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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)

Jonathan Brecher1

1CambridgeSoft Corporation, 100 CambridgePark Drive, Cambridge, MA 02140, USA

Project Year: 2003, Project Code: 2003-045-3-800

Citation Information: Pure and Applied Chemistry. Volume 78, Issue 10, Pages 1897–1970, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: 10.1351/pac200678101897, January 2009

Publication History

Published Online:

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: chemical structure diagrams; chemical structures; chirality; configuration; graphical representation; IUPAC Chemical Nomenclature and Structure Representation Division; nanodevices; recommendations; stereochemical; stereochemistry


  • 1

    2013, 2, 3, S. 150 [CrossRef], WilliamsAntony John, YerinAndrey, Wiley Interdisciplinary Reviews: Computational Molecular Science, WIREs Comput Mol Sci, 17590876, Automated systematic nomenclature generation for organic compounds

  • 2

    2011, 4, 1, S. 557 [CrossRef], WarrWendy A., Wiley Interdisciplinary Reviews Computational Molecular Science, WIREs Comput Mol Sci, 17590876, Representation of chemical structures

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