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Related Concept Videos

Chirality02:25

Chirality

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...
Chirality in Nature02:30

Chirality in Nature

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. The...
Prochirality02:05

Prochirality

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...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

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Chiral: a confusing etymology.

Ronald Bentley1

  • 1Department of Biological Sciences, University of Pittsburgh, Pittsburgh, Pennsylvania, USA. rbentley@pitt.edu

Chirality
|February 21, 2009
PubMed
Summary
This summary is machine-generated.

Lord Kelvin coined "chiral" in the 1890s, but earlier overlooked definitions of "heterochiral" and "homochiral" from 1879 reveal deeper etymological roots. This analysis explores the origin and evolution of chirality terminology.

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Area of Science:

  • Chemistry
  • Physics
  • History of Science

Background:

  • The term "chiral" was formally defined by Lord Kelvin in 1893-1894.
  • Existing literature presents varied dates for the definition of chirality, ranging from 1884 to 1904.
  • Lord Kelvin used "heterochiral" and "homochiral" in 1873, though this note is lost.

Purpose of the Study:

  • To investigate the precise etymological origins of the term "chiral" and related concepts.
  • To highlight previously overlooked definitions of "heterochiral" and "homochiral" by Lord Kelvin.
  • To provide a comprehensive analysis of the historical development of chirality terminology.

Main Methods:

  • Literature review of scientific publications and historical texts.
  • Analysis of Lord Kelvin's published works and coauthored texts.
  • Examination of the etymology of scientific neologisms related to chirality.

Main Results:

  • Lord Kelvin's definitions of "heterochiral" and "homochiral" in an 1879 coauthored text were apparently overlooked.
  • The widely cited date for the definition of "chiral" (1893-1894) may not represent the earliest conceptualization.
  • The etymological roots of chirality extend further back than commonly acknowledged.

Conclusions:

  • The historical understanding and definition of chirality require revision based on overlooked primary sources.
  • Lord Kelvin's early contributions to the terminology of chirality are more extensive than previously recognized.
  • A thorough examination of scientific etymology is crucial for accurate historical context.