1-Iodo-4-meth-oxy-2-nitro-benzene.
Acta Crystallographica. Section E, Structure Reports Online
|March 14, 2012
Summary
This study details the crystal structure of a novel organic compound, revealing planar molecular geometry and significant intra- and inter-molecular iodine-oxygen interactions. These interactions facilitate the formation of zigzag chains and layered structures, crucial for understanding material properties.
Area of Science:
- Crystallography
- Solid-state chemistry
- Supramolecular chemistry
Background:
- Understanding the packing of organic molecules is essential for predicting material properties.
- Halogen bonding, particularly involving iodine, plays a significant role in crystal engineering.
- Non-covalent interactions dictate the assembly of molecular structures in the solid state.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(7)H(6)INO(3).
- To investigate the nature and significance of intra- and inter-molecular interactions within the crystal lattice.
- To characterize the self-assembly process leading to the observed supramolecular architecture.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular distances was performed.
- Computational methods were used to analyze non-covalent interactions, including halogen bonding and pi-pi stacking.
Main Results:
- The 12 non-hydrogen atoms of the title compound exhibit planar geometry with a root-mean-square deviation of 0.016 Å.
- A notable intra-molecular iodine-oxygen (I⋯O) interaction of 3.0295(13) Å was identified.
- Inter-molecular I⋯O interactions of 3.3448(13) Å result in the formation of zigzag chains along the b-axis, further organized into layers by π-π interactions.
Conclusions:
- The crystal structure is characterized by a combination of intra- and inter-molecular interactions, including significant halogen bonding.
- The observed supramolecular assembly, featuring zigzag chains and layered structures, is driven by I⋯O and π-π interactions.
- The findings provide insights into the structure-property relationships of iodine-containing organic compounds and their potential applications in materials science.
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.
01:13Electrophilic 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...
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...
01:11ortho–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...