The unsymmetrical boat-chair BC conformation of (Z,Z)-cyclonona-1,3-diene is calculated to be 5 kJ mol−1 more stable than the axial-symmetrical twist-boat-chair TBC form; while the calculated energy barrier for limited pseudorotation of BC and TBC is only 10.2kJ mol−1, ring inversion of BCvia plane-symmetrical boat geometry requires 24.4 kJ mol−1.
References
1.
AnetF. A., and YavariI., J. Am. Chem. Soc., 1978, 100, 7814 and refs. therein.
2.
PCMODEL (88.0) Serena Software, Bloomington, IN,
3.
DewarM. J. S., ZeobishE. G., HealyE. F., and StewartJ. J. P., J. Am. Chem. Soc., 1985, 107, 3907.
4.
StewartJ. J. P., J. Comput. Aided Mol. Des., 1990, 4, 1.
5.
StewartJ. J. P., QCPE 581, Department of Chemistry, Indiana University, Bloomington, IN.
6.
DewarM. J. S., HealyE. F., and StewartJ. J. P., J. Chem. Soc., Faraday Trans., 1984, 80, 227.
