Related Experiment Video
Updated: Jun 1, 2026

10:44
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
4,4'-(1,1,1,3,3,3-Hexafluoro-propane-2,2-diyl)dibenzoic acid
Summary
The crystal structure of a novel organic compound reveals twisted benzene rings and a unique wave-like layered arrangement. This supramolecular architecture is formed through specific hydrogen bonding interactions between molecules.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding the three-dimensional arrangement of molecules in crystals is crucial for predicting material properties.
- Hydrogen bonding plays a significant role in the self-assembly of organic compounds into ordered structures.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(17)H(10)F(6)O(4).
- To investigate the intermolecular interactions and supramolecular assembly in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks (O-H⋯O and C-H⋯F) and dihedral angles between aromatic rings.
Main Results:
- The crystal structure of C(17)H(10)F(6)O(4) was determined, revealing a significant dihedral angle of 67.43° between the two benzene rings.
- Adjacent molecules form a wave-like layered supramolecular structure mediated by O-H⋯O and C-H⋯F hydrogen bonds.
Conclusions:
- The study provides detailed structural insights into the packing of C(17)H(10)F(6)O(4) in the solid state.
- The observed supramolecular arrangement highlights the importance of specific hydrogen bonding in dictating crystal architecture.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
π Molecular Orbitals of 1,3-Butadiene
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Hybridization of Atomic Orbitals I
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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 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.
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.
VSEPR Theory and the Basic Shapes
Overview of VSEPR Theory
