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Related Concept Videos

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-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...
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...

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Related Experiment Video

Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

3-Chloro-5-meth-oxy-2,6-dinitro-pyridine.

Jian-Feng Guo1, Jian-Long Wang

  • 1School of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

The crystal structure of C(6)H(4)ClN(3)O(5) reveals significant twisting of its two nitro groups relative to the pyridine ring. These nitro groups exhibit distinct dihedral angles, indicating specific molecular conformations.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Pyridine derivatives are important scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

  • To determine the precise crystal structure of the title compound, C(6)H(4)ClN(3)O(5).
  • To analyze the spatial orientation of the nitro groups relative to the pyridine core.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the molecular structure.
  • Crystallographic data were collected and analyzed to determine atomic positions and bond parameters.

Main Results:

  • The crystal structure of C(6)H(4)ClN(3)O(5) was successfully determined.
  • The two nitro groups attached to the pyridine ring were found to be non-planar, exhibiting significant dihedral angles of 33.12° and 63.66°.
  • These conformational preferences influence the overall molecular geometry.

Conclusions:

  • The determined crystal structure provides detailed insights into the molecular conformation of this pyridine derivative.
  • The observed twisting of nitro groups suggests specific intermolecular interactions and packing arrangements in the solid state.