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. Author manuscript; available in PMC: 2012 Oct 7.
Published in final edited form as: J Org Chem. 2011 Sep 6;76(19):7933–7937. doi: 10.1021/jo201389d

TABLE 1.

n→π* Interaction in Conformations 1–8

Conformation Relative Energies (kcal/mol) d (Å) θ (º) En→π* (kcal/mol)1 En→π* (kcal/mol)2
1 0.00 2.83 96.3 1.73 1.36
2 0.84 2.89 96.8 0.95 0.95
3 3.39 3.05 66.5 0.21 0.16
4 5.29 3.07
3.01		 92.3
94.8		 0.16
0.28		 0.13
0.23
5 5.32 3.00 113.1 1.03 0.79
6 5.49 2.95 110.4 0.70 0.82
7 — 2.71 104.6 4.87 3.57
83 — 3.19 124.6 0.52 0.32
1

Second-order perturbative estimates.

2

From deletion analysis.

3

Less stable than conformation 7 by 1.10 kcal/mol.