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Related Concept Videos

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...
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.
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.
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.
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...

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

3-Acet-oxy-2-naphthoic acid.

Bruno S Souza, Ramon Vitto, Faruk Nome

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a naphthalene analog of acetyl-salicylic acid. Molecular geometry and intermolecular interactions, including hydrogen bonding, were analyzed.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Materials Science

    Background:

    • Acetyl-salicylic acid (aspirin) is a widely used pharmaceutical.
    • Naphthalene derivatives are explored for diverse chemical properties.
    • Understanding molecular structure influences material properties and drug design.

    Purpose of the Study:

    • To elucidate the crystal structure and molecular geometry of a naphthalene analog of acetyl-salicylic acid.
    • To investigate intermolecular interactions, including hydrogen bonding and crystal packing.
    • To provide insights into the structure-property relationships of this compound.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles characterized the molecular conformation.

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  • Intermolecular interactions, such as hydrogen bonds and van der Waals forces, were identified and analyzed.

    • Main Results:

    • The naphthalene unit exhibits slight twisting due to ortho disubstitution (dihedral angle = 2.0°).
    • Carboxylic and ester groups are nearly coplanar and perpendicular, respectively, to the naphthalene system (dihedral angles 8.9° and 89.3°).
    • Molecules form centrosymmetric dimers via carboxylic O-H⋯O hydrogen bonds (R2(2)(8) motif), with additional weak C-H⋯O contacts observed. Crystal stacking occurs along [100] and [010] directions.

    Conclusions:

    • The study provides a detailed structural characterization of the naphthalene analog.
    • The observed hydrogen bonding and crystal packing influence the solid-state properties.
    • This structural data can inform the design of related compounds with tailored functionalities.