1,4-Bis(4-amino-phen-oxy)benzene
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details a precursor molecule for polyimide synthesis. Its unique molecular structure is stabilized by intermolecular hydrogen bonds, influencing its material properties.
Area of Science:
- Materials Science
- Crystallography
- Organic Chemistry
Background:
- Polyimides are advanced polymers with significant applications in electronics and aerospace.
- Understanding the molecular structure of precursors is crucial for designing novel polyimide materials.
- Crystallographic studies provide fundamental insights into molecular conformation and intermolecular interactions.
Purpose of the Study:
- To characterize the molecular structure and conformation of a novel polyimide precursor.
- To investigate the intermolecular interactions stabilizing the crystal structure.
- To provide data relevant for the synthesis of advanced polyimides.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
- Analysis of crystallographic data revealed the molecular geometry and symmetry.
- Intermolecular interactions, specifically hydrogen bonding, were identified and analyzed.
Main Results:
- The title compound, C(18)H(16)N(2)O(2), was synthesized and characterized.
- The molecule resides on a crystallographic inversion center, exhibiting high symmetry.
- Terminal amino-phenoxy rings are nearly perpendicular to the central benzene ring (dihedral angle of 85.40(4)°).
- The crystal packing is stabilized by N-H⋯O and N-H⋯N intermolecular hydrogen bonds.
Conclusions:
- The determined molecular conformation and hydrogen bonding patterns are key features of this polyimide precursor.
- This structural information is vital for predicting and controlling the properties of derived polyimides.
- The findings contribute to the rational design of new high-performance polymers.
Related Concept Videos
NMR 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...
Benzene 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...
Nomenclature 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).
Hydrolysis 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...
Reactions 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.
Structure 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).


