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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. [9] A: antiperiplanar, anti or trans. B: synclinal or gauche. C: anticlinal or eclipsed. D: synperiplanar or cis. [2] Rotating their carbon–carbon bonds, the molecules ethane and propane have three local energy minima.
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.
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).
The prefix endo is reserved for the isomer with the substituent located closest, or "syn", to the longest bridge. The prefix exo is reserved for the isomer with the substituent located farthest, or "anti", to the longest bridge. Here "longest" and "shortest" refer to the number of atoms that comprise the bridge.
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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.
This image of a simple structural formula is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship.