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Periplanar or Coplanar?

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Saul Kane and William H. Hersh

Department of Chemistry and Biochemistry, Queens College of the City University of New York, Flushing, NY 11367-1597

J. Chem. Educ., 2000, 77 (10), p 1366

DOI: 10.1021/ed077p1366

Publication Date (Web): October 1, 2000

Section:

History, Education, and Documentation

Abstract

The term "periplanar" was coined by Klyne and Prelog in 1960 to define a flexible torsional angle of 0 Â± 30° (syn) or 180 Â± 30° (anti). The prefix peri, derived from the Greek for "near", was chosen to make the meaning "approximately planar". However, the current common usage of syn and antiperiplanar is planar, which is incorrect. In the interests of proper language, we suggest that future authors instead use "syn-coplanar" and "anti-coplanar".

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Textbooks / Reference Books

Keywords (Subject):

Mechanisms of Reactions

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis and Structural Characterization of Trivalent Amino Acid Derived Chiral Phosphorus Compounds
William H. Hersh, Ping Xu, Cheslan K. Simpson, Jonathan Grob, Brian Bickford, Mohammad Salman Hamdani, Thomas Wood, and Arnold L. Rheingold
The Journal of Organic Chemistry2004 69 (6), 2153-2163
- Synthesis and Structural Characterization of Trivalent Amino Acid Derived Chiral Phosphorus Compounds
  William H. Hersh, Ping Xu, Cheslan K. Simpson, Jonathan Grob, Brian Bickford, Mohammad Salman Hamdani, Thomas Wood, and Arnold L. Rheingold
  The Journal of Organic Chemistry2004 69 (6), 2153-2163
  Reaction of the N-toluenesulfonyl derivatives of (S)-alanine, phenylalanine, and valine (46) with PhPCl2 gave in high yield the 4-methyl, benzyl, and isopropyl derivatives (79) of 2-phenyl-1-p-toluenesulfonyl-1,3,2-oxazaphospholidin-5-one. The ratios of ...
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