Cis and trans isomers of cycloalkenes

Journal of Chemical Education

Volumn 82, Issue 9, 2005, Pages 1334-1339

  Barrows, Susan E ^a   Eberlein, Thomas H ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPUTATIONAL METHODS; HYDROGENATION; ISOMERS; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; OPTIMIZATION;

BOND ANGLES; BOND LENGTH; CYCLOALKENES; RELATIVE ENERGIES;

OLEFINS;

EID: 24144436206     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed082p1334     Document Type: Article

References (27)

1. Hehre, W. J.; Shusterman, A. J.; Nelson, J. E. The Molecular Modeling Workbook for Organic Chemistry; Wavefunction Inc.: Irvine, CA, 1998.
2. Carey, F. A. Organic Chemistry, 5th ed.; McGraw-Hill: New York, 2003; p 201.
3. Hornback, J. M. Organic Chemistry, 1st ed.; Brooks/Cole: Pacific Grove, CA, 1998; p 210.
4. Brown, W. H.; Foote, C. S.; Organic Chemistry, 3rd ed.; Brooks/ Cole: Pacific Grove, CA, 2002; p 167.
5. Barrows, S. E. Eberlein, T. H. J. Chem. Educ. 2004, 81, 1529-1532.
6. Cope, A. C.; Moore, P. T.; Moore, W. R. J. Am. Chem. Soc. 1960, 82, 1744.
7. Turner, R. B.; Meador, W. R. J. Am. Chem. Soc. 1957, 79, 4133-4136.
8. Cope, A. C.; Moore, P. T.; Moore, W. R. J. Am. Chem. Soc. 1959, 81, 3153.
9. (cis-cyclooctene) Mastryukov, V. S.; Chen, K.; Allinger, N. L. J. Phys. Chem. A 2001, 105, 8562-8566.
10. (trans-cyclooctene) Cope, A. C.; Moore, P. T.; Moore, W. R. J. Am. Chem. Soc. 1959, 81, 3153.
11. Ermer, O.; Mason, S. A. Acta Cryst. 1982, B38, 2200-2206.
12. Trætteberg, M. Acta Chem. Scand. 1975, B29, 29-36.
13. (cis-cydononene) Pawar, D. M.; Miggins, S. D.; Smith, S. V.; Noe, E. A. J. Org. Chem. 1999, 64, 2418-2421.
14. (cis-cyclodecene) Pawar, D. M.; Noe, E. A. J. Am. Chem. Soc. 1998, 120, 5312-5314.
15. (trans-cyclodecene) Pawar, D. M.; Noe, E. A. J. Am. Chem. Soc. 1996, 118, 12821-12825.
16. The molecular structure of trans-cyclooctene was determined in 1975 by electron diffraction: Trætteberg, M. Acta Chem. Scand. 1975, B29, 29.
17. The molecular geometry was predicted in 1958 from dipole moment measurements and infrared spectroscopy data: Allinger, N. L. J. Am. Chem. Soc. 1958, 80, 1953.
18. Allinger, N. L.; Sprague, J. J. Am. Chem. Soc. 1972, 74, 5734.
19. Leong, M. K.; Mastryukov, V. S.; Boggs, J. E. J. Mol. Struct. 1998, 445, 149-160.
20. Eaton, P. E.; Maggini, M. J. Am. Chem. Soc. 1988, 110, 7230.
21. Leong, M. K.; Mastryukov, V. S.; Boggs, J. E. J. Mol. Struct. 1998, 445, 149-160.
22. Haddon, R. C. J. Am. Chem. Soc. 1987, 109, 1676-1685.
23. Houk, K. N. Isr. J. Chem. 1983, 23, 3-9, and refs therein.
24. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4057.
25. Titan ver. 1.0.5, Wavefunction, Inc. http://www.wavefun.com; Schrodinger, Inc., http://www.schrodinger.com/(accessed Jul 2005).
26. Barrows, S. E.; Eberlein, T. H. J. Chem. Educ. 2005, 82, 1329-1333.
27. Cis and Trans Isomerization in Cyclic Alkenes. http://www.personal. psu.edu/sebl6/cycloalkenes (accessed Jul 2005).