Skip to main content
SpringerLink
Log in

Introduction

  • Chapter
The Chemistry of Rotational Isomers

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 30))

  • 111 Accesses

Abstract

It was a historical breakthrough when van’t Hoff [1] and LeBel [2] were able to explain the existence of enantiomers in carbon compounds by assuming the tetrahedral arrangement of four ligands about the carbon atom. Although it took sometime for the theory to be accepted by the chemical world, it became the general concept that the carbon atoms take on a tetrahedral spatial arrangement and the organic molecules should be treated as three dimensional objects. The reason for this is the easy understanding of the optical activity of isomeric molecules which differ only in the direction of optical rotation but possess identical properties in other chemical and physical aspects.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. van’t Hoff JH (1874) Arch Neerl Sci Exact 9: 445

    Google Scholar 

  2. (1875) Bull soc chim France 23: 295

    Google Scholar 

  3. Le Bel JA (1874) Bull soc chim France 22: 337

    Google Scholar 

  4. van’t Hoff JH (1875) La chimie dans l’espace, Bazendijk, Rotterdam

    Google Scholar 

  5. Mizushima S, Morino Y, Higashi K (1934) Sci Pap Inst Phys Chem Res 25: 159

    CAS  Google Scholar 

  6. Kemp JD, Pitzer KS (1936) J Chem Phys 4: 749.

    Article  CAS  Google Scholar 

  7. (1937) J Am Chem Soc 59: 276

    Article  CAS  Google Scholar 

  8. Dauben W, Pitzer KS (1956) Conformational analysis. In: Newman MS (ed) Steric effects in organic chemistry. Wiley, New York, p 1

    Google Scholar 

  9. Evans MW (1974) Spectrochim Acta 30A: 79

    Google Scholar 

  10. Eliel EL (1976) Isr J Chem 15: 7

    Google Scholar 

  11. Lide DR Jr, Christensen D (1961) J Chem Phys 35: 1374

    Article  CAS  Google Scholar 

  12. Whangbo M-H, Schlegel HB, Wolfe S (1977) J Am Chem Soc 99: 1296

    Article  CAS  Google Scholar 

  13. Kondo S, Hirota E, Morino Y (1974) J Mol Spectrosc 28: 471

    Article  Google Scholar 

  14. Christie GH, Kenner J (1922) J Chem Soc 121: 614

    Article  CAS  Google Scholar 

  15. Kuhn R (1933) Molekulare Asymmetrie. In: Freudenberg H (ed) Stereochemie. Franz Deutike, Leipzig, p 803

    Google Scholar 

  16. Mizushima S (1954) Structure of molecules and internal rotation, Academic, New York

    Google Scholar 

  17. Jensen FR, Bushweller CH (1966) J Am Chem Soc 88: 4279

    Article  CAS  Google Scholar 

  18. Hofner D, Lesko SA, Binsch G (1978) Org Magn Reson 11: 179

    Article  Google Scholar 

  19. Tanigaki K, Yagi M, Higuchi J (1989) J Magn Reson 84: 282

    CAS  Google Scholar 

  20. Lister DG, Macdonald JN, Owen NL (1978) Internal rotation and inversion, Academic, London

    Google Scholar 

  21. Kessler H (1970) Angew Chem 82: 237

    Article  Google Scholar 

  22. Angew Chem Int Ed Engl 9: 219.

    Article  CAS  Google Scholar 

  23. Binsch G (1975) Band shape analysis. In Jackman LM, Cotton FA (eds), Dynamic nuclear magnetic resonance spectroscopy, Academic, New York, p 45

    Google Scholar 

  24. Pitzer KS (1940) Chem Rev 27: 39

    Article  CAS  Google Scholar 

  25. Hoogasian S, Bushweller CH, Anderson WG, Kingsley G (1976) J Phys Chem 80: 643.

    Article  CAS  Google Scholar 

  26. Anderson JE, Doeck CW, Pearson H, Rawson DI (1978) J Chem Soc, Perkin II, 974

    Google Scholar 

  27. Brownstein S, Dunogues J, Linsay D, Ingold KU (1977) J Am Chem Soc 99: 2073

    Article  CAS  Google Scholar 

  28. Flamm-ter Meer MA, Beckhaus H-D, Peters K, von Schnering H-G, Fritz H, Rüchardt C (1986) Chem Ber 119: 1492

    Article  CAS  Google Scholar 

  29. Adams R, Yuan HC (1933) Chem Rev 12: 261

    Article  CAS  Google Scholar 

  30. Hawkins BL, Bremser W, Borsic S, Roberts JD (1971) J Am Chem Soc 93: 4472

    Article  Google Scholar 

  31. ref 19aa.

