Related Experiment Video
Updated: Jun 1, 2026
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
9,9-Dimethyl-12-phenyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one.
Yong Zhang1, Hong-Jun Zang, Bo-Wen Cheng
1School of Materials and Chemical Engineering, and Key Laboratory of Hollow Fiber Membrane Materials Membrane Process, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China.
Summary
A novel organic compound was synthesized using a three-component coupling reaction. Its crystal structure reveals intermolecular hydrogen bonds and π-π stacking, forming a 3D network.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Three-component coupling reactions offer efficient synthetic routes to complex organic molecules.
- Understanding intermolecular interactions is crucial for predicting and controlling crystal packing.
- Aromatic stacking plays a significant role in the self-assembly of organic materials.
Purpose of the Study:
- To synthesize a novel organic compound with the formula C(25)H(22)O(2).
- To elucidate the crystal structure and supramolecular assembly of the synthesized compound.
- To investigate the role of hydrogen bonding and π-π stacking in the formation of a three-dimensional network.
Main Methods:
- Three-component coupling reaction involving benzaldehyde, 2-naphthol, and 5,5-dimethyl-cyclo-hexane-1,3-dione.
- Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
- Analysis of intermolecular interactions, including hydrogen bonds and π-π stacking.
Main Results:
- Successful synthesis of the title compound, C(25)H(22)O(2).
- Identification of centrosymmetric dimers linked by intermolecular C-H⋯O hydrogen bonds.
- Observation of a three-dimensional network formed by π-π aromatic stacking interactions of the naphthalene ring system (centroid-centroid separation of 3.695(7) Å).
Conclusions:
- The synthesized compound exhibits interesting supramolecular assembly in the solid state.
- Intermolecular hydrogen bonding and π-π stacking are key interactions driving the formation of the 3D crystal network.
- The study provides insights into the crystal engineering of organic molecules through rational design of synthetic precursors.
More Related Videos
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Related Concept Videos
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
01:25Aromatic Compounds: Overview
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
In 1825, Faraday isolated benzene...
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).
01:18Structure of Benzene: Molecular Orbital Model
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
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...