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Related Concept Videos

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.
Removing one hydrogen from the intervening CH2 group with both...
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
IUPAC Nomenclature of Carboxylic Acids01:16

IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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(E)-7-(Pyren-1-yl)hept-6-enoic acid.

Arto Valkonen1, Tanja Lahtinen, Kari Rissanen

  • 1Department of Chemistry, Nanoscience Center, University of Jyväskylä, PO Box 35, FIN-40014 University of Jyväskylä, Finland.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
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This study details a pyrene-based molecule designed for attachment to carbon nanotubes. Its carboxylic acid groups form hydrogen bonds, enabling supramolecular assembly for advanced materials.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Pyrene-based compounds are explored for their unique photophysical properties and potential in materials science.
  • Carbon nanotubes (CNTs) offer exceptional mechanical and electrical properties, driving research into functionalization methods.
  • Supramolecular chemistry provides tools for designing molecular architectures with specific functions, such as non-covalent attachment.

Purpose of the Study:

  • To synthesize and characterize a pyrene-based molecule as a precursor for supramolecular assembly.
  • To investigate the non-covalent attachment of this molecule to carbon nanotubes.
  • To understand the intermolecular interactions governing the crystal structure and self-assembly.

Main Methods:

  • Crystallographic analysis was employed to determine the molecular and crystal structure.
  • Characterization of the compound C(23)H(20)O(2) was performed.
  • Analysis of hydrogen bonding and π-π stacking interactions within the crystal lattice.

Main Results:

  • The crystal structure reveals three independent molecules in the asymmetric unit.
  • Carboxylic acid groups facilitate the formation of a characteristic double O-H⋯O hydrogen-bond motif, creating an eight-membered ring.
  • Weaker interactions, including C-H⋯O, π-π stacking (centroid-centroid distance = 3.968 Å), and C-H⋯π interactions, were identified.

Conclusions:

  • The synthesized pyrene-based compound serves as a viable precursor for supramolecular elements.
  • The observed hydrogen bonding and π-π interactions are crucial for the molecule's self-assembly and potential attachment to carbon nanotubes.
  • This research contributes to the development of novel methods for functionalizing carbon nanotubes for advanced applications.