The branch of chemistry that deals with spatial arrangements of atoms in molecules and the effects of these arrangements on the chemical and physical properties of substances.
stereochemical ster'e·o·chem'i·cal (-ĭ-kəl) adj.
stereochemistry
Dictionary:
ster·e·o·chem·is·try (stĕr'ē-ō-kĕm'ĭ-strē, stîr'-)  |
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The study of the three-dimensional arrangement of atoms or groups within molecules and the properties which follow from such arrangement. Molecules that have identical molecular structures but differ in the relative spatial arrangement of component parts are stereoisomers. Inorganic and organic compounds exhibit stereoisomerism. Examples are structures (1)–(8).
The nature of the stereochemistry of a molecule is determined by its symmetry. The symmetry elements to be considered are: planes of symmetry, axes of symmetry, centers of symmetry, and reflection or mirror symmetry. Two types of stereoisomers are known. Those such as (7) and (8), which are devoid of reflection symmetry—which cannot be superimposed on their image in a mirror—are called enantiomers. All other stereoisomers, such as the pairs (1)–(2), (3)–(4), and (5)–(6), are called diastereomers. The configuration of a stereoisomer designates the relative position of the atoms associated with a specific structure. The structures of stereoisomers (1) and (2) differ only in configuration. The same is true for (3) and (4), (5) and (6), and (7) and (8).
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For more information on stereochemistry, visit Britannica.com.
| Columbia Encyclopedia: stereochemistry |
stereochemistry, study of the three-dimensional configuration of the atoms that make up a molecule and the ways in which this arrangement affects the physical and chemical properties of the molecule. It is a third aspect of chemical analysis, the first being the determination of which atoms are present in a molecule and the second being the determination of the interconnections between those atoms by chemical bonds. Central to stereochemistry is the concept of isomerism. Isomers are sets of chemical compounds having identical atomic composition but different structural properties. With geometric isomers, the differences arise from the atoms being bonded in different sequences or patterns. An example is ortho- and para-chlorobenzene; the former has chlorine atoms replacing adjacent carbon atoms in a benzene ring while the latter has chlorine atoms replacing opposing carbon atoms. Optical isomers are pairs of molecules that differ in the same way that a lefthand and righthand screw differ; i.e., they are mirror images of each other. Such molecules with a “handedness” typically rotate the plane of polarization of light that passes through them, but in opposite directions. The sugars glucose and dextrose are a pair of optical isomers; glucose rotates the plane of polarization to the left and dextrose to the right. Stereochemistry is particularly important in biochemistry and molecular biology.
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The branch of chemistry treating of the space relations of atoms in molecules.
| Wikipedia: Stereochemistry |
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules [1].
Stereochemistry is a hugely important facet of chemistry and the study of stereochemical problems spans the entire range of organic, inorganic, biological, physical and supramolecular chemistries.
Stereochemistry includes methods for determining and describing these relationships; the effect on the physical or biological properties these relationships impart upon the molecules in question, and the manner in which these relationships influence the reactivity of the molecules in question (dynamic stereochemistry).
Louis Pasteur could rightly be described as the first stereochemist, having observed in 1849 that salts of tartaric acid collected from wine production vessels could rotate plane polarized light, but that salts from other sources did not. This property, the only physical property in which the two types of tartrate salts differed, is due to optical isomerism. In 1874, Jacobus Henricus van 't Hoff and Joseph Le Bel explained optical activity in terms of the tetrahedral arrangement of the atoms bound to carbon.
One of the most infamous demonstrations of the significance of stereochemistry was the thalidomide disaster. Thalidomide is a drug, first prepared in 1957 in Germany, prescribed for treating morning sickness in pregnant women. The drug however was discovered to cause deformation in babies. It was discovered that one optical isomer of the drug was safe while the other had teratogenic effects, causing serious genetic damage to early embryonic growth and development. In the human body, thalidomide undergoes racemization: even if only one of the two stereoisomers is ingested, the other one is produced. Thalidomide is currently used as a treatment for leprosy and must be used with contraceptives in women to prevent pregnancy-related deformations. This disaster was a driving force behind requiring strict testing of drugs before making them available to the public.
Cahn-Ingold-Prelog priority rules are part of a system for describing a molecule's stereochemistry. They rank the atoms around a stereocenter in a standard way, allowing the relative position of these atoms in the molecule to be described unambiguously. A Fischer projection is a simplified way to depict the stereochemistry around a stereocenter.
Types of stereoisomerism are:
See also
External links
- Information on Thalidomide
- Polarized photomicrographs of crystalline chemicals with descriptions and uses, including tartaric acid
References
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Sci-Tech Encyclopedia. McGraw-Hill Encyclopedia of Science and Technology. Copyright © 2005 by The McGraw-Hill Companies, Inc. All rights reserved. Read more |
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Mentioned in
- absolute configuration (organic chemistry)
- antarafacial (organic chemistry)
- suprafacial (organic chemistry)
- Woodward-Hoffmann rule (organic chemistry)
- van't Hoff, Jacobus Hendricus (Dutch chemist)
- anti (organic chemistry)
- syn (organic chemistry)
- neighbouring-group participation
- Viktor Meyer
- Joseph Achille Le Bel (French chemist)
- alanine (in chemistry)
- Steric effect (chemistry)
- Jacobus Henrikus van'tHoff
- Elias James Corey (American chemist & educator)
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