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Related Concept Videos

Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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.
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 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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N,N'-bis(2-hydroxycyclohexyl)-N,N'-bis(2-hydroxyethyl)ethane-1,2-diaminium dichloride.

Alvaro S de Sousa1, Zanele Hlam, Manuel A Fernandes

  • 1School of Chemistry, Molecular Sciences Institute, University of the Witwatersrand, Private Bag 3, Wits 2050, Johannesburg, South Africa. alvaro.desousa@wits.ac.za

Acta Crystallographica. Section C, Crystal Structure Communications
|November 6, 2010
PubMed
Summary

This study details the crystal structure of an achiral meso compound, revealing undulating layers formed by chains linked through specific C-H...Cl interactions. These chains exhibit unique hydrogen-bonded dimers and N-alkyl bridges influencing molecular arrangement.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the self-assembly of organic molecules is crucial for designing novel materials.
  • The role of weak interactions, such as C-H...Cl bonds, in crystal engineering is an active area of research.
  • Meso compounds, possessing chiral centers but an overall achiral nature, present unique structural challenges and opportunities.

Purpose of the Study:

  • To elucidate the crystal structure of the achiral meso form of C(18)H(38)N(2)O(4)(2+)·2Cl(-).
  • To investigate the intermolecular interactions governing the self-assembly of this compound in the solid state.
  • To analyze the structural motifs, including hydrogen bonding and hydrophobic/hydrophilic segregation.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
  • Analysis of hydrogen bonding networks, including N-H...Cl and O-H...Cl interactions.
  • Examination of the packing arrangement and the role of alkyl and cycloalkyl groups in structural organization.

Main Results:

  • The achiral meso compound crystallizes into undulating layers composed of molecular chains.
  • Chains are interconnected by weak hydroxyalkyl C-H...Cl contacts.
  • Centrosymmetric hydrogen-bonded dimers, formed by N-H...Cl and O-H...Cl interactions, characterize the chains.
  • Trans-N-alkyl bridges create distinct hydrophilic segments and hydrophobic cycloalkyl stacks along the [001] direction.

Conclusions:

  • The crystal structure reveals a well-defined supramolecular architecture driven by specific hydrogen bonding and van der Waals forces.
  • The arrangement highlights the interplay between hydrophilic and hydrophobic moieties in directing crystal packing.
  • This structural understanding provides insights into the solid-state behavior of meso compounds with potential implications in materials science.