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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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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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NMR Spectroscopy of Benzene Derivatives01:34

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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...
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Dopamine receptor antagonists, also known as antipsychotic agents, are critical in managing chemotherapy-induced vomiting. These antiemetic agents block dopamine receptors in the chemoreceptor trigger zone (CTZ), inhibiting signal transmission to the vomiting center. Antipsychotic agents encompass phenothiazines (PTZ), butyrophenones, benzamides, and thienobenzodiazepines (Zyprexa), which are utilized for their antiemetic and sedative properties.
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Physical Properties of Amines

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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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2-Nitro-N-propyl-benzamide.

Li-Hua Guo1, Hai-Jun Tan, Ji-Kui Wang

  • 1Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

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

This study details the crystal structure of a compound with the chemical formula C(10)H(12)N(2)O(3). The molecules form chains through hydrogen bonding and are further stabilized by C-H interactions.

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Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
  • Molecular interactions, such as hydrogen bonding and van der Waals forces, dictate crystal packing and material characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(10)H(12)N(2)O(3).
  • To identify and analyze the intermolecular interactions responsible for the observed crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
  • Analysis of bond lengths, bond angles, and intermolecular contacts was performed.

Main Results:

  • The asymmetric unit contains three molecules of C(10)H(12)N(2)O(3).
  • Intermolecular N-H⋯O hydrogen bonds link the molecules into chains propagating along the b-axis.
  • Weak C-H⋯π interactions further stabilize the crystal lattice.

Conclusions:

  • The crystal structure of C(10)H(12)N(2)O(3) is characterized by a chain-like arrangement driven by N-H⋯O hydrogen bonds.
  • The interplay of hydrogen bonding and C-H⋯π interactions governs the overall crystal packing and stability.