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Related Concept Videos

Carbon Skeletons01:12

Carbon Skeletons

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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side...
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Hydrogen Bonds01:04

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Structure of Alkanes02:23

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The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
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Hybridization of Atomic Orbitals II03:35

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sp3d and sp3d 2 Hybridization
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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.
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Oxygen- and Nitrogen-Embedded Zigzag Hydrocarbon Belts.

Mei-Ling Tan1,2, Qing-Hui Guo2, Xue-Yuan Wang2

  • 1Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064, China.

Angewandte Chemie (International Ed. in English)
|October 13, 2020
PubMed
Summary

Researchers synthesized novel O/N-doped zigzag hydrocarbon belts, overcoming synthetic challenges. These unique heteroatom-linked belts exhibit distinct photophysical and redox properties, expanding the scope of complex molecular architectures.

Keywords:
nucleophilic aromatic substitutionoctahydrobelt[8]arenespalladium-catalyzed C−N bond formationstrained macrocycleszigzag hydrocarbon belts

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Zigzag hydrocarbon belts and their heteroatom analogues are desirable targets due to their unique properties.
  • However, their synthesis remains a significant challenge in organic chemistry.

Purpose of the Study:

  • To report the synthesis of diverse O/N-doped zigzag hydrocarbon belts.
  • To explore the construction of heteroatom-linked octahydrobelt[8]arenes.

Main Methods:

  • Utilizing intramolecular SN Ar reactions for selective bridging.
  • Employing palladium-catalyzed intermolecular C-N bond formation.
  • Leveraging preorganized conformations of resorcin[4]arene derivatives to facilitate cyclization.

Main Results:

  • Successfully synthesized diverse O/N-doped zigzag hydrocarbon belts.
  • Obtained strained square-prism-shaped belt structures with unique boat conformations.
  • Demonstrated that heteroatom-bearing belts possess distinct photophysical and redox properties compared to hydrocarbon analogues.

Conclusions:

  • The developed synthetic strategies enable the construction of complex heteroatom-linked belt architectures.
  • The synthesized belts represent a novel class of molecules with tunable properties.
  • This work opens new avenues for designing functional organic materials.