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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.
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.
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 .
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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These proceed in a suprafacial-antarafacial sense (syn/anti stereochemistry), such as the cycloaddition reactions of ketene and allene derivatives, in which the orthogonal set of p orbitals allows the reaction to proceed via a crossed transition state, although the analysis of these reactions as [π 2 s + π 2 a] is controversial.
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