.
  • The findings contribute to the understanding of molecular self-assembly in crystalline materials.