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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 .
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.
syn/anti peri/clinal. a torsion angle between 0° and ±90° is called syn (s) a torsion angle between ±90° and 180° is called anti (a) a torsion angle between 30° and 150° or between −30° and −150° is called clinal (c) a torsion angle between 0° and ±30° or ±150° and 180° is called periplanar (p)
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.
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The syn-conformation shown above, with a dihedral angle of 60° is less stable than the anti-conformation with a dihedral angle of 180°. For macromolecular usage the symbols T, C, G +, G −, A + and A − are recommended (ap, sp, +sc, −sc, +ac and −ac respectively).
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