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Related Concept Videos

Chirality02:25

Chirality

31.0K
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.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
31.0K
Prochirality02:05

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 in Nature02:30

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
17.5K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

15.9K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
15.9K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.2K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.2K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

11.6K
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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Updated: Mar 7, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Chirality in curved polyaromatic systems.

Michel Rickhaus1, Marcel Mayor2, Michal Juríček3

  • 1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland. marcel.mayor@unibas.ch and Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, OX1 3TA Oxford, UK.

Chemical Society Reviews
|February 23, 2017
PubMed
Summary
This summary is machine-generated.

This review categorizes chiral molecular fragments of non-planar carbon allotropes, including hypothetical forms. Understanding their symmetry and dynamics is key for designing new chiral carbon materials.

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Area of Science:

  • Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Carbon allotropes (e.g., graphene, carbon nanotubes, fullerenes) exhibit unique properties due to their delocalized π-conjugated electronic structure.
  • Non-planar sp2-hybridized carbon structures possess bent or curved geometries, leading to diverse physical and chemical characteristics.

Purpose of the Study:

  • To conceptually categorize chiral synthetic molecular fragments of non-planar sp2-carbon allotropes.
  • To analyze bent (zero Gaussian curvature) and curved (positive/negative Gaussian curvature) molecular systems.
  • To provide guidelines for designing molecular fragments that encode chirality.

Main Methods:

  • Conceptual analysis and categorization of molecular systems based on geometry and symmetry.
  • Examination of two types of molecular systems: bent and curved.
  • Application of chirality criteria: absence of inversion center and mirror plane, and stereochemical rigidity.

Main Results:

  • Identification of two classes of molecular systems: bent (zero Gaussian curvature) and curved (positive/negative Gaussian curvature).
  • Emphasis on the necessity of considering both symmetry and structural dynamics for chirality.
  • Development of principles for designing chiral molecular fragments.

Conclusions:

  • Chirality in non-planar carbon allotropes depends on the absence of specific symmetry elements and stereochemical rigidity.
  • The study provides a framework for understanding and designing chiral carbon-based molecular fragments.
  • These principles can guide the creation of larger chiral systems with tailored properties.