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Stereochemistry
 
 
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Stereochemistry, a subdiscipline of chemistry
Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
, involves the study of the relative spatial arrangement of atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s within molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
s. An important branch of stereochemistry is the study of chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 molecules .

Stereochemistry is a hugely important facet of chemistry and the study of stereochemical problems spans the entire range of organic
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, inorganic
Inorganic chemistry

Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry....
, biological
Biochemistry

Biochemistry is the study of the chemistry processes in living organisms. It deals with the structure and function of cellular components such as proteins, carbohydrates, lipids, nucleic acids and other biomolecules....
, physical
Physical chemistry

Physical chemistry is the application of physics to macroscopic, microscopic, atomic, subatomic, and particulate phenomena in chemical systems within the field of chemistry traditionally using the principles, practices and concepts of thermodynamics, quantum chemistry, statistical mechanics and kinetics....
 and supramolecular
Supramolecular chemistry

Supramolecular chemistry refers to the area of chemistry beyond the molecules focuses on the chemical systems made up of a discrete number of assembled molecular subunits or components....
 chemistries.

Stereochemistry includes methods for determining and describing these relationships; the effect on the physical
Physics

Physics is the natural science which examines basic concepts such as energy, force, and spacetime and all that derives from these, such as mass, charge, matter and its Motion ....
 or biological
Biology

Biology is a branch of the natural sciences concerned with the study of living organisms and their interaction with each other and their environment ....
 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
Dynamic stereochemistry

In chemistry, dynamic stereochemistry studies the effect of stereochemistry on the reaction rate of a chemical reaction. Stereochemistry is involved in:...
).

Louis Pasteur
Louis Pasteur

Louis Pasteur was a France chemist and microbiologist best known for his remarkable breakthroughs in the causes and prevention of disease. His experiments supported the germ theory of disease, also reducing mortality from puerperal fever , and he created the first vaccine for rabies....
 could rightly be described as the first stereochemist, having observed in 1849 that salt
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
s of tartaric acid
Tartaric acid

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine....
 collected from wine
Wine

Wine is an alcoholic beverage often made of fermentation grape juice. The natural chemical balance of grapes is such that they can ferment without the addition of sugars, acids, enzymes or other nutrients....
 production vessels could rotate plane polarized light, but that salts from other sources did not.






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Isomerism
Stereochemistry, a subdiscipline of chemistry
Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
, involves the study of the relative spatial arrangement of atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
s within molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
s. An important branch of stereochemistry is the study of chiral
Chirality (chemistry)

The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
 molecules .

Stereochemistry is a hugely important facet of chemistry and the study of stereochemical problems spans the entire range of organic
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, inorganic
Inorganic chemistry

Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry....
, biological
Biochemistry

Biochemistry is the study of the chemistry processes in living organisms. It deals with the structure and function of cellular components such as proteins, carbohydrates, lipids, nucleic acids and other biomolecules....
, physical
Physical chemistry

Physical chemistry is the application of physics to macroscopic, microscopic, atomic, subatomic, and particulate phenomena in chemical systems within the field of chemistry traditionally using the principles, practices and concepts of thermodynamics, quantum chemistry, statistical mechanics and kinetics....
 and supramolecular
Supramolecular chemistry

Supramolecular chemistry refers to the area of chemistry beyond the molecules focuses on the chemical systems made up of a discrete number of assembled molecular subunits or components....
 chemistries.

Stereochemistry includes methods for determining and describing these relationships; the effect on the physical
Physics

Physics is the natural science which examines basic concepts such as energy, force, and spacetime and all that derives from these, such as mass, charge, matter and its Motion ....
 or biological
Biology

Biology is a branch of the natural sciences concerned with the study of living organisms and their interaction with each other and their environment ....
 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
Dynamic stereochemistry

In chemistry, dynamic stereochemistry studies the effect of stereochemistry on the reaction rate of a chemical reaction. Stereochemistry is involved in:...
).

