Computation of the Configurational Descriptors of C₆₀ and C₇₀ Derivatives with a Chiral Functionalization Pattern

by Lubomir Sebo & Carlo Thilgen (ETH Zürich)

The following interactive pages have been prepared to facilitate the determination of the configuration of C₆₀ or C₇₀ derivatives with a chiral functionalization pattern according to the procedure given in the paper 'Configurational Description of Chiral Fullerenes and Fullerene Derivatives with a Chiral Functionalization Pattern', C. Thilgen, A. Herrmann, F. Diederich, Helv. Chim. Acta 1997, 80, 183-199.

See also: W. H. Powell, F. Cozzi, G. P. Moss, C. Thilgen, R. J.-R. Hwu, A. Yerin, Pure Appl. Chem. 2002, 74, 629-695. Nomenclature for the C₆₀-I_h and C70-D_5h(6) fullerenes (IUPAC recommendations 2002). A world wide web html-version of these recommedations has been prepared by G. P. Moss.

Input

Input the locants taken from a CLOCKWISE (^fC ) numbering scheme (for example a Schlegel diagram with numbered atoms) of C₆₀ or C₇₀: They do not necessarily have to represent the lowest set of locants, just take care that the relative positions of the introduced addends/substituents are correct.

If the addition pattern is noninherently chiral, you have to include the CIP (Cahn, Ingold, Prelog) priorities of the addends in the form "locant.priority", e.g., "4.02" for an addend/substituent in position 4 with the priority 2. If you are not sure whether a functionalization pattern is inherently or non-inherently chiral, you should include the priority of each addend in your input.

Output  -  it includes

• The type of chirality of the functionalization pattern
• If applicable, the configurational descriptor (^fA or ^fC ) for the functionalization pattern
• The lowest set of locants corresponding to the functionalization pattern (this works also with achiral functionalization patterns)

Choose between the systematic and the trivial numbering schemes/descriptors

Temporarily out of order

• C₆₀ -  IUPAC / CAS numbering (systematic numbering)
• C₇₀ -  IUPAC / CAS numbering (systematic numbering)
  >> Descriptors: ^f,sA or ^f,sC ('f' = fullerene, 's' = systematic [numbering])
  

• C₆₀ -  Taylor numbering (trivial numbering)
• C₇₀ -  Taylor numbering (trivial numbering)
  >> Descriptors: ^f,tA or ^f,tC ('f' = fullerene, 't' = trivial [numbering])

For details on fullerene numbering schemes, see:

W. H. Powell, F. Cozzi, G. P. Moss, C. Thilgen, R. J.-R. Hwu, A. Yerin, Pure Appl. Chem. 2002, 74, 629-695 (Nomenclature for the C₆₀-I_h and C70-D_5h(6) fullerenes - IUPAC recommendations 2002) and the corresponding world wide web html-version of these recommedations.

Please report bugs or comments to:

http://www.diederich.chem.ethz.ch/chirafull/