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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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2-Chloro-5-(chloro-meth-yl)pyridine.

Zhi-Qiang Feng1, Xiao-Li Yang, Yuan-Feng Ye

  • 1School of Material Engineering, Jinling Institute of Technology, Nanjing 211169, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
PubMed
Summary

This study details the near-planar structure of a dichloromethyl compound, C(6)H(5)Cl(2)N. Molecular analysis reveals intermolecular hydrogen bonds forming dimers in the crystal structure.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • The specific compound C(6)H(5)Cl(2)N, a derivative of benzene with dichloromethyl substitution, has not been extensively characterized structurally.
  • Intermolecular interactions, such as hydrogen bonding, play a significant role in the solid-state packing and properties of organic compounds.

Purpose of the Study:

  • To elucidate the precise molecular geometry of the title compound, C(6)H(5)Cl(2)N.
  • To investigate the crystal packing and identify intermolecular interactions present in the solid state.
  • To provide foundational structural data for this dichloromethyl-substituted aromatic compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
  • Analysis of atomic coordinates and bond parameters to assess molecular planarity and deviations.
  • Identification and analysis of intermolecular interactions, specifically hydrogen bonds, within the crystal lattice.

Main Results:

  • The molecule exhibits near-planarity, with root-mean-square (r.m.s.) deviation of 0.0146 Å for most atoms.
  • The chlorine atom of the chloromethyl group is significantly offset from the molecular plane, with a Cl-C-C angle of 111.11(17)°.
  • In the crystal, molecules self-assemble into dimers through intermolecular C-H⋯N hydrogen bonds.

Conclusions:

  • The structural analysis confirms a near-planar conformation for the C(6)H(5)Cl(2)N molecule, with a notable deviation caused by the chloromethyl substituent.
  • The formation of dimers via C-H⋯N hydrogen bonding is a key feature of the crystal structure, influencing molecular assembly.
  • This study provides essential crystallographic data for C(6)H(5)Cl(2)N, contributing to the understanding of halogenated aromatic compounds.