1-(3,3-Dichloro-all-yloxy)-4-methyl-2-nitro-benzene
1Security and Environment Engineering College, Capital University of Economics and Business, Beijing 10070, People's Republic of China.
Summary
This study details the crystal structure of a dichloro-all-yloxy nitrobenzene derivative. Molecular packing is governed by hydrogen bonds and intermolecular interactions, influencing crystal architecture.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding molecular interactions is crucial for predicting material properties.
- Crystal structure analysis reveals the three-dimensional arrangement of atoms and molecules.
- Intermolecular forces dictate the macroscopic properties of crystalline solids.
Purpose of the Study:
- To elucidate the crystal structure of C(10)H(9)Cl(2)NO(3).
- To investigate the intermolecular interactions governing crystal packing.
- To characterize the dihedral angles and bonding in the dichloro-all-yloxy nitrobenzene derivative.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond distances, bond angles, and dihedral angles provided structural insights.
- Identification and analysis of hydrogen bonds, Cl⋯O interactions, and π-π stacking were performed.
Main Results:
- The dihedral angle between the benzene ring and the nitro group plane is 39.1°.
- The dihedral angle between the benzene ring and the dichloro-all-yloxy unit is 40.1°.
- Crystal packing features C-H⋯O hydrogen bonds forming chains, linked by Cl⋯O interactions into sheets, with π-π stacking along the c-axis.
Conclusions:
- The crystal structure is stabilized by a combination of hydrogen bonding, halogen bonding (Cl⋯O), and π-π interactions.
- These intermolecular forces dictate the formation of extended chain and sheet architectures.
- The findings contribute to the understanding of structure-property relationships in organic crystalline materials.
More Related Videos
Related Concept Videos
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
01:13meta-Directing Deactivators: –NO2, –CN, –CHO, –CO2R, –COR, –CO2H
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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...
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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).