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Asymmetric Carbon
An asymmetric carbon atom (chiral carbon) is a carbon atom that is attached to four different types of atoms or groups of atoms. Le Bel-van't Hoff rule states that the number of stereoisomers of an organic compound is 2n, where n represents the number of asymmetric carbon atoms (unless there is an internal plane of symmetry); a corollary of Le Bel and van't Hoff's simultaneously announced conclusions, in 1874, that the most probable orientation of the bonds of a carbon atom linked to four groups or atoms is toward the apexes of a tetrahedron, and that this accounted for all then-known phenomena of molecular asymmetry (which involved a carbon atom bearing four different atoms or groups). Knowing the number of asymmetric carbon atoms, one can calculate the maximum possible number of stereoisomers for any given molecule as follows: : If n is the number of asymmetric carbon atoms then the maximum number of isomers = 2n ( Le Bel-van't Hoff rule) As an example, malic acid has 4 carb ...
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Carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Description The combining capacity, or affinity of an ...—its atom making four electrons available to form covalent bond, covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three Isotopes of carbon, isotopes occur naturally, Carbon-12, C and Carbon-13, C being stable, while Carbon-14, C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the Timeline of chemical element discoveries#Ancient discoveries, few elements known since antiquity. Carbon is the 15th Abundance of elements in Earth's crust, most abundant element in the Earth's crust, and the Abundance of the c ...
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Atom
Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, and plasma is composed of neutral or ionized atoms. Atoms are extremely small, typically around 100 picometers across. They are so small that accurately predicting their behavior using classical physics, as if they were tennis balls for example, is not possible due to quantum effects. More than 99.94% of an atom's mass is in the nucleus. The protons have a positive electric charge, the electrons have a negative electric charge, and the neutrons have no electric charge. If the number of protons and electrons are equal, then the atom is electrically neutral. If an atom has more or fewer electrons than protons, then it has an overall negative or positive charge, respectively – such atoms are called ions. The electrons of an atom are a ...
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Joseph Achille Le Bel
Joseph Achille Le Bel (21 January 1847 in Pechelbronn – 6 August 1930, in Paris, France) was a French chemist. He is best known for his work in stereochemistry. Le Bel was educated at the École Polytechnique in Paris. In 1874 he announced his theory outlining the relationship between molecular structure and optical activity. This discovery laid the foundation of the science of stereochemistry, which deals with the spatial arrangement of atoms in molecules. This hypothesis was put forward in the same year by the Dutch physical chemist Jacobus Henricus van 't Hoff and is currently known as Le Bel–van't Hoff rule. Le Bel wrote ''Cosmologie Rationelle'' (Rational Cosmology) in 1929. Works * * * See also * Hexamethylbenzene *Optical rotation Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain m ...
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Stereoisomers
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer. Enantiomers Enantiomers, also known as optical isomers, are two stereoisomers that are related to each other by a reflection: they are mirror images of each other that are non-superposable. Human hands are a macroscopic analog of this. Every stereogenic center in one has the opposite configuration in the other. Two compounds that are enantiomers of each other have the same physical properties, except for the direction in which they rotate polarized light and how they interact with different optical is ...
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Malic Acid
Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is an intermediate in the citric acid cycle. Etymology The word 'malic' is derived from Latin ' mālum', meaning 'apple'. The related Latin word , meaning 'apple tree', is used as the name of the genus ''Malus'', which includes all apples and crabapples; and the origin of other taxonomic classifications such as Maloideae, Malinae, and Maleae. Biochemistry L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically. File:L-Äpfelsäure.svg, L-Malic acid File:D-Äpfelsäure.svg, D-Malic acid Malate plays an important role in biochemistry. In the ...
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Tetrose
A tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde functional group in position 1 (aldotetroses) or a ketone functional group in position 2 (ketotetroses). File:DErythrose Fischer.svg , D-Erythrose File:DThreose Fischer.svg , D-Threose File:DErythrulose Fischer.svg , D-Erythrulose The aldotetroses have two chiral centers (asymmetric carbon atoms) and so 4 different stereoisomers are possible. There are two naturally occurring stereoisomers, the enantiomers of erythrose and threose having the D configuration but not the L enantiomers. The ketotetroses have one chiral center and, therefore, two possible stereoisomers: erythrulose (L- and D-form). Again, only the D enantiomer is naturally occurring. Biological Functions There are a few known ways that tetrose sugars are used in nature. Some are seen in metabolic pathways and others are known to affect certain enzymes. Intermediates in the Pentose Phosphate Pathway One of the metabolic pathways tha ...
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Tetrose
A tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde functional group in position 1 (aldotetroses) or a ketone functional group in position 2 (ketotetroses). File:DErythrose Fischer.svg , D-Erythrose File:DThreose Fischer.svg , D-Threose File:DErythrulose Fischer.svg , D-Erythrulose The aldotetroses have two chiral centers (asymmetric carbon atoms) and so 4 different stereoisomers are possible. There are two naturally occurring stereoisomers, the enantiomers of erythrose and threose having the D configuration but not the L enantiomers. The ketotetroses have one chiral center and, therefore, two possible stereoisomers: erythrulose (L- and D-form). Again, only the D enantiomer is naturally occurring. Biological Functions There are a few known ways that tetrose sugars are used in nature. Some are seen in metabolic pathways and others are known to affect certain enzymes. Intermediates in the Pentose Phosphate Pathway One of the metabolic pathways tha ...
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Aldopentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.-Ribose
. PubChem compound webpage, accessed on 2010-02-06.
Pentoses are very important in . is a constituent of , and the related molecule, , is a constituent of
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Aldopentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.-Ribose
. PubChem compound webpage, accessed on 2010-02-06.
Pentoses are very important in . is a constituent of , and the related molecule, , is a constituent of
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