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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

22.6K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
22.6K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.2K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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...
4.3K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
4.3K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

6.1K
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,...
6.1K

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Belt-Shaped Cyclonaphthylenes.

Zhe Sun1, Parantap Sarkar2, Takuya Suenaga2

  • 1JST, ERATO, Isobe Degenerate π-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan).

Angewandte Chemie (International Ed. in English)
|September 3, 2015
PubMed
Summary
This summary is machine-generated.

Researchers created the first belt-shaped cyclonaphthylenes with curved pi systems. These novel macrocycles, derived from naphthalene units, offer potential for new nanomaterial applications.

Keywords:
arenesatropisomerismcycloarylenesmacrocyclesnanotubes

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Cyclo-para-phenylenes demonstrate radial π-systems in nanohoop structures.
  • Macrocycles composed of benzene units are well-established.
  • Naphthalene-based macrocycles (cyclonaphthylenes) are less explored, with no reported radial π-systems.

Purpose of the Study:

  • To synthesize and characterize the first belt-shaped cyclonaphthylenes with curved π-systems.
  • To investigate the structural properties and conformational flexibility of these novel macrocycles.

Main Methods:

  • Synthesis of [8]cyclo-amphi-naphthylene via specific linkage at the 2,6-positions of naphthalene units.
  • Structural analysis in solution and solid-state.
  • Investigation of conformational rigidity using methylene bridges.

Main Results:

  • Successful synthesis of the first belt-shaped cyclonaphthylenes, [8]cyclo-amphi-naphthylene.
  • The synthesized molecules exhibit curved π-systems.
  • Flexible structures in solution allow for naphthalene unit rotation; rigidity achieved with methylene bridges.

Conclusions:

  • This study reports the first example of belt-shaped cyclonaphthylenes, expanding the scope of macrocyclic chemistry.
  • The development of these curved π-systems in naphthalene-based macrocycles opens new avenues for functional nanomaterials.
  • The ability to control molecular rigidity is crucial for designing persistent molecular structures.