Related Experiment Video
Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-(2-Fluoro-benzoyl-meth-yl)benzoic acid
Summary
This study details the crystal structure of a fluorinated organic compound, C(15)H(11)FO(3). It reveals specific molecular orientations and intermolecular interactions like hydrogen bonds and C-H⋯π contacts influencing crystal packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the three-dimensional arrangement of molecules in crystals is crucial for predicting material properties.
- Intermolecular forces, such as hydrogen bonds and van der Waals interactions, dictate crystal packing and stability.
- Fluorinated organic compounds exhibit unique electronic and physical properties due to the electronegativity of fluorine.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(15)H(11)FO(3).
- To analyze the specific molecular orientations and intermolecular interactions present in the crystal lattice.
- To understand how these interactions contribute to the overall crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of the crystal structure involved identifying hydrogen bonds (O-H⋯O, C-H⋯O) and C-H⋯π interactions.
- Dihedral angles between aromatic rings were measured to quantify their relative orientation.
Main Results:
- The crystal structure of C(15)H(11)FO(3) was successfully determined.
- A significant dihedral angle of 69.26(3)° was observed between the aromatic rings.
- Inversion dimers were identified, stabilized by intermolecular O-H⋯O hydrogen bonds.
- C-H⋯O hydrogen bonds and C-H⋯π contacts between specific aromatic rings were found to further stabilize the crystal packing.
Conclusions:
- The crystal structure of C(15)H(11)FO(3) is characterized by a specific dihedral angle between aromatic rings.
- Intermolecular hydrogen bonding and C-H⋯π interactions play a critical role in the observed crystal packing.
- These findings contribute to the understanding of structure-property relationships in fluorinated organic compounds.
Related Concept Videos
01:16IUPAC 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...
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
01:22Electrophilic Aromatic Substitution: Sulfonation of Benzene
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
01:15Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...