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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 .
Relative conformation energy diagram of butane as a function of dihedral angle. [8] A: antiperiplanar, anti or trans. B: synclinal or gauche. C: anticlinal or eclipsed. D: synperiplanar or cis. [1] Rotating their carbon–carbon bonds, the molecules ethane and propane have three local energy minima.
The disposition of the formed stereocenters is deemed syn or anti, depending if they are on the same or opposite sides of the main chain: Syn and anti products from an aldol (addition) reaction. The principal factor determining an aldol reaction's stereoselectivity is the enolizing metal counterion.
Anti-periplanar geometry will put a bonding orbital and an anti-bonding orbital approximately parallel to each other, or syn-periplanar. Figure 6 is another representation of 2-chloro-2,3-dimethylbutane (Figure 5), showing the C–H bonding orbital, σ C–H, and the C–Cl anti-bonding orbital, σ* C–Cl, syn-periplanar.
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°).
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When the single bond between the two centres is free to rotate, cis/trans descriptors become invalid. Two widely accepted prefixes used to distinguish diastereomers on sp³-hybridised bonds in an open-chain molecule are syn and anti. Masamune proposed the descriptors which work even if the groups are not attached to adjacent carbon atoms.