Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)

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.

Brief guide to the nomenclature of inorganic chemistry

“…Finally, we note that IUPAC has produced recommendations on the graphical representation of chemical structures and their stereochemical configurations [21,22].…”

Quimioinformática: Uma Introdução

“…Representações gráficas são úteis para que compostos sejam visualizados e compreendidos por seres humanos, mas são ineficientes para um computador capturar e processar a informação contida naquela representação. 29 Diversas representações computacionais de estruturas químicas já foram propostas. Aqui descrevemos as mais inovadoras e importantes.…”

Research Data, Big Data, and Chemistry

“…I began as part of the team producing a new version of the "Red Book", Nomenclature of Inorganic Chemistry-IUPAC Recommendations 2005 [3] and then took on leadership roles in the Division of Chemical Nomenclature and Structure Representation (Division VIII). In those roles I was involved in the development of standards for graphical representation, [4,5] which collectively were guides to drawing chemical structure diagrams that are as unambiguous and informative as possible. I also began to learn more about InChI, particularly about its use in database management/merging.…”

“…This interest in the publication of research data, among other scholarly communication challenges, has spawned a number of new organizations (for example, FORCE11, [1] the Research Data Alliance), [2] which augment long-standing organizations (such as CODATA [3] and ICSU [4]). In addition, repositories for depositing research datasets, such as Data Dryad, [5] As a result of the emerging expectations for researchers to publish data, scientific publishers and research libraries are beginning to offer support services to their communities in navigating this evolving landscape.…”