CHEMICAL NOMENCLATURE AND STRUCTURE REPRESENTATION DIVISION
Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)
Jonathan Brecher
CambridgeSoft Corporation, 100 CambridgePark Drive, Cambridge, MA 02140, USA
Abstract: Stereochemical configuration is determined
by the relationship of atoms in three-dimensional space, yet remains most
commonly represented in two-dimensional media such as printed publications
or computer screens. Recommendations are provided for the display of three-dimensional
stereochemical information in two-dimensional diagrams in ways that avoid
ambiguity and are likely to be understood correctly by all viewers. Examples
are provided for all types of stereochemical configuration, with explanation
of which styles are preferred and which should be avoided. Principal recommendations
include:
- Know your audience: Diagrams that have a wide audience should be drawn
as simply as possible.
- Avoid ambiguous drawing styles.
- Avoid the use of perspective diagrams and class-specific drawing styles
(Fischer projections, Haworth projections, etc.) when structures are to
be interpreted by computers.
- Use solid wedges to indicate bonds that project above the plane of the
paper and hashed wedges to indicate bonds that project below the plane of
the paper; in both cases, the bonds must be oriented with the narrow end
at the stereogenic center.
- Avoid connecting stereogenic centers with a stereobond.
Keywords: graphical representation; configuration; recommendations, stereochemical; IUPAC Chemical Nomenclature and Structure Representation Division; stereochemistry; chirality; chemical structures; chemical structure diagrams.
Download full text of the report [pdf file - 1246 kB]