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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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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Chair Conformation of Cyclohexane02:02

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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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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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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Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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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.
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A Co-conformationally "Topologically" Chiral Catenane.

Arnau Rodríguez-Rubio1, Andrea Savoini1, Florian Modicom1

  • 1Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom.

Journal of the American Chemical Society
|June 28, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel catenane with a unique chiral unit. This breakthrough in topological chirality offers new possibilities for designing complex molecular architectures.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Stereochemistry

Background:

  • Topological chirality in catenanes arises from the specific arrangement of atoms within achiral rings, leading to Cnh symmetry.
  • A related but less-explored form of chirality, termed "co-conformationally topologically chiral," occurs when a symmetric ring (Cnv) is influenced by an adjacent oriented macrocycle.

Purpose of the Study:

  • To synthesize a highly enantioenriched catenane featuring the "co-conformationally topologically chiral" stereogenic unit.
  • To explore and demonstrate this overlooked source of chirality in mechanically interlocked molecules.

Main Methods:

  • Synthesis of a novel catenane structure.
  • Utilizing techniques to achieve high enantiomeric enrichment.
  • Characterization of the resulting molecular architecture and its chiral properties.

Main Results:

  • Successful synthesis of a catenane with a highly enantioenriched co-conformationally chiral unit.
  • Demonstration of desymmetrization of a Cnv ring by an oriented macrocycle.
  • Confirmation of the novel stereogenic unit's existence and contribution to overall chirality.

Conclusions:

  • The study presents a new method for creating topologically chiral catenanes.
  • Highlights the significance of co-conformationally chiral units in molecular design.
  • Opens avenues for developing advanced chiral materials and catalysts based on catenanes.