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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

13.1K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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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,...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.2K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Synthesis of C62N Containing a Heptagon.

Yoshifumi Hashikawa1, Sheng Zhang1, Yasujiro Murata1

  • 1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.

Organic Letters
|July 25, 2025
PubMed
Summary

Researchers synthesized a novel nitrogen-doped fullerene, C62N, from buckminsterfullerene (C60). This nonclassical fullerene features an N-containing heptagon and exhibits a larger major axis than C60.

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Area of Science:

  • Fullerene science
  • Organic chemistry
  • Materials science

Background:

  • Chemical synthesis of nonclassical fullerenes remains a significant challenge.
  • Previous work included limited examples like C60 conversion to C62 and synthesis of C64N, C65N, and C75N.

Purpose of the Study:

  • To showcase the synthesis of a new nitrogen-doped fullerene, C62N, from C60.
  • To characterize the structure, reactivity, and electronic properties of C62N.

Main Methods:

  • A three-step chemical synthesis route starting from C60.
  • Crystal structure analysis to determine the fullerene's atomic arrangement.
  • Measurement of the fullerene's major axis and comparison with C60.

Main Results:

  • Successful synthesis of C62N from C60.
  • Crystal structure reveals an N-containing heptagon (2,7-dihydro-1H-azepine) on the fullerene sphere.
  • The major axis of C62N is 8.735(5) Å, 23% larger than that of C60.

Conclusions:

  • The study presents a viable method for synthesizing the nonclassical fullerene C62N.
  • The unique N-containing heptagon structure influences the fullerene's properties.
  • Further investigation into the reactivity and electronic properties of C62N is warranted.