Absolute helicities of twisted 9,10-phenanthrenequinones.

Fritsch, Rainer; Hartmann, Erwin; Brandl, G.; Mannschreck, Albrecht

doi:10.1016/s0957-4166(00)86088-7

Cited by 6 publications

(1 citation statement)

References 32 publications

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“…Here, X-ray and AM llab initiu data disagree by cn. 5" for Bcxt while Bin, and the Y values compare very well with each other. To get more insight into these discrepancies we have investigated the computationally very expensive decachlorine-substituted compound 3a for which X-ray data are also available.…”

Section: And ~2 " ;supporting

confidence: 58%

X-Ray and quantum chemical studies of strained phenanthrenes

Pischel¹,

Nieger²,

Vögtle³

1996

J. Chem. Soc., Perkin Trans. 2

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The synthesis of the highly strained helical 4-tert-butyl-1,5,8-trimethylphenanthrene 6 was achieved by photochemically induced dehydrocyclization. The helical deformation of the aromatic carbon skeleton in the reported X-ray structure is found to be 36.6" which is the largest value found for a phenanthrene hydrocarbon. A systematic yuan tum chemical investigation of strained 4,S-substit u ted phenanthrene derivatives (R, R': F, Cl, methyl, tert-butyl) at ab initiu Hartree-Fock and semiempirical AM1 theoretical levels is presented. The geometrical parameters describing the strain in these helical molecules are compared with X-ray data from the literature and are found to be generally in good agreement. Substantial deviations between theory and experiment for the helical deformation angles are observed in the case of the chlorinesubstituted molecules (ca. 5") which indicates the importance of crystal packing effects. A prediction of the structure of the unknown 4,5-di-tert-butylphenanthrene 5, that could be detected by GC-MS, but has not been isolable so far is also given. The total strain energies of 5 and 6 are calculated to be 49.6 and 34.0 kcal mol-', respectively, and are distributed to non-bonded and aromatic ring deformation contributions.

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Section: And ~2 " ;supporting

confidence: 58%

X-Ray and quantum chemical studies of strained phenanthrenes

Pischel¹,

Nieger²,

Vögtle³

1996

J. Chem. Soc., Perkin Trans. 2

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Chiroptical Properties of Compounds ContainingCOGroups

Boiadjiev

Lightner

2009

Patai's Chemistry of Functional Groups

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Introduction The Octant Rule Compilation of Ketone and Aldehyde CD Unsaturated Ketones Compilation of Unsaturated Ketone and Aldehyde CD Exciton Chirality Addendum Acknowledgments

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