playing the violin is easy

From The need for good nomenclature by Edward W. Godly:

[T]he IUPAC ‘Blue Book’ rules are something of a patchwork quilt. It is intended to cover the entire bed of Organic Chemistry although some parts are covered more than once.

Even if a beautifully simple and appealing new system were devised and promulgated now, it would not result in immediate abandonment of existing procedures nor even a gradual supplanting of them. An attempt was made to re-think the whole approach to systematic nomenclature following the discernment by the author of a lack of logicality in the patchwork of revision and extension to organic nomenclature over the past 200 years. This is the so-called HIRN system, the principles for which were published in 1984. Its author claims it to be simple, logically consistent and to use far fewer rules than those of IUPAC. So far, it has not won many converts and this characterizes the general attitude to chemical nomenclature, even among chemists, i.e. almost total lack of interest.

The mid-century devising of line notations was seen as a liberation from all the complexity of systematic naming. Unfortunately, the Wiswesser Line Notation — the one which most widely caught on — requires mastery of a set of encoding and decoding rules filling well over 200 pages of an instruction manual. The system is easy to apply in the sense that playing the violin is easy; in other words the required facility is achieved only by constant practice.

It probably comes as a shock to discover that the rules do not constitute a beginner’s instruction manual but are couched in terse language and require months if not years of study and practice before a fairly complicated molecule can be tackled with confidence. A commonplace reaction is to riffle through the Blue Book looking for an example that looks fairly close to the molecule in question and try to name it by analogy.

I tried to meet certain aspects of this demand by writing a stand-alone instruction manual on naming new organic compounds. <...> Initial trials on user panels gave promising results, the only failures being due to certain subjects inserting bits of their own knowledge instead of blindly following the instructions.

this is the extent of serendipity

According to Wikipedia, Charles J. Pedersen (1904—1989) “is one of the few people to win a Nobel Prize in the sciences without having a PhD”. Pedersen received the Nobel Prize in Chemistry in 1987, twenty years after he published his classic paper on crown ethers [1].

Revisiting his work for Current Contents^® (remember them?), he wrote [2]:

In 1961, at age 57, I began to study the effects of uni- and multidentate phenolic ligands on the catalytic properties of the VO group. The desired ligands, up to and including the quadridentate, had been synthesized. Now, the quinquedentate ligand, bis[2-(o-hydroxyphenoxy)ethyl] ether, was to be prepared by reacting a catechol derivative containing a protected hydroxyl (contaminafed with 10 percent catechol) with bis(2-chloroethyl) ether. The expected quinquedentate ligand was obtained, but nature lent a hand to provide the hexadentate dibenzo-18-crown-6 in 0.4 percent yield. This is the extent of serendipity.

Other crown ethers were synthesized, and when their unique properties had been determined, an exhilarating period of research was inaugurated: every successful experiment produced a significantly novel result.

The crown ethers might have been stillborn in another environment. They were discovered in the Elastomer Chemicals Department of E. I. du Pont de Nemours and Company, but what had they to do with elastomets? Moreover, the small amount of the byproduct might have been tossed out or disregarded as something other than the desired product. However, with the support of the top departmental management (C.J. Harrington, A.S. Carter, H.E. Schroeder, and R. Pariser), I worked independently with these compounds for nearly eight years. During the period leading to the paper, my sole coworker was T.T. Malinowski, a laboratory technician. I also had the resources of the analytical groups and the chance to consult with anyone on the technical staff of the company.

The editor of the Journal of the American Chemical Society, Gates Marshall, wrote of the manuscript: “You are clearly reporting a monumental piece of work...” But he complained that the experimental section “...looked as though it had been copied verbatim from a laboratory notebook.” He contributed to the frequency of citation by allowing two unusual features in the paper: length (20 pages) and a new system of nomenclature (crown) for identifying compounds whose official names boggle the mind.

I don’t know about you but I find all this astounding. A guy sans Ph.D. is allowed to work for eight years on something that has nothing to do with his company’s products. Two years before his retirement, he publishes a single-author experimental paper on synthesis and characterisation of 33 cyclic polyethers, plus proposes the new nomenclature system for crown ethers that we still use today. It is as if the management knew he’s gonna win the Nobel and just let him work toward it.

References

1. Pedersen, C.J. (1967) Cyclic polyethers and their complexes with metal salts. Journal of the American Chemical Society 89, 7017—7036.
2. Pedersen, C.J. This Week’s Citation Classic. Current Contents^®, no. 32, August 12, 1985, p. 18.