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Cyclohexane: Boat Form Revisited

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Ronald R. Sauers

Department of Chemistry, Rutgers, the State University, New Brunswick, NJ 08903

J. Chem. Educ., 2000, 77 (3), p 332

DOI: 10.1021/ed077p332

Publication Date (Web): March 1, 2000

Section:

History, Education, and Documentation

Abstract

Organic chemistry textbooks often cite an outdated structure for the boat conformer of cyclohexane that is based on ideal bond angles and distances. Density functional computations carried out at the B3LYP/6-311++G(2d,p) level on this conformer show that the structure is more open than previously supposed, with a flagpole H-H distance of 2.35 Å. As a consequence, the high energy of this transition state is better attributed to the eclipsed butane torsion interactions and flagpole C-C nonbonded interactions.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Pedagogy):

Misconceptions / Discrepant Events

Keywords (Subject):

Computational Chemistry

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

Toward Consistent Terminology for Cyclohexane Conformers in Introductory Organic Chemistry
Donna J. Nelson , Christopher N. Brammer
Journal of Chemical Education2011 88 (3), 292-294
- Toward Consistent Terminology for Cyclohexane Conformers in Introductory Organic Chemistry
  Donna J. Nelson , Christopher N. Brammer
  Journal of Chemical Education2011 88 (3), 292-294
  Recommended changes in use of cyclohexane conformers and their nomenclature will remedy inconsistencies in cyclohexane conformers and their nomenclature that exist across currently used organic chemistry textbooks. These inconsistencies prompted this ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Interconvertions between δ-Lactam and δ-Lactone Derivatives Initiated by Unique Transannular Interactions of the Rigid Cyclohexane Boat Structure in Pentacycloundecane
Hendrik G. Kruger, Frans J. C. Martins, and Agatha M. Viljoen
The Journal of Organic Chemistry2004 69 (14), 4863-4866
- Interconvertions between δ-Lactam and δ-Lactone Derivatives Initiated by Unique Transannular Interactions of the Rigid Cyclohexane Boat Structure in Pentacycloundecane
  Hendrik G. Kruger, Frans J. C. Martins, and Agatha M. Viljoen
  The Journal of Organic Chemistry2004 69 (14), 4863-4866
  The pentacycloundecane (PCU) cage structure resembles a perfect boat conformation, and for the first time unique lactam/lactone interconversions on the flagpole carbons of a cyclohexane boat structure are reported. The syntheses of a novel dihydroxy-PCU-δ-...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links