Organic Chemistry And Reaction Mechanisms Codexery

Chirality (chemistry)

Geometric property where a molecule cannot be superposed on its mirror image.

Last updated

Chirality (chemistry)

Wikimedia Commons · Public domain

A molecule or ion is chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes.[1] The geometric property of chirality gets its name from the Ancient Greek word for 'hand', a classic example of an object that cannot be superimposed on its mirror image.[1]

Quick Facts

Field
Chemistry
Subfield
Stereochemistry
Key concept
Chirality
Origin term
Ancient Greek χείρ (cheir) 'hand'
Common example
Hand (canonical object with chirality)
Related terms
  • Enantiomers
  • racemic mixture
  • stereocenter

Facts from the source article.

Key facts and history

Alfred Werner resolved a purely inorganic cobalt complex called hexol in 1911, overthrowing the misconception that chirality was restricted to organic chemistry.[2] Spearmint leaves contain the R-(−)-carvone enantiomer, while caraway seeds contain the S-(+)-carvone enantiomer, and the two smell different to most people because our olfactory receptors are chiral.[3] In 1812, Jean-Baptiste Biot was the first person to observe that chiral substances rotate plane polarized light.[4] By 1848, Louis Pasteur had concluded that the optical activity he observed originated at the molecular level.[2]

Lord Kelvin first introduced the word "chirality" in 1894.[2] Research conducted in the early 1970s by several independent groups demonstrated that humans can smell the difference between chiral compounds.[5] Chirality is a widespread and practically significant phenomenon within both coordination chemistry and organometallic chemistry.[6]

What the research sources say

SMILES uses a local chirality representation, as opposed to absolute chirality, which allows partial specifications.[7] Neural network architectures, particularly Transformers, face inherent challenges in learning stereochemical features from string-based representations like SMILES.[8] These models tend to recognize partial molecular structures early in training but require significantly longer to accurately distinguish between enantiomers.[8] Predictive models for specific rotation values of chiral molecules have been built, with applications extending to both general organic compounds and specialized groups like chiral fluorinated molecules.[9]

References

  1. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Organic Chemistry (4th Edition) Paula Y. Bruice. Pearson Educational Books.; Organic Chemistry (3rd Edition) Marye Anne Fox, James K. Whitesell Jones & Bartlett Publishers (2004); ; (original not read by us) en.wikipedia.org
  2. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Pasteur, L., "Researches on the molecular asymmetry of natural organic products, English translation of French original, published by Alembic Club Reprints (Vol. 14, pp. 1–46) in 1905, facsimile reproduction by SPIE in a; "Stereochemistry of Organic Compounds", Wiley & Sons, 1994; Bentley, Ronald, "From Optical Activity in Quartz to Chiral Drugs: Molecular Handedness in Biology and Medicine.", Perspect. Biol. Med., 1995, p. 188–229; ; Werner, "Zur Kenntnis des asymmetrischen Kobaltatoms. I", Berichte der Deutschen Chemischen Gesel en.wikipedia.org
  3. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Meierhenrich, Uwe J., "Amino acids and the Asymmetry of Life", Springer, 2008; "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones", J. Agric. Food Chem., 1971, p. 785–787 (we also read that source) en.wikipedia.org
  4. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Frankel, "Corpuscular Optics and the Wave Theory of Light: The Science and Politics of a Revolution in Physics", Social Studies of Science, 1976, p. 147–154 (original not read by us) en.wikipedia.org
  5. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones", J. Agric. Food Chem., 1971, p. 785–787; Friedman, "Odor Incongruity and Chirality", Science, 1971, p. 1044–1046; Ohloff, "Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances", Helvetica Chimica Acta, 1980, p. 1932–1946 (original not read by us) en.wikipedia.org
  6. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: von Zelewsky, A. (1995). Stereochemistry of Coordination Compounds. Chichester: John Wiley.. . (original not read by us) en.wikipedia.org
  7. "Daylight Theory: SMILES", www.daylight.com. facts only, no text reused. daylight.com
  8. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Yoshikai, "Difficulty in chirality recognition for Transformer architectures learning chemical structures from string representations", Nature Communications, 2024-02-16, p. 1197 (we also read that source) en.wikipedia.org
  9. Wikipedia, "Chirality (chemistry)" (CC BY-SA 4.0), which cites: Chen, "Machine learning to predict the specific optical rotations of chiral fluorinated molecules", Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019-12-05; Mamede, "Machine Learning Classification of One-Chiral-Center Organic Molecules According to Optical Rotation", Journal of Chemical Information and Modeling, 2021-01-25, p. 67–75 (we also read that source) en.wikipedia.org

Each numbered sentence above was checked against the source it cites before publication. Sentences citing Wikipedia adapt text from the English Wikipedia article Chirality (chemistry) (contributors), used under CC BY-SA 4.0; this entry is available under the same licence. Other sources were used for facts only; no text or images are copied from them.

More in Organic Chemistry And Reaction Mechanisms

Cis–trans isomerismConvergent synthesisCycloadditionDiels–Alder reactionDiastereomerDivergent synthesisE1cB-elimination reactionEi mechanismElectrophilic additionElectrophilic substitutionElimination reactionEnantiomer

Sources

Compiled from Wikipedia and the sources listed below. Text from Wikipedia is available under CC BY-SA 4.0; this entry is adapted from it.

Spotted an error? Know more?

Reader corrections go straight into our review queue. Suggest an edit · How this site is sourced

Comments

Loading…
Open in the interactive codex →