Louis Pasteur
Louis Pasteur

Louis Pasteur was a France chemist and microbiologist best known for his remarkable breakthroughs in the causes and prevention of disease. His experiments supported the germ theory of disease, also reducing mortality from puerperal fever , and he created the first vaccine for rabies....
 could rightly be described as the first stereochemist, having observed in 1849 that salt
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
s of tartaric acid
Tartaric acid

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine....
 collected from wine
Wine

Wine is an alcoholic beverage often made of fermentation grape juice. The natural chemical balance of grapes is such that they can ferment without the addition of sugars, acids, enzymes or other nutrients....
 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
Jacobus Henricus van 't Hoff

Jacobus Henricus van 't Hoff was a Netherlands physical chemistry and organic chemistry and the winner of the inaugural Nobel Prize in chemistry....
 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
Thalidomide

Thalidomide is a sedative-hypnotic, and multiple myeloma medication. The drug is a potent Teratology in rabbits and primates including humans: this means that severe birth defects may result if the drug is taken during pregnancy....
 disaster. Thalidomide is a drug
Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
, first prepared in 1957 in Germany
Germany

Germany , officially the Federal Republic of Germany , is a country in Central Europe. It is bordered to the north by the North Sea, Denmark, and the Baltic Sea; to the east by Poland and the Czech Republic; to the south by Austria and Switzerland; and to the west by France, Luxembourg, Belgium, and the Netherlands....
, prescribed for treating morning sickness in pregnant
Pregnancy

Pregnancy is the carrying of one or more offspring, known as a fetus or embryo, inside the uterus of a female. In a pregnancy, there can be multiple gestations, as in the case of twins or Multiple birth....
 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
Genetics

Genetics , a discipline of biology, is the science of heredity and Genetic variation in living organisms. The fact that living things inherit traits from their parents has been used since prehistoric times to improve crop plants and animals through selective breeding....
 damage to early embryonic
Embryo

An embryo is a multicellular organism ploidy eukaryote in its earliest stage of development, from the time of first cell division until birth, Egg , or germination....
 growth and development. In the human body, thalidomide undergoes racemization
Racemization

In chemistry racemization refers to partial conversion of one enantiomer into another....
: even if only one of the two stereoisomers is ingested, the other one is produced. Thalidomide is currently used as a treatment for leprosy
Leprosy

Leprosy , or Hansen's disease , is a Chronic disease caused by the bacteria Mycobacterium leprae and Mycobacterium lepromatosis. Leprosy is primarily a granulomatous disease of the Peripheral nervous system and Mucous membrane of the upper respiratory tract; skin lesions are the primary external symptom....
 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
Fischer projection

The Fischer projection, devised by Hermann Emil Fischer in 1891, is a two-dimensional representation of a Three-dimensional space organic molecule by projection....
 is a simplified way to depict the stereochemistry around a stereocenter.

Types of stereoisomerism
Stereoisomerism

Stereoisomers are isomer that have the same molecular formula and sequence of bonded atoms , but which differ in the three dimensional orientations of their atoms in space....
 are:
  • Atropisomerism
  • Cis-trans isomerism
  • Conformational isomerism
    Conformational isomerism

    In chemistry, conformational isomerism is a form of stereoisomerism in which molecules with the same structural formula exist as different conformational isomers or conformers in 3-D due to rotations about one or more sigma bond....
  • Diastereomers
  • Enantiomers
  • Rotamers


See also

  • Chirality (chemistry)
    Chirality (chemistry)

    The term chiral is used to describe an object that is non-Superposition on its mirror image.Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands...
  • Stereocenter
    Stereocenter

    A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
  • Dynamic stereochemistry
    Dynamic stereochemistry

    In chemistry, dynamic stereochemistry studies the effect of stereochemistry on the reaction rate of a chemical reaction. Stereochemistry is involved in:...
  • Topicity
    Topicity

    In chemistry, topicity is the stereochemical relationship of substituents relative to the structure to which they are attached. Depending on the relationship, such groups can be homotopic, enantiotopic, or diastereotopic....


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