B.R.S.M. The road to Tet. Lett. Is paved with good intentions


And Now For Something Completely Different 10: Don’t Buy Your Undecacycloicosane From Sigma-Aldrich

A funny thing happened the other day: I went onto the Sigma-Aldrich website to order some undecacyclo[,11).0(3,6).0(4,9).0(5,8).0(7,10).0(13,16).0(14,19).0(15,18).0(17,20)]icosane, and was amused to notice a rather M. C. Escher-like rendering of the structure:


Looking for alternative suppliers on Chemspider, I noticed it too had depicted the molecule in quite a strange way (although interestingly their 3D view of the molecule is spot on):

4788435 I guess that both these structures were probably drawn by computers, so I decided to see how Chemdraw's name-to-structure function would deal with such a complicated case. I was certain that the name would either be rejected or that some kind of tortuous hydrocarbon Gordian knot would result, but to my surprise Chemdraw emerged as the clear winner in this bizarre and impromptu competition:

icosane 2

More serious posts soon!

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  1. What the hell is it for? 🙂

    • Probably what milkshake said! I found it by accident while attempting to answer the question, “what’s the lowest molecular weight hydrocarbon that’s a solid at room temperature” using the Sigma-Aldrich website…

      • I think that prize goes to cubane, but tetramethylbutane is a close runner-up. {1.1.1}propellane comes close, having been recrystallized from the melt at 263 K.

  2. it is from the rare chemical library – the stuff that Aldrich bought from old chemical collections at universities. So it was probably only made once, as a part of someone’s thesis.

    Cubanes and all other caged hydrocarbons are interesting for military as dense, high energy fuels, if you could make them for reasonable price. I think exo-isomer of perhydrogenated cyclopentadiene dimer is used as JP-13 experimental fuel.

  3. “I went onto the Sigma-Aldrich website to order some undecacyclo[,11).0(3,6).0(4,9).0(5,8).0(7,10).0(13,16).0(14,19).0(15,18).0(17,20)]icosane”

    …as you do!

  4. A funny thing happened on the way to undecacyclo[,11).0(3,6).0(4,9).0(5,8).0(7,10).0(13,16).0(14,19).0(15,18).0(17,20)]icosane.

    Now say that thrice as fast.

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