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 (dextrorotatory or dextrorotary — d-rotary, represented by (+), clockwise), or to the left (levorotatory or levorotary — l-rotary, represented by (−), counter-clockwise) depending on which stereoisomer is dominant. For instance, sucrose and camphor are d-rotary whereas cholesterol is l-rotary. For a given substance, the angle by which the polarization of light of a specified wavelength is rotated is proportional to the path length through the material and (for a solution) proportional to its concentration. Optical activity is measured using a polarized source and polarimeter. This is a tool particularly used in the sugar industry to measure the sugar concentration of syrup, and generally in chemistry to measure the concentration or enantiomeric ratio of chiral molecules in solution. Modulation of a liquid crystal's optical activity, viewed between two sheet polarizers, is the principle of operation of liquid-crystal displays (used in most modern televisions and computer monitors).
Forms
Dextrorotation and laevorotation (also spelled levorotation) in chemistry and physics are the optical rotation of plane-polarized light. From the point of view of the observer, dextrorotation refers to clockwise or right-handed rotation, and laevorotation refers to counterclockwise or left-handed rotation. A chemical compound that causes dextrorotation is dextrorotatory or dextrorotary, while a compound that causes laevorotation is laevorotatory or laevorotary. Compounds with these properties consist of chiral molecules and are said to have optical activity. If a chiral molecule is dextrorotary, its enantiomer (geometric mirror image) will be laevorotary, and vice versa. Enantiomers rotate plane-polarized light the same number of degrees, but in opposite directions.
Chirality prefixes
A compound may be labeled as dextrorotary by using the "(+)-" or "d-" prefix. Likewise, a levorotary compound may be labeled using the "(−)-" or "l-" prefix. The International Union of Pure and Applied Chemistry, the authority on chemical nomenclature, strongly discourages use of the "d-" and "l-" prefixes. The lowercase "d-" and "l-" prefixes are distinct from the SMALL CAPS "D-" and "L-" prefixes. The "D-" and "L-" prefixes are used to specify the enantiomer of chiral organic compounds in biochemistry and are based on the compound's absolute configuration relative to (+)-glyceraldehyde, which is the D-form by definition. The prefix used to indicate absolute configuration is not directly related to the (+) or (−) prefix used to indicate optical rotation in the same molecule. For example, nine of the nineteen L-amino acids naturally occurring in proteins are, despite the L- prefix, actually dextrorotary (at a wavelength of 589 nm), and D-fructose is sometimes called "levulose" because it is levorotary. The two naming systems can be combined to indicate both absolute configuration and optical rotation, as in D-(+)-glyceraldehyde. The D- and L- prefixes describe the molecule as a whole, as do the (+) and (−) prefixes for optical rotation. In contrast, the (R)- and (S)- prefixes from the Cahn–Ingold–Prelog priority rules characterize the absolute configuration of each specific chiral stereocenter with the molecule, rather than a property of the molecule as a whole. 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. There is no strict relationship between the R/S, the D/L, and (+)/(−) designations, although some correlations exist. For example, of the naturally occurring amino acids, all are L, and most are (S). For some molecules the (R)-enantiomer is the dextrorotary (+) enantiomer, and in other cases it is the levorotary (−) enantiomer. The relationship must be determined on a case-by-case basis with experimental measurements or detailed computer modeling.
History
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