1-Benzyl-1H-benzimidazole
1School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China.
Summary
This study details the crystal structure of a C(14)H(12)N(2) molecule, revealing a planar benzimidazole core. Molecular packing is influenced by C-H⋯N hydrogen bonds and C-H⋯π interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Benzimidazole derivatives are important in medicinal chemistry and materials science.
- Understanding the solid-state structure is crucial for predicting molecular properties and designing new compounds.
Purpose of the Study:
- To elucidate the crystal structure of the title molecule, C(14)H(12)N(2).
- To analyze the intermolecular interactions governing 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 intermolecular interactions (hydrogen bonds, π-π stacking).
Main Results:
- The benzimidazole ring system exhibits near planarity with a root-mean-square deviation of 0.024 Å.
- A significant dihedral angle of 85.77° exists between the imidazole and benzyl rings.
- Crystal packing is characterized by C-H⋯N hydrogen bonds forming chains along the a-axis and C-H⋯π interactions.
Conclusions:
- The detailed crystal structure provides insights into the solid-state behavior of this benzimidazole derivative.
- The identified intermolecular interactions are key to the observed crystal packing and could influence material properties.
More Related Videos
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...
01:37NMR 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...
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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).
01:13Electrophilic 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.
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.