Nomenclature for the C₆₀-I_h and C₇₀-D_5h(6) Fullerenes

Prepared for publication by W. H. Powell, 1436 Havencrest Ct., Columbus, OH, 43220-3841, USA

Members of Working Party (1998-2002): F. Cozzi (Italy) Convenor, G.P. Moss (UK), W.H. Powell (USA), C. Thilgen (Switzerland), R.J.-R. Hwu (Taipei, China), A. Yerin (Russia).

These Rules are as close as possible to the published version [see Pure Appl. Chem., 2002, 74, 629-695. Copyright IUPAC; reproduced with the permission of IUPAC]. If you need to cite these rules please quote this reference as their source.

A PDF of the printed version is available.

For a German translation see Angew. Chem., 2005, 117, 5065-5108.

In setting up the World Wide Web version some errors have been detected. The changes have been marked by which is a link to details of the change and where it applies. For problems in converting the text into a World Wide Web version see the IUPAC nomenclature home page.

Any comments, corrections or suggestions for a future edition should be e-mailed to g.p.moss@qmul.ac.uk

See also Numbering of Fullerenes (IUPAC Recommendations 2004) for the numbering of other fullerenes.

Synopsis

Fullerenes are a new allotrope of carbon characterized by a closed-cage structure consisting of an even number of three-coordinate carbon atoms devoid of hydrogen atoms. This class was originally limited to closed-cage structures with twelve isolated five-membered rings, the rest being six-membered rings.

Although it was recognized that existing organic ring nomenclature could be used for these structures, the resulting names would be extremely unwieldy and inconvenient for use. At the same time, it was also recognized that established organic principles could be used, or adapted, to provide a consistent nomenclature for this unique class of compounds based on the class name fullerene. However, it was necessary to develop an entirely new method for uniquely numbering closed-cage systems.

This paper describes IUPAC recommendations for naming and uniquely numbering the two most common fullerenes with isolated pentagons, the icosahedral C₆₀ fullerene and the D_5h(6)-C₇₀ fullerene. It also describes recommendations for adapting organic nomenclature principles for naming fullerenes with nonclosed-cage structures, heterofullerenes, derivatives formed by substitution of hydrofullerenes, and the fusion of organic rings or ring systems to the fullerene cage. Finally, this paper suggests methods for describing structures consisting of two or more fullerene units and for denoting configurations of chiral fullerenes and their derivatives.

Contents

• Fu-0. Introduction
• Fu-1. Definitions
  • Fu-1.1. Fullerenes
  • Fu-1.2. Fulleranes
  • Fu-1.3. Fulleroids
• Fu-2. Names
  • Fu-2.1. Systematic names
  • Fu-2.2. Trivial names
• Fu-3. Numbering
  • Fu-3.1. Systematic numbering
  • Fu-3.2. Systematic numbering for (C₆₀-I_h)[5,6]fullerene
  • Fu-3.3. Systematic numbering for (C₇₀-D_5h(6))[5,6]fullerene
  • Fu-3.4. Trivial numbering
• Fu-4. Structurally Modified Fullerenes
  • Fu-4.1. Homofullerenes
  • Fu-4.2. Norfullerenes
  • Fu-4.3. Secofullerenes
  • Fu-4.4. Cyclofullerenes
  • Fu-4.5. Combinations of structure-modifying prefixes
• Fu-5. Heterofullerenes
  • Fu-5.1. Skeletal replacement ('a') nomenclature for fullerenes
  • Fu-5.2. Skeletal replacement ('a') nomenclature for structurally modified fullerenes
• Fu-6. Fullerene Derivatives
  • Fu-6.1. Fulleranes
  • Fu-6.2. Fullerenes
  • Fu-6.3. Lowest locants
  • Fu-6.4. Fullerenes and fulleranes as substituents
  • Fu-6.5. endo-Substituted fullerenes and fulleranes
• Fu-7. Fullerenes and Modified Fullerenes Fused to Organic Rings or Ring Systems
• Fu-8. Bridged Fullerenes
• Fu-9. Spiro Fullerenes
• Fu-10. Fullerene Structures with Two Fullerene Components
  • Fu-10.1. Bridged and fused two-component fullerenes
  • Fu-10.2. Fullerene ring assemblies
  • Fu-10.3. Fullerene ring assemblies plus the prefix 'cyclo'
  • Fu-10.4. Spiro homo and fused ring fullerenes
• Fu-11. Fullerene Structures with Three or More Fullerene Components
• Fu-12. Fullerenes in Coordination Compounds
• Fu-13. Fullerenes in Polymers
• Fu-14. Fullerene Cations
• Fu-15. Fullerene Radical Ions
• Fu-16. Metal Derivatives of Fullerenes
• Fu-17. Configurational Specification for the C₆₀-I_h and C₇₀-D_5h(6) Fullerenes and Their Derivatives
  • Fu-17.1. Types of chiral fullerenes
  • Fu-17.2. The substitution test
  • Fu-17.3. Principles of the descriptor system
  • Fu-17.4. Achiral parent fullerenes with an inherently chiral substitution pattern
  • Fu-17.5. Achiral parent fullerenes with a noninherently chiral substitution pattern
  • Fu-17.6. Fullerene derivatives with achiral substitution patterns and chiral substituents
  • Fu-17. 7. Superimposition of stereogenic elements in a fullerene molecule
• References