Related Experiment Video
Updated: Apr 12, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Crystal structure of (E)-pent-2-enoic acid.
Tim Peppel1, Marcel Sonneck1, Anke Spannenberg1
1Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany.
This study reveals the planar structure of a C5H8O2 unsaturated carboxylic acid. Molecules form hydrogen-bonded dimers in the crystal structure, highlighting intermolecular interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the molecular geometry and intermolecular forces of organic compounds is crucial.
- Carboxylic acids are fundamental functional groups in organic chemistry.
Purpose of the Study:
- To determine the crystal structure and molecular conformation of the title compound (C5H8O2).
- To investigate the intermolecular interactions present in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to analyze the crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts.
Main Results:
- The molecule of C5H8O2 was found to be essentially planar, with a maximum atomic displacement of 0.0239(13) Å.
- In the crystal lattice, molecules self-assemble into centrosymmetric dimers.
- These dimers are stabilized by a characteristic pair of O-H⋯O hydrogen bonds.
Conclusions:
- The title compound exhibits a planar molecular geometry in the solid state.
- Intermolecular hydrogen bonding plays a significant role in the crystal packing, leading to dimer formation.
More Related Videos
Related Concept Videos
Structures 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...
IUPAC Nomenclature of Carboxylic Acids
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.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
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.
Ionic Crystal Structures
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...
Naming Enantiomers
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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.

