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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).
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Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
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Preparation and Reactions of Sulfides02:26

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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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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1,6-Bis(chloro-meth-yl)pyridine.

Richard Betz1, Thomas Gerber, Henk Schalekamp

  • 1Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|August 13, 2011
PubMed
Summary
This summary is machine-generated.

This study characterizes a halogenated 2,6-lutidine derivative, revealing specific molecular arrangements. The compound forms chains via weak chlorine-to-chlorine contacts and exhibits pi-pi interactions.

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

Published on: April 27, 2017

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • 2,6-Lutidine derivatives are important in organic synthesis.
  • Halogenated organic compounds exhibit unique chemical properties.
  • Understanding intermolecular interactions is key to material science.

Purpose of the Study:

  • To determine the crystal structure of a novel halogenated 2,6-lutidine derivative.
  • To investigate the intermolecular interactions, including halogen bonding and pi-pi stacking.
  • To elucidate the self-assembly behavior of the molecule in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the crystal structure.
  • Analysis of C-Cl bond vectors and distances.
  • Identification and quantification of intermolecular contacts (Cl...Cl and pi-pi interactions).

Main Results:

  • The compound, C(7)H(7)Cl(2)N, features chloro-methyl groups with C-Cl vectors oriented oppositely relative to the aromatic plane.
  • A weak dispersive Cl⋯Cl contact of 3.4342(3) Å links molecules into a chain along the [101] direction.
  • A π-π interaction with a centroid-centroid distance of 3.7481(5) Å was observed, indicating further molecular association.

Conclusions:

  • The crystal structure reveals a specific spatial arrangement of halogen atoms.
  • Intermolecular chlorine-chlorine contacts and pi-pi interactions play a significant role in the compound's solid-state architecture.
  • This study provides insights into the supramolecular chemistry of halogenated pyridines.