Related Experiment Video
Updated: Jun 1, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Bis[4-(2-benzyl-idenepropyl-idene-amino)phen-yl] ether
Summary
A novel Schiff base, C(32)H(28)N(2)O, was synthesized with high yield. Crystallographic analysis revealed its trans configuration, molecular shape, and specific dihedral angle, providing insights into its structural properties.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding the structure-property relationships of Schiff bases is crucial for materials design.
- The synthesis and characterization of novel Schiff bases contribute to fundamental chemical knowledge.
Purpose of the Study:
- To synthesize and characterize a novel Schiff base compound.
- To determine the molecular and crystal structure of the synthesized Schiff base.
- To investigate the structural features, including configuration and dihedral angles, of the Schiff base.
Main Methods:
- High-yield synthesis via condensation reaction of α-methyl-cinnamaldehyde and bis-(4-amino-phen-yl) ether.
- Single-crystal X-ray diffraction for crystallographic analysis.
- Analysis of crystallographic data to determine cell parameters, molecular conformation, and twinning.
Main Results:
- The Schiff base C(32)H(28)N(2)O was successfully synthesized in high yield.
- The compound exhibits a trans configuration across the C=N double bond.
- Crystallographic analysis revealed pseudo-ortho-rhom-bic cell parameters and merohedral twinning, with a refined twin domain fraction of 0.722(1).
- The elongated elementary cell shape reflects the molecular geometry, and the dihedral angle between O-linked aromatic rings is 57.86(8)°.
Conclusions:
- The study successfully synthesized and structurally characterized a novel flexible Schiff base.
- The determined crystal structure provides valuable information on the molecule's conformation and packing.
- The findings contribute to the understanding of Schiff base chemistry and their structural diversity.
Related Concept Videos
02:28Structure and Nomenclature of Ethers
Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
02:36Crown Ethers
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
02:38Structure and Nomenclature of Epoxides
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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).
01:11Nomenclature 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...
01:37NMR 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...