Other Configuration Notations

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Fischer projection formulas are particularly useful for comparing configurational isomers within a family of related chiral compounds, such as the carbohydrates. However, the eclipsed conformations implied by these representations are unrealistic. When describing acyclic compounds incorporating two or more chiral centers, many chemists prefer to write zig-zag line formulas for the primary carbon chain. Here, the zig-zag carbon chain lies in a plane and the absolute or relative configurations at the chiral centers are then designated by wedge or hatched bonds to substituent groups. This is illustrated for D-(-)-ribose and the diastereoisomeric D-tetroses erythrose and threose in the following diagram.

These compounds are all chiral and only one enantiomer is drawn (the D-family member). Many times, however, we must refer to and name diastereoisomers that are racemic or achiral. For example, addition of chlorine to cis-2-butene yields a stereoisomer of 2,3-dichlorobutane different from the one obtained by chlorine addition to trans-2-butene. In cases having two adjacent chiral centers, such as this, the prefixes erythro and threo may be used to designate the relative configuration of the centers. These prefixes, taken from the names of the tetroses erythrose and threose (above), may be applied to racemic compounds, as well as pure enantiomers and meso compounds, as shown in the following diagram. In the commonly used zig-zag drawings substituents may lie on the same side of the carbon chain, a syn orientation, or on opposite sides, an anti orientation. For adjacent (vicinal) substituents this is opposite to their location in a Fischer formula. Thus, the substituents in the erythro isomer have an anti orientation, but are syn in the threo isomer.

The syn-anti nomenclature may be applied to acyclic compounds having more than two chiral centers, as illustrated by the example in the colored box. The stereogenic center nearest carbon #1 serves as a reference. At sites having two substituents, such as carbon #5, the terms refer to the relative orientation of the highest order substituent, as determined by the C.I.P. sequence rules.

Contributors

William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry