Ab initio HF/6-31G* and MP2/6-31G*//HF/6-31G* methods were used to calculate the relative energies of the important energy-minimum conformations and transition-state geometries of (Z,E,Z)-cyclonona-1,3,5-triene; the calculated energy barrier for ring inversion of the twist–chair (C1) conformation is 29.35 kJ/mol, while the barrier for swivelling of the trans double bond through the polymethylene bridge is 59.76 kJ/mol.
DaubenW.G., MichnoD. M., and OlsenE. G., J. Org. Chem., 1981, 46, 687.
2.
AnetF.A. L., and KozerskiL., J. Am. Chem. Soc., 1973, 95, 3407.
3.
AnetF.A. L., and YavariI., J. Am. Chem. Soc., 1978, 100, 7814.
4.
AnetF.A. L., and YavariI., J. Am. Chem. Soc., 1977, 99, 6986.
5.
ShimizuT., IwataK., KamigataN., and IkutaS., J. Chem. Res. (S), 1994, 436.
6.
ErmerO., J. Am. Chem. Soc., 1976, 98, 3964.
7.
ElielE.L., and WilenS. H., Stereochemistry of Organic Compounds; Wiley, 1994, pp. 1172–1173.
8.
PawarD. M., MigginsS. D., SmithS. V., and NoeE. A., J. Org. Chem., 1999, 64, 2418.
9.
AnetF.A. L., and YavariI., J. Am. Chem. Soc., 1977, 99, 6496.
10.
YavariI., Kabiri-FardH., and MoradiSh., J. Chem. Res. (S), 2000, 384.
11.
FreemanF., PhornvoranuntA., and HehreW. J., J. Phys. Org. Chem., 1998, 11, 831.
12.
GilbertT.M., Tetrahedron Lett., 1998, 39, 9147.
13.
RemkoM., LyneP. D., and RichardsW. G., Phys. Chem. Chem. Phys., 1999, 1, 5353.
14.
StricklandA.D., and CaldwellR. A., J. Phys. Chem., 1993, 97, 13394.
15.
ArnasonI., ThorarinssonG. K., and MaternE., J. Mol. Struct. (Theochem), 1998, 454, 91.
16.
Gaussian 98, Revision A. 6, FrischM.J., TrucksG.W., SchlegelH.B., ScuseriaG.E., RobbM.A., CheesemanJ.R., ZakrzewskiV.G., MontgomeryJ.A.Jr., StartmannR.E., BurantJ.C., DapprichS., MillamJ. M., DanielsA. D., KudinK. N., StrainM. C., FarkasO., TomasiJ., BaroneV., CossiM., CammiR., MennucciB., PomelliC., AdamoC., CliffordS., OchterskiJ., PeterssonG. A., AyalaP. Y., CuiQ., MorokumaK., MalickD. K., RubuckA. D., RaghavachariK., ForesmanJ. B., CioslowskiJ., OritzJ. V., StefanovB. B., LiuG., LiashenkoA., PiskorzP., KomaromiI., CompertsR., MartinR. L., FoxD. J., KeithT., Al-LahamM. A., PengC. Y., NanayakkaraA., GonzalezC., ChallacombeM., GillP. M. W., JohnsonB., ChenW., WongM. W., AndresJ. L., GonzalezC., Head-GordonM., ReplogleE. S., and PopleJ. A., Gaussian. Inc., Pittsburgh PA1998.
17.
JensenF., Introduction to Computational Chemistry, Wiley, New York, 1999; W. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople., Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
18.
HariharanP.C., PopleJ. A., Theor. Chim. Acta, 1973, 28, 213.