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Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. [1] The study of stereochemistry focuses on the relationships between stereoisomers, which are defined as having the same molecular formula and sequence of bonded atoms (constitution) but differing in the geometric positioning of the atoms in space.
Chirality is an important concept for stereochemistry and biochemistry. Most substances relevant to biology are chiral, such as carbohydrates ( sugars , starch , and cellulose ), all but one of the amino acids that are the building blocks of proteins , and the nucleic acids .
In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. [1] [2] The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically ...
In the case of the health condition situs inversus totalis, in which all the internal organs are flipped horizontally (i.e. the heart placed slightly to the right instead of the left), chirality poses some problems should the patient require a liver or heart transplant, as these organs are chiral, thus meaning that the blood vessels which ...
Determining stereochemistry in atropisomers using the helicity rule follows the priority: front substituent A > backward substituent A > front substituent B > backward substituent B Determining the axial stereochemistry of biaryl atropisomers can be accomplished through the use of a Newman projection along the axis of hindered rotation.
The quality of stereospecificity is focused on the reactants and their stereochemistry; it is concerned with the products too, but only as they provide evidence of a difference in behavior between reactants. Of stereoisomeric reactants, each behaves in its own specific way. Stereospecificity towards enantiomers is called enantiospecificity.
The concepts of syn and anti addition are used to characterize the different reactions of organic chemistry by reflecting the stereochemistry of the products in a reaction. The type of addition that occurs depends on multiple different factors of a reaction, and is defined by the final orientation of the substituents on the parent molecule.
Enantiotopic groups are identical and indistinguishable except in chiral environments. For instance, the CH 2 hydrogens in ethanol (CH 3 CH 2 OH) are normally enantiotopic, but can be made different (diastereotopic) if combined with a chiral center, for instance by conversion to an ester of a chiral carboxylic acid such as lactic acid, or if coordinated to a chiral metal center, or if ...