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 stereo ...

, the Klyne–Prelog system (named for

William Klyne William Klyne (March 23, 1913, in Enfield, Middlesex – November 13, 1977) was an organic chemist known for his work in steroids and stereochemistry — a field in which he was a "pioneer", and in which Ernest Eliel and Norman Allinger Nor ...

and

Vladimir Prelog Vladimir Prelog (23 July 1906 – 7 January 1998) was a Croatian-Swiss organic chemist who received the 1975 Nobel Prize in chemistry for his research into the stereochemistry of organic molecules and reactions. Prelog was born and grew up in ...

) for describing conformations about a

single bond In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of ...

offers a more systematic means to unambiguously name complex structures, where the torsional or

dihedral angles A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the un ...

are not found to occur in 60° increments. Klyne notation views the placement of the

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...

on the front atom as being in regions of space called anti/syn and clinal/periplanar relative to a reference group on the rear atom. A plus (+) or minus (–) sign is placed at the front to indicate the sign of the dihedral angle. Anti or syn indicates the substituents are on opposite sides or the same side, respectively. Clinal substituents are found within 30° of either side of a dihedral angle of 60° (from 30° to 90°), 120° (90°–150°), 240° (210°–270°), or 300° (270°–330°). Periplanar substituents are found within 30° of either 0° (330°–30°) or 180° (150°–210°). Juxtaposing the designations produces the following terms for the conformers of

butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name bu ...

(''see

Alkane stereochemistry In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a mol ...

for an explanation of conformation nomenclature''):

gauche Gauche may refer to: * Literal left-hand-referenced relative direction: ** A style of Western fencing using the main-gauche, i.e. the parrying dagger, normally held in the left hand ** Rive Gauche, on the southern (i.e., left, when facing down th ...

butane is ''syn-clinal'' (''+sc'' or ''–sc'', depending on the

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 ant ...

anti Anti may refer to: *Anti-, a prefix meaning "against" *Änti, or Antaeus, a half-giant in Greek and Berber mythology *A false reading of '' Nemty'', the name of the ferryman who carried Isis to Set's island in Egyptian mythology *Áńt’į, or ...

butane is ''anti-periplanar'', and

eclipsed In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. Such a conformation can exist in any open chain, ...

butane is ''syn-periplanar''.''for textbook discussions of the Klyne–Prelog system, see'' Anslyn, Eric V. and Dougherty, Dennis A. ''Modern Physical Organic Chemistry''. (2005) ''and'' Carroll, Felix. ''Perspectives on Structure and Mechanism in Organic Chemistry''. (2e, 2010)

References

{{DEFAULTSORT:Klyne-Prelog system Stereochemistry Chemical nomenclature