    Article  Google Scholar 

  32. ref 19ab.

    Article  CAS  Google Scholar 

  33. Ōki M (1983) Top Stereochem 14: 1

    Article  Google Scholar 

  34. Gibbons WA, Gil VMS (1965) Mol Phys 9: 163

    Article  CAS  Google Scholar 

  35. Anderson JE, Franck RW, Mandella WL (1972) J Am Chem Soc 94: 1880

    Google Scholar 

  36. Lomas JS, Dubois JE (1976) J Org Chem 41: 3033

    Article  CAS  Google Scholar 

  37. Stewart WE, Siddall TH, III (1970) Chem Rev 70: 517

    Article  CAS  Google Scholar 

  38. Sandström J (1983) Top Stereochem 14: 83

    Article  Google Scholar 

  39. Brewer JPN, Eckhart IF, Heaney H, Marples BA (1968) J Chem Soc C 664

    Google Scholar 

  40. Ōki M, Suda M (1971) Bull Chem Soc Jpn 44: 1876

    Article  Google Scholar 

  41. Yamamoto G, Nakamura M, Ōki M (1975) Bull Chem Soc Jpn 48: 2592

    Article  CAS  Google Scholar 

  42. Toyota S, Yamane H, Ōki M (1993) Bull Chem Soc Jpn 66: in press

    Google Scholar 

  43. Yamamoto G, Ōki M (1975) Bull Chem Soc Jpn 48: 3686

    Article  CAS  Google Scholar 

  44. Siddall TH III, Stewart WE (1969) J Org Chem 34: 233

    Article  CAS  Google Scholar 

  45. Chandross EA, Sheley CF Jr (1968) J Am Chem Soc 90: 4345

    Article  CAS  Google Scholar 

  46. Rieker A, Kessler H (1969) Tetrahedron Lett 1227

    Google Scholar 

  47. Nakamura M, Nakamura N, Ōki M (1977) Bull Chem Soc Jpn 50: 1097

    Article  CAS  Google Scholar 

  48. Nakamura M, Ōki M (1974) Tetrahedron Lett 505.

    Google Scholar 

  49. Murata S, Kanno S, Tanabe Y, Nakamura M, Ōki M. (1982) Bull Chem Soc Jpn 55: 1522

    Article  CAS  Google Scholar 

  50. Mannschreck A, Ernst L (1971) Chem Ber 104: 228

    Article  CAS  Google Scholar 

  51. Murata S, Mori T, Ōki M (1984) Bull Chem Soc Jpn 57: 1970

    Article  CAS  Google Scholar 

  52. Urushibara Y (1947) Lecture Note. University of Tokyo. The main work described in this book was inspired by this lecture.

    Google Scholar 

  53. Mislow K (1950) Science 112: 26

    Article  CAS  Google Scholar 

  54. Gawronski J, Gawronska K, Rychlewska U (1989) Tetrahedron Lett 30: 6071

    Article  CAS  Google Scholar 

  55. Curtin DY (1954) Rec Chem Progr 15: 111

    CAS  Google Scholar 

  56. Hammett LP (1970) Physical organic chemistry, 2nd edn, McGraw-Hill, New York, p 119

    Google Scholar 

  57. Lucas HJ, Simpson TP, Carter JM (1925) J Am Chem Soc 47: 1462

    Article  CAS  Google Scholar 

  58. Curtin DY, Kellom DB (1953) J Am Chem Soc 75: 6011

    Article  CAS  Google Scholar 

  59. Seeman JI (1983) Chem Rev 83: 83

    Article  CAS  Google Scholar 

  60. Winstein S, Holness NJ (1955) J Am Chem Soc 77: 5562.

    Article  CAS  Google Scholar 

  61. Eliel EL, Lukach CA (1957) J Am Chem Soc 79: 5986

    Article  CAS  Google Scholar 

  62. Gold V, Loening KL, McNaught AD, Sehmi P (eds) (1987) Compendium of chemical terminology (IUPAC Recommendations), Blackwell, Oxford

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Okayama University of Science, Okayama 700, Japan

    Professor Michinori Ōki

Authors
  1. Professor Michinori Ōki
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1993 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Ōki, M. (1993). Introduction. In: The Chemistry of Rotational Isomers. Reactivity and Structure Concepts in Organic Chemistry, vol 30. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-51024-3_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-51024-3_1

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-51026-7

  • Online ISBN: 978-3-642-51024-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation