Related Experiment Video
Updated: May 18, 2026
11:45
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
1-[Bis(4-fluoro-phen-yl)meth-yl]piperazine
Acta Crystallographica. Section E, Structure Reports Online
|September 13, 2012
Summary
This study details the molecular structure of C(17)H(18)F(2)N(2), revealing a significant dihedral angle between its benzene rings. The piperazine ring adopts a chair conformation, with hydrogen bonds observed in the crystal structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Fluorinated organic compounds and piperazine derivatives are important scaffolds in medicinal chemistry and materials science.
Purpose of the Study:
- To elucidate the precise molecular geometry and crystal packing of the title compound, C(17)H(18)F(2)N(2).
- To characterize the conformation of the piperazine ring and identify intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided detailed geometric information.
Main Results:
- The dihedral angle between the two benzene rings in C(17)H(18)F(2)N(2) was determined to be 73.40(3)°.
- The piperazine ring adopts a chair conformation with the N-H hydrogen atom in an equatorial position.
- Weak C-H⋯F hydrogen bonds were identified as the primary intermolecular interactions, linking molecules in the crystal.
Conclusions:
- The study provides a detailed structural characterization of C(17)H(18)F(2)N(2), highlighting its specific conformational preferences.
- The observed hydrogen bonding network offers insights into the solid-state behavior and potential intermolecular interactions of this fluorinated piperazine derivative.
Related Concept Videos
01:25Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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.
01:11Nomenclature 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...