I am looking for the complete rules for drawing molecular orbitals for open chain and cyclic polyenes (neutral, cation, anion) with proper nodes and phases. Appreciate your response.
Very interesting topic. The lead article on this is:
D.F. Bocian, H.L. Strauss, Vibrational spectra, conformations, and potential
functions of cycloheptane and related oxepanes, J. Am. Chem. Soc. 99 (1977) 2866-2878.
The authors found with seven carbons in the ring, the structure is asymmetrical.
We used this information to assign the vibrational modes of the chemical structure of endosulfan, in which there are two isomers: alpha and beta and consistent with Bocian et al work, the symmetrical isomer (beta) is a higher energy conformation. The alpha isomer is a mixture of two asymmetrical conformations. . .
Just saw your message on researchgate. I can help in drawing the orbitals on chemdraw if you still need it. Or should I search some literature on the topic? Sorry for late response.
That would be rather cool! Orbitals must be asymmetrical because in a seven membered ring , the twist form is favored. The only way this becomes symmetrical is because twist can occur in two directions, i.e. a right-handed twist plus a left-handed twist. The previous literature incorrectly assumed there was thus zero twist. Impossible thus to draw orbitals correctly UNLESS two mirror image molecules are being drawn.
Also if one were to draw two forms, one symmetrical (beta-form of endosulfan), one asymmetrical (one of alpha-forms of endosulfan), the summation of the two will ALWAYS be asymmetrical. This is exactly what happens at even the macroscopic level: a right handed twist in alpha- induces a left handed twist on the symmetrical form beta-, so instead of having half symmetrical, half asymmetrical, one has two asymmetrical isomers. Beta- under thermal and/or environmental stress always converts into alpha-isomer forms.
If interesting enough, could even turn into a manuscript for publication. . .