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Related Concept Videos

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.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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 constants depend...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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4-Ammonio-benzamidinium dichloride.

Y M Legrand1, A van der Lee, M Barboiu

  • 1Institut Européen des Membranes, UMR 5635, CC 047 Université de Montpellier II, Montpellier, France.

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

The crystal structure of a benzamidine derivative was determined, revealing its capacity for strong hydrogen bonding. This finding is crucial for its application in enzyme purification using affinity chromatography.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Biochemistry

Background:

  • Benzamidine derivatives are vital ligands in affinity chromatography for enzyme purification.
  • Understanding their crystal structure elucidates their hydrogen bonding capabilities in aqueous environments.

Purpose of the Study:

  • To determine the crystal structure of C(7)H(11)N(3)·2Cl(-).
  • To investigate the hydrogen bonding interactions within the crystal lattice.
  • To assess the role of the benzamidine system in forming strong hydrogen bonds.

Main Methods:

  • Single crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of bond lengths, angles, and torsion angles.
  • Identification of hydrogen bonding networks and π-stacking interactions.

Main Results:

  • The crystal structure revealed a twofold rotation axis within the cation.
  • A specific N-C-C-C torsion angle of 40.2° indicates the orientation of the amidinium group.
  • Chloride anions form tetrahedral coordination with four ammonium cations via hydrogen bonds.
  • Aromatic rings exhibit π-stacking with a centroid-centroid distance of 4.178 Å.

Conclusions:

  • The crystal structure confirms the ability of the benzamidine system to form robust hydrogen bonds.
  • The observed interactions support its utility as a ligand in biochemical applications like affinity chromatography.
  • The findings provide a structural basis for the design of related compounds for biomolecule purification.