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

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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...
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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2,5-Di-meth-oxy-benzo-nitrile.

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This study reveals the crystal structure of C9H9NO2, detailing molecular arrangement through hydrogen bonding and pi-pi stacking. These interactions form polymeric strands, offering insights into crystal engineering and molecular assembly.

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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Understanding molecular packing is crucial for predicting material properties.
  • Intermolecular interactions, such as hydrogen bonding and pi-pi stacking, dictate crystal structures.
  • The specific compound C9H9NO2 has potential applications influenced by its solid-state arrangement.

Purpose of the Study:

  • To elucidate the crystal structure of the molecule C9H9NO2.
  • To investigate the intermolecular interactions governing its solid-state organization.
  • To characterize the packing motifs and their influence on the overall crystal architecture.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of non-hydrogen atom deviations from planarity.
  • Identification and quantification of intermolecular interactions, including C-H···O, C-H···N hydrogen bonds, and pi-pi stacking.

Main Results:

  • The non-hydrogen atoms of C9H9NO2 exhibit near-planarity with minor deviations.
  • Molecules form centrosymmetric pairs stabilized by C-H···O and C-H···N interactions.
  • Pi-pi stacking between benzene rings leads to polymeric strands along the a-axis, with a specific centroid-centroid distance of 3.91001(15) Å.
  • A step of 0.644(2) Å exists between planar parts of centrosymmetric pairs.
  • Aromatic rings in neighboring strands are tilted by 29.08(2)° due to n-glide operations.

Conclusions:

  • The crystal structure of C9H9NO2 is characterized by a combination of hydrogen bonding and pi-pi stacking.
  • These interactions result in a specific polymeric arrangement of molecules in the solid state.
  • The detailed structural analysis provides a foundation for understanding the physical and chemical properties of C9H9NO2.