Enantiomeric Ratio
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Enantiomeric Ratio
In stereochemistry, enantiomeric excess (ee) is a measurement of purity used for chiral substances. It reflects the degree to which a sample contains one enantiomer in greater amounts than the other. A racemic mixture has an ee of 0%, while a single completely pure enantiomer has an ee of 100%. A sample with 70% of one enantiomer and 30% of the other has an ee of 40% (70% − 30%). Definition Enantiomeric excess is defined as the absolute difference between the mole fraction of each enantiomer: :\ ee = , F_R - F_S, where :\ F_R + F_S = 1 In practice, it is most often expressed as a percent enantiomeric excess. The enantiomeric excess can be determined in another way if we know the amount of each enantiomer produced. If one knows the moles of each enantiomer produced then: Enantiomeric excess is used as one of the indicators of the success of an asymmetric synthesis. For mixtures of diastereomers, there are analogous definitions and uses for diastereomeric excess a ...
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Stereochemistry
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which by definition have the same molecular formula and sequence of bonded atoms (constitution), but differ in structural formula (the three-dimensional orientations of their atoms in space). For this reason, it is also known as 3D chemistry—the prefix "stereo-" means "three-dimensionality". Stereochemistry spans the entire spectrum of organic, inorganic, biological, physical and especially supramolecular chemistry. 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 stereochemis ...
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Chemical Purity
In chemistry, chemical purity is the measurement of the amount of impurities found in a sample. Several grades of purity are used by the scientific, pharmaceutical, and industrial communities. Some of the commonly used grades of purity include: * ACS grade is the highest level of purity, and meets the standards set by the American Chemical Society (ACS). The official descriptions of the ACS levels of purity is documented in the ''Reagent Chemicals'' publication, issued by the ACS. It is suitable for food and laboratory uses. * Reagent grade is almost as stringent as the ACS grade. * USP grade meets the purity levels set by the United States Pharmacopeia (USP). USP grade is equivalent to the ACS grade for many drugs. * NF grade is a purity grade set by the National Formulary (NF). NF grade is equivalent to the ACS grade for many drugs. * British Pharmacopoeia: Meets or exceeds requirements set by the British Pharmacopoeia (BP). Can be used for food, drug, and medical purpose ...
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Chiral
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from its mirror image; that is, it cannot be superimposed onto it. Conversely, a mirror image of an ''achiral'' object, such as a sphere, cannot be distinguished from the object. A chiral object and its mirror image are called ''enantiomorphs'' (Greek, "opposite forms") or, when referring to molecules, '' enantiomers''. A non-chiral object is called ''achiral'' (sometimes also ''amphichiral'') and can be superposed on its mirror image. The term was first used by Lord Kelvin in 1893 in the second Robert Boyle Lecture at the Oxford University Junior Scientific Club which was published in 1894: Human hands are perhaps the most recognized example of chirality. The left hand is a non-superimposable mirror image of the right hand; no matter ho ...
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Enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are non-superposable onto their own mirror image. Enantiomers are much like one's right and left hands, when looking at the same face, they cannot be superposed onto each other. No amount of reorientation will allow the four unique groups on the chiral carbon (see Chirality (chemistry)) to line up exactly. The number of stereoisomers a molecule has can be determined by the number of chiral carbons it has. Stereoisomers include both enantiomers and diastereomers. Diastereomers, like enantiomers, share the same molecular formula and are non-superposable onto each other however, they are not mirror images of each other. A molecule with chirality rotates plane-polarized light. A mixture of equals a ...
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Racemic
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. History The first known racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid. He manually separated the crystals of a mixture by hand, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt that gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from the macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an ''enantiomerically pure'' or ''enantiopure'' compound. Etymology From racemic acid found in grapes; from Latin ''racemus'', meani ...
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Absolute Difference
The absolute difference of two real numbers x and y is given by , x-y, , the absolute value of their difference. It describes the distance on the real line between the points corresponding to x and y. It is a special case of the Lp distance for all 1\le p\le\infty and is the standard metric used for both the set of rational numbers \Q and their completion, the set of real numbers \R. As with any metric, the metric properties hold: * , x-y, \ge 0, since absolute value is always non-negative. * , x-y, = 0   if and only if   x=y. * , x-y, =, y-x,     (''symmetry'' or ''commutativity''). * , x-z, \le, x-y, +, y-z,     (''triangle inequality''); in the case of the absolute difference, equality holds if and only if x\le y\le z or x\ge y\ge z. By contrast, simple subtraction is not non-negative or commutative, but it does obey the second and fourth properties above, since x-y=0 if and only if x=y, and x-z=(x-y)+(y-z). The absolute difference ...
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Mole Fraction
In chemistry, the mole fraction or molar fraction (''xi'' or ) is defined as unit of the amount of a constituent (expressed in moles), ''ni'', divided by the total amount of all constituents in a mixture (also expressed in moles), ''n''tot. This expression is given below: :x_i = \frac The sum of all the mole fractions is equal to 1: :\sum_^ n_i = n_\mathrm ; \ \sum_^ x_i = 1. The same concept expressed with a denominator of 100 is the mole percent, molar percentage or molar proportion (mol%). The mole fraction is also called the amount fraction. It is identical to the number fraction, which is defined as the number of molecules of a constituent ''Ni'' divided by the total number of all molecules ''N''tot. The mole fraction is sometimes denoted by the lowercase Greek letter (chi) instead of a Roman ''x''. For mixtures of gases, IUPAC recommends the letter ''y''. The National Institute of Standards and Technology of the United States prefers the term amount-of-substance fraction o ...
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Asymmetric Synthesis
Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers. Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity. Overview Many of the building blocks of biological systems such as sugars and amino acids are produced exclusively as ...
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Diastereomer
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus typically increases the number of stereoisomers by a factor of two. Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers that differ in all stereocenters and are therefore mirror images of one another. Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding the opposing enantiomer). Diastereomers h ...
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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 materials. Circular birefringence and circular dichroism are the manifestations of optical activity. Optical activity occurs only in chiral materials, those lacking microscopic mirror symmetry. Unlike other sources of birefringence which alter a beam's state of polarization, optical activity can be observed in fluids. This can include gases or solutions of chiral molecules such as sugars, molecules with helical secondary structure such as some proteins, and also chiral liquid crystals. It can also be observed in chiral solids such as certain crystals with a rotation between adjacent crystal planes (such as quartz) or metamaterials. When looking at the source of light, the rotation of the plane of polarization may be either to the right (dextrorotator ...
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Specific Rotation
In chemistry, specific rotation ( '') is a property of a chiral chemical compound. It is defined as the change in orientation of monochromatic plane-polarized light, per unit distance–concentration product, as the light passes through a sample of a compound in solution. Compounds which rotate the plane of polarization of a beam of plane polarized light clockwise are said to be dextrorotary, and correspond with positive specific rotation values, while compounds which rotate the plane of polarization of plane polarized light counterclockwise are said to be levorotary, and correspond with negative values. If a compound is able to rotate the plane of polarization of plane-polarized light, it is said to be “ optically active”. Specific rotation is an intensive property, distinguishing it from the more general phenomenon of optical rotation. As such, the ''observed'' rotation (α) of a sample of a compound can be used to quantify the enantiomeric excess of that compound, provid ...
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Chiral Column Chromatography
Chiral column chromatography is a variant of column chromatography that is employed for the separation of enantiomers, e. g. in racemates. The stationary phase contains a single enantiomer of a chiral compound. The chiral stationary phase can be prepared by attaching a chiral compound to the surface of an achiral support such as silica gel. Common chiral stationary phases are based on oligosaccharides such as cellulose or cyclodextrin (in particular with β-cyclodextrin, a seven sugar ring molecule). The principle can be also applied to the fabrication of monolithic HPLC columns or gas chromatography Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for separating and analyzing compounds that can be vaporized without decomposition. Typical uses of GC include testing the purity of a particular substance, ... columns. References Chromatography Stereochemistry {{chemistry-stub ...
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