Bis, Tris, Tetrakis

For many seasons, Th’ Gaussling was the keeper of part numbers and nomenclature in his village.  Fellow peasants would stumble out from the dark and dank mines to plead for new part numbers and names for the new products. As always, outsiders are surprised to learn that this is an actual “job”, but in fact it is. When you make new stuff, eventually you have to call it something. And what you call it has to be recognizable to the barbarian tribes outside the walls.

Peasants and grandees alike would take the names in gratitude for the everpresent fear was that they themselves would be called to toil in the muck of nomenclature as I have.

The dark world of nomenclature is split into two hemispheres- IUPAC and CAS. I don’t know what the deal is with Beilstein. It seems to be a sinking ship with a few deckhands polishing the brass knobs as the bow submerges.  Arguably, CAS has become the default system for nomenclature and identification in much of the world. The CASRN is increasingly the standard for unambiguous substance identification. The US EPA relies upon CAS to keep track of the TSCA inventory. Chemical sellers all over the world rely on the CASRN system to identify products and as a search term to attract internet search engines to their websites.

The major problem that I have encountered is that nomenclature from the 9th collective index (9CI) is often incompatible with our accounting system. The system does not accomodate Greek letters (kappa and eta) and the numbering system leads to sorting and format problems with list generation and subsequent retrieval. The complex system of numbering schemes and nested hierarchies plays havoc with the system as well, if for no other reason than the character count exceeds what is permissable in the data field.

Even more troublesome, the complex names are largely inaccessable to non-chemists. It is very hard for administrative assistants and temps to comprehend accounting data when they are fundamentally unsure of what the identity of the product is and why various materials show up in the bill of materials. To non-technical folks on the business side, chemical names are often just a complicated character string that is prone to data entry errors.

I’ll have to admit that nomenclature from earlier indices (6CI to 8CI) is often more user friendly in this regard. So when it is time to choose a name, 9CI doesn’t always win. This is a propagation step in the retention of obsolete nomenclature and I am guilty as hell of keeping it going.

2 thoughts on “Bis, Tris, Tetrakis

  1. Uncle Al

    CAS systematic nomenclature of bridged polycyclic aliphatics (e.g., dodecahedrane, dicyclcopentadiene) requires the molecule’s heavy atom skeleton to be stretched out and laid flat with no intersecting bonds. Said flat graph is then crunched by the rules. It is proven that almost all connectivities can be laid flat with no bond overlaps (Kuratowski’s theorem). “Almost” is not quite100%.

    In January 2008 there were 33,565,050 organic and inorganic substances in the CAS registry. About eight of those are very, very naughty like this (unpublished) one,


    to which neither CAS nor IUPAC could assign a formal name. It can be done! It required a German specialist and three days by hand, followed by a revision of naming software. Uncle Al did it to annoy.

    (EVERY carbon atom is chiral, including the methylenes and the undistorted tetrahedral symmetrically-substituted carbon at the center: no inversion point, mirror plane of symmetry, or higher improper axis at any carbon atom or globally.)

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  2. David Spector

    I believe that no one-dimensional symbolic description language can express all possible 3-dimensional organic molecules. I don’t know enough mathematics to cite a theorem. Can anyone confirm?

    David

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