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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
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.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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, or cyano...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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2-(2-Hydroxy-benzyl-ideneamino)benzonitrile.

Rong Xia1, Hai-Jun Xu, Xing-Xuan Gong

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

This study reveals the trans configuration of a C14H10N2O molecule. A strong intramolecular hydrogen bond induces a nearly planar structure, influencing its molecular conformation.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Understanding molecular geometry and conformation is crucial in chemistry.
  • Intramolecular interactions significantly influence the three-dimensional structure of organic molecules.

Purpose of the Study:

  • To determine the precise molecular structure and conformation of the title compound, C14H10N2O.
  • To investigate the role of intramolecular hydrogen bonding in stabilizing the observed molecular geometry.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to elucidate the molecular structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular conformation.

Main Results:

  • The molecule C14H10N2O adopts a trans configuration around the C=N double bond.
  • A strong intramolecular O-H⋯N hydrogen bond was identified, forming a pseudo-ring.
  • The dihedral angle between the two aromatic rings is a notably small 9.3(3)°, indicating a near-planar overall structure.

Conclusions:

  • The observed near-planar conformation of C14H10N2O is primarily driven by a stabilizing intramolecular O-H⋯N hydrogen bond.
  • This finding highlights the significant impact of specific non-covalent interactions on molecular architecture in organic compounds.