DOI QR코드

DOI QR Code

The Molecular Structure and Conformational Stability of Cyclobutylmethyl Ketone by MM2

  • Lee, Mu-Sang (Department of Chemistry, Teachers College, Kyungpook National University) ;
  • Jung, Young-Mee (Department of Chemistry, Teachers College, Kyungpook National University)
  • Published : 1989.06.20

Abstract

The molecular structure of cyclobutylmethyl ketone (c-$C_4H_7COCH_3$) has been investigated by molecular mechanics II (MM2). For the monosubstituted cyclobutane there are two possible ring conformations, the equatorial and axial form, but for the cyclobutylmethyl ketone the equatorial form is predominant conformation. For the $COCH_3$ moiety there are two stable orientations which are the equatorial-gauche and the equatorial-trans form. The equatorial-gauche form where the C = O bond is nearly eclipsing (torsional angle ${\angle}C4-C3-C2-O10=14.5^{\circ}$) one of the ${\alpha}$C-C bonds of the four-membered ring was preferred conformer with steric energy of 13.37 kcal/mol. The equatorial-trans form where the C = O bond is nearly eclipsing (${\angle}C4-C3-C2-O10=145.0^{\circ}$) the ${\alpha}$ C-H bond of the four-membered ring was less stable conformer with steric energy of 15.40 kcal/mol.

Keywords

References

  1. J. Chem. Phys. v.36 W. G. Rothschild;B. P. Dailey
  2. J. Chem. Phys. v.46 J. R. Durig;A. C. Morrissery
  3. J. Chem. Phys. v.47 J. R. Durig;W.H. Green
  4. J. Chem. Phys. v.54 J. R. Durig;J. N. Willis, Jr.;W. H. Green
  5. J. Chem. Phys. v.56 C. S. Blackwell;L. A. Carreira;J. R. Durig;J. M. Karriker;R. C. Lord
  6. J. Chem. Phys. v.57 J. R. Durig;L. A. Carreira;J. N. Willis, Jr.
  7. J. Mol. Struct. v.17 J. R. Durig;A. C. Shing;L. A. Carreira
  8. J. Mol. Struct. v.125 J. R. Durig;H. M. Badawi;T. S. Little;G. A. Guirgis
  9. Quantum Chemistry Program Exchange
  10. J. Am. Chem. Soc. v.89 N. L. Allinger;M.A. Miller;F. A. VanCatledge;J. A. Hirsch
  11. J. Am. Chem. Soc. v.90 N. L. Allinger;J.A. Hirsch;M. A. Miller;I. J. Tymnski;F. A. Van Catledge
  12. J. Am. Chem. Soc. v.93 N. L. Allinger;M. T. Tribble;M. A. Miller;D. H. Wertz
  13. J. Am. Chem. Soc. v.95 E. M. Engler;J. D. Andose;P. von R. Schleyer
  14. J. C. S. Perkin II D. N. J. White;M. J. Bovill
  15. J. Chem. Education v.59 D. B. Boyd;K. b. Lipkowits
  16. Adv. Phys. Org. Chem. v.13 N. L. Allinger
  17. J. Chem. Phys. v.47 E. J. Jacob;H. B. Thompson;L. S. Bartell
  18. J. Am. Chem. Soc. v.87 K. B. Wiberg