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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.
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.
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 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 .
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.
Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used. According to IUPAC, "geometric isomerism" is an obsolete synonym of "cis–trans isomerism". [2]
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The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]