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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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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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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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4-Bromo-N-(2-nitro-phen-yl)benzamide.

Rodolfo Moreno-Fuquen1, Alexis Azcárate1, Alan R Kennedy2

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This study details the crystal structure of nitro-phenyl benzamide, revealing specific molecular arrangements and weak interactions. These interactions, including hydrogen and halogen bonds, influence the compound's crystal packing and supramolecular assembly.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Nitro-phenyl benzamide is an organic compound with potential applications in materials science.
  • Understanding the crystal structure is crucial for predicting and controlling material properties.

Purpose of the Study:

  • To elucidate the crystal structure of nitro-phenyl benzamide.
  • To analyze the intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and non-covalent interactions was performed.

Main Results:

  • The asymmetric unit contains two molecules of nitro-phenyl benzamide (C13H9BrN2O3).
  • Dihedral angles between benzene rings range from 16.78(15)° to 18.87(14)°.
  • Intramolecular N-H⋯O hydrogen bonds and weak C-H⋯O and Br⋯Br interactions (3.4976(7) Å) were identified.
  • These interactions lead to the formation of specific edge-fused rings (R(2)2(10), R(2)2(15), R(6)6(32)) along the [010] direction.

Conclusions:

  • The crystal structure of nitro-phenyl benzamide is characterized by specific dihedral angles and intramolecular hydrogen bonding.
  • Intermolecular interactions, including halogen bonding, play a significant role in the compound's crystal packing.
  • The observed supramolecular arrangement provides insights into the solid-state behavior of nitro-phenyl benzamide.