Related Experiment Video
Updated: May 7, 2026
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
2-Meth-oxy-4-(prop-2-en-1-yl)phenyl benzoate
Mallikarjuna Rao Pichika1, Yew Beng Kang, Seik Weng Ng
1Department of Pharmaceutical Chemistry, International Medical University, 126 Jalan Bukit Jalil, 57000 Kuala Lumpur, Malaysia.
Acta Crystallographica. Section E, Structure Reports Online
|September 19, 2013
Summary
The crystal structure of a C17H16O3 compound reveals significant benzene ring twisting, comparable to phenyl benzoate. This molecular arrangement is stabilized by C-H⋯O hydrogen bonds in its crystal packing.
Area of Science:
- Organic Chemistry
- Crystallography
Background:
- Understanding the conformational preferences of organic molecules is crucial in chemistry.
- Phenyl benzoate serves as a reference compound for studying benzene ring orientations.
Purpose of the Study:
- To characterize the crystal structure of the title compound (C17H16O3).
- To compare the observed benzene ring twist angle with that of phenyl benzoate.
- To investigate intermolecular interactions in the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and torsion angles provided conformational details.
- Intermolecular interactions were identified through hydrogen bond analysis.
Main Results:
- The title compound, C17H16O3, exhibits a significant twist between its benzene rings, measured at 63.54(5)°.
- This observed twist angle is comparable to the twist angle found in unsubstituted phenyl benzoate.
- Crystal packing analysis revealed the presence of C-H⋯O hydrogen bonds contributing to the structural stability.
Conclusions:
- The conformational flexibility of the C17H16O3 molecule allows for substantial twisting of its aromatic rings.
- The structural similarity in benzene ring twist between C17H16O3 and phenyl benzoate suggests common electronic or steric influences.
- C-H⋯O hydrogen bonds play a role in organizing the molecular packing in the solid state.
More Related Videos
Related Concept Videos
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
00:59Reactions at the Benzylic Position: Oxidation and Reduction
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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).
01:27Benzene to Phenol via Cumene: Hock Process
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...