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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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3,3-Dichloro-1-(chloro-meth-yl)indolin-2-one.

Yao Wang1, Chong-Qing Wan, Tingting Zheng

  • 1Department of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

This study details the crystal structure of a trichlorinated pyrrole-benzene compound. Molecular interactions, including chlorine-chlorine bonds and pi-pi stacking, form a unique two-dimensional network in the solid state.

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Area of Science:

  • Crystal Engineering
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding intermolecular forces is crucial for designing novel materials.
  • The pyrrole and benzene moieties are common scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a novel C(9)H(6)Cl(3)NO compound.
  • To investigate the self-assembly behavior driven by halogen bonding and pi-pi interactions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond distances, bond angles, and torsion angles provided insights into molecular conformation.
  • Intermolecular interactions, including Cl...Cl, C-H...O, and pi-pi interactions, were identified and quantified.

Main Results:

  • The pyrrole and benzene rings exhibit near-coplanarity with a dihedral angle of 1.90(9)°.
  • A significant Cl-C-N-C torsion angle of 98.78(17)° was observed.
  • Dimeric structures formed via Cl...Cl interactions (3.564(5) Å) were identified.
  • These dimers further assembled into a 2D network through C-H...O and pi-pi interactions (centroid-centroid distances of ~4.1-4.2 Å).

Conclusions:

  • The crystal packing is dominated by a combination of halogen bonding and pi-pi stacking interactions.
  • The observed 2D network structure offers potential for applications in materials science.
  • This study provides a detailed understanding of the supramolecular assembly in this halogenated organic compound.