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Precision in Stereochemical Terminology

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LeRoy G. Wade Jr.

Department of Chemistry, Whitman College, Walla Walla, WA 99362

J. Chem. Educ., 2006, 83 (12), p 1793

DOI: 10.1021/ed083p1793

Publication Date (Web): December 1, 2006

Section:

History, Education, and Documentation

Abstract

Many organic chemists have begun to use the Mislow term stereocenter (or stereogenic atom) as an alternative to the traditional term asymmetric carbon atom and the slightly broader IUPAC term chirality center. But the term stereocenter is defined much more broadly. It includes a wide variety of structures that are neither chirality centers nor asymmetric carbon atoms. The rules that students learn about asymmetric carbon atoms are no longer true when one substitutes the broader term stereocenter. Asymmetric carbon atoms are defined structurally, and students can easily find them to use as a tool to help in understanding the stereochemistry and finding the stereoisomers. In contrast, students must already know which stereoisomers exist to identify the stereocenters. This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

Chemical Principles Revisited

Keywords (Pedagogy):

Misconceptions / Discrepant Events

Keywords (Subject):

Chemical Technicians

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Citing Articles

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

The Protocenter Concept: A Method for Teaching Stereochemistry
David E. Lewis
Journal of Chemical Education2010 87 (6), 604-607
- The Protocenter Concept: A Method for Teaching Stereochemistry
  David E. Lewis
  Journal of Chemical Education2010 87 (6), 604-607
  The protocenter, defined as an atom carrying two different attached groups in a nonlinear arrangement, is proposed as a concept useful for the introduction of chirality and geometric isomerism in introductory organic chemistry classes. Two protocenters ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
The Meaning of Meso
Addison Ault
Journal of Chemical Education2008 85 (3), 441
- The Meaning of Meso
  Addison Ault
  Journal of Chemical Education2008 85 (3), 441
  The original use of the prefix "meso" was to refer to an optically inactive, non-resolvable member of a set of stereoisomers, some of which were optically active. More recently there have been attempts to define meso in terms of the structural features ...
  Abstract | Hi-Res PDF | PDF w/ Links