How can I name this organic compound while adhering to the IUPAC standards?

A name could not be generated for this structure.

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    $\begingroup$ Congratulations! This structure breaks my favorite structure editor (ChemDoodle) when I attempt to have it name this molecule... $\endgroup$ – Curt F. Feb 16 '16 at 14:07
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    $\begingroup$ Congratulations, this structure breaks ChemDraw's structure-to-name feature too! I'll try LexiChem when I'm at work tomorrow. $\endgroup$ – Geoff Hutchison Feb 16 '16 at 16:11
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    $\begingroup$ I can't even search chemspider with the skeleton (non-aromatic rings) with similarity search (tanimoto 99%) - I get an error. This is the devil's own structure... $\endgroup$ – gilleain Feb 16 '16 at 16:31
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    $\begingroup$ The preferred systematic name in phane nomenclature for the outer ring (without the “1,4-phenylene” bridge) is “1,3,5,7(1,2),2,4,6,8(1,4)-octabenzenacyclooctaphane”. By way of comparison, the similar [8]cycloparaphenylene with the systematic name “1,2,3,4,5,6,7,8(1,4)-octabenzenacyclooctaphane” is described in dx.doi.org/10.1039/c2sc20719b. $\endgroup$ – Faded Giant Feb 16 '16 at 17:22
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    $\begingroup$ I actually suggest issuing this as a Twitter challenge to ChemDraw, OpenEye, ChemDoodle, ACD, etc. $\endgroup$ – Geoff Hutchison Feb 17 '16 at 16:59

It indeed can be named quite nicely using the recent "phane" nomenclature from the Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013, here is the example*

sample schema with structures and names

By abstracting to the bicyclo phane composed of nine benzene nodes ("superatoms") of three kinds, we get

schema with structures


Note that the "superatom" (more precise "amplificant") locant ordering matters. If the numbers in the first parentheses were sorted, it would mean a different structure, that is little bit hard to draw in 2D:

srtucture for the obsolete answer


Publicly accessible references:

*) Please note there is a mistake in the example from the book, the pyridine (4) has wrong internal ring numbering - 4 should be replaced with 5. The name is correct, though. (It is mentioned in errata, for page 310).

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  • $\begingroup$ "[3.3.1] " What does it stand for? $\endgroup$ – Mockingbird Apr 29 '17 at 6:54
  • $\begingroup$ @Mockingbird, "[3.3.1]" describes that the skeleton composed of two cycles (bicyclo) has three branches (that each begin and end in two distinct nodes - it is always the case; here they are X) (therefore three dot-separated numbers) that have 3, 3 (two identical (X)YZY(X) branches) and 1 ((X)Y(X) branch) nodes ("superatoms") respectively, excluding the X end points, total 9 (nonaphane). This type of naming is also used for hydrocarbons, etc. If X, Y and Z were just carbon atom (with hydrogens), it would be bicyclo[3.3.1]nonane. $\endgroup$ – mykhal Apr 29 '17 at 7:46
  • $\begingroup$ @mykkhal what if there are substituents? Like Cl or Br joined to one molecule. $\endgroup$ – Mockingbird Apr 30 '17 at 13:12
  • $\begingroup$ @Mockingbird, numbering is done by indicating the number of the "superatom" and the position on it as upper index, so this structure with chlorine on all peripheral positions would be 1⁴,1⁵,1⁶,2²,2³,3³,3⁴,3⁵,3⁶,4²,4³,5⁴,5⁵,5⁶,6²,6³,7³,7⁴,7⁵,7⁶,‌​8²,8³-docosachloro-1‌​,5(1,3,2),2,4,6,8,9(‌​1,4),3,7(1,2)-nonabe‌​nzenabicyclo[3.3.1]n‌​onaphane $\endgroup$ – mykhal May 9 '17 at 21:45
  • $\begingroup$ "Note that the "superatom" (more precise "amplificant") locant ordering matters. If the numbers in the first parentheses were sorted, it would mean a different structure, that is little bit hard to draw in 2D" Does it only matter for the superatoms by which the "[3.3.1]" is specified? $\endgroup$ – Mockingbird May 10 '17 at 3:51

ChemDoodle 8 can name this via the extended von Baeyer system, although the name is quite long. Thanks for putting up this nice example though!

von Baeyer name


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    $\begingroup$ Although impressive, the name ignores the identity of benzenes and treats the compound as poly-alekene. $\endgroup$ – ssavec Feb 17 '16 at 20:13
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    $\begingroup$ Interesting, Marvin Sketch seems to agree with ChemDoodle and Chem Office can not generate a name at all. $\endgroup$ – Henrique Junior Feb 24 '16 at 16:39

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