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In stereochemistry, an asymmetric carbon is a carbon atom that is bonded to four different types of atoms or groups of atoms. [1] [2] The four atoms and/or groups attached to the carbon atom can be arranged in space in two different ways that are mirror images of each other, and which lead to so-called left-handed and right-handed versions (stereoisomers) of the same molecule.
Chiral molecules will usually have a stereogenic element from which chirality arises. The most common type of stereogenic element is a stereogenic center, or stereocenter. In the case of organic compounds, stereocenters most frequently take the form of a carbon atom with four distinct (different) groups attached to it in a tetrahedral geometry.
A chiral molecule is a type of molecule that has a non-superposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom. [16] [17] The term "chiral" in general is used to describe the object that is non-superposable on its mirror image. [18]
are arranged around the chiral center carbon atom. With the hydrogen atom away from the viewer, if the arrangement of the CO→R→N groups around the carbon atom as center is counter-clockwise, then it is the L form. [14] If the arrangement is clockwise, it is the D form. As usual, if the molecule itself is oriented differently, for example ...
A molecule having exactly one chiral stereocenter (usually an asymmetric carbon atom) can be labeled (R) or (S), but a molecule having multiple stereocenters needs more than one label. For example, the essential amino acid L-threonine contains two chiral stereocenters and is written (2S,3S)-threonine.
Only L configured amino acids are found in biological organisms. All amino acids except for L-cysteine have an S configuration and glycine is non-chiral. [4] In general, all L designated amino acids are enantiomers of their D counterparts except for isoleucine and threonine which contain two carbon stereocenters, making them diastereomers.
The following is a list of straight-chain alkanes, the total number of isomers of each (including branched chains), and their common names, sorted by number of carbon atoms. [ 1 ] [ 2 ] Number of C atoms
For instance, any one pair of CH 2 hydrogens in 3-pentanol (Figure 1) are diastereotopic, as the two CH 2 carbons are enantiotopic. Substitution of any one of the four CH 2 hydrogens creates two chiral centers at once, and the two possible hydrogen substitution products at any one CH 2 carbon will be diastereomers. This kind of relationship is ...