Monday, January 7, 2019

IUPAC nomenclature for an interesting looking organic compound


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


A name could not be generated for this structure.




Answer



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


1,5(1,3,2),2,4,6,8,9(1,4),3,7(1,2)-nonabenzenabicyclo[3.3.1]nonaphane


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



1,5(1,2,3),2,4,6,8,9(1,4),3,7(1,2)-nonabenzenabicyclo[3.3.1]nonaphane


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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