Le Couteur: Napoleon's Buttons

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Penny Le Couteur and Jay Burreson, Napoleon's Buttons : How 17 Molecules Changed History. New York : Jeremy P. Tarcher/Putnam, 2003. 375 pages with selected bibliography; copiously illustrated with molecular diagrams and photographs.

I must confess that I started out with a condescending attitude about this book. "How 17 molecules changed history" sounded histrionic to me, so I was predisposed to find the text hyperbolic and the prose breezy, etc.

I couldn't have been more wrong. Napoleon's Buttons is charming and informative and lucidly written, but no light-weight for all that. Indeed, it takes an historic approach to telling fascinating stories about, as promised, molecular families that could lay claim to having altered history. They are also molecular families that readily teach general lessons about (predominantly) organic chemistry, a broad discipline of science that the average person would find daunting to approach. About the only stretch of poetic license was for the title: did Napoleon lose Russia because his soldiers' buttons were made of tin? (The hypothesis behind the question: that the Russian cold of winter caused the tin buttons to disintegrate, an affliction known as "tin pest", which left the soldiers holding their jackets shut rather than fighting.)

The table of contents gives clear warning of what's to be talked about

1. Peppers, Nutmeg, and Cloves
2. Ascorbic Acid
3. Glucose
4. Cellulose
5. Nitro Compounds
6. Silk and Nylon
7. Phenol
8. Isoprene
9. Dyes
10. Wonder Drugs
11. The Pill
12. Molecules of Witchcraft
13. Morphine, Nicotine, and Caffeine
14. Oleic Acid
15. Salt
16. Chlorocarbon Compounds
17. Molecules Versus Malaria

What that doesn't tell us is how much fun talking about them can be. The chapters are a nice blend of anecdote, analysis, and chemistry, complete with molecular diagrams. The diagrams might be scary to some readers, but they shouldn't be: they're fun to look at and along the way one starts to get a sense of the information the diagrams convey.

Some examples will give a nice flavor of the writing. First, from the chapter on ascorbic acid, demonstrating that even the best chemist are always the best at naming things:

In 1928, Albert Szent-Györgyi, a Hungarian doctor and biochemist working at Cambridge University in England, extracted less than a gram of crystalline material from bovine adrenal cortex, the inner fatty part of a pair of endocrine glands situated near a cow's kidneys. Present at only about 0.03 percent by weight in his source, the compound was not initially recognized as vitamin C. Szent-Györgyi thought he had isolated a new sugar-like hormone and suggested the name ignose, the ose part being the ending used for names of sugars (like glucose and fructose) and the ig part signifying that he was ignorant of the substance's structure. When Szent-Györgyi's second suggestion for a name, Godnose, was also rejected by the editor of the Biochemical Journal (who obviously did not share his sense of humor), he settled for the more sedate name hexuronic acid. Szent-Györgyi's sample had been pure enough for accurate chemical analysis to show six carbon atoms in the formula, C6H8O6, hence the hex of hexuronic acid. Four years later it was shown that hexuronic acid and vitamin C were, as Szent-Györgyi had come to suspect, one and the same. [pp. 47—48]

From the same chapter, here is the citation for ascorbic acid's claim to altering the course of history:

Even in the early twentieth century a few Antarctic explorers still supported theories that putrefaction of preserved food, acid intoxication of the blood, and bacterial infections were the cause of scurvy [rather than a deficiency in Vitamin C]. Despite the fact that compulsory lemon juice had virtually eliminated scurvy from the British navy in the early 1800s, despite observations that Eskimos in the polar regions who ate the vitamin C-rich fresh meat, brain, heart, and kidneys of seals never suffered from scurvy, and despite the experience of numerous explorers whose antiscorbutic precautions included as much fresh food as possible in the diet, the British naval commander Robert Falcon Scott persisted in his belief that scurvy was caused by tainted meat. The Norwegian explorer Roald Amundsen, on the other hand, took the threat of scurvy seriously and based the diet for his successful South Pole expedition on fresh seal and dog meat. His 1911 return journey to the pole, some fourteen hundred miles, was accomplished without sickness or accident. Scott's men were not so fortunate. Their return journey, after reaching the South Pole in January 1912, was slowed by what is now thought to be the Antarctic's worst weather in years. Symptoms of scurvy, brought on by several months on a diet devoid of fresh food and vitamin C, may have greatly hampered their efforts. Only eleven miles from a food and fuel depot they found themselves too exhausted to continue. For Commander Scott and his companions, just a few milligrams of ascorbic acid might have changed their world. [pp. 51—52]

From the chapter on cellulose, a demonstration of the authors' explanation of some everyday properties of cotton with some chemical insights:

Many of the traits that make cotton such a desirable fabric arise from the unique structure of cellulose. Long cellulose chains pack tightly together, forming the rigid, insoluble fiber of which plant cell walls are constructed. X-ray analysis and electron microscopy, techniques used to determine physical structures of substances, show that the cellulose chains lie side by side in bundles. The shape a beta linkage confers on the structure allows the cellulose chains to pack closely enough to form these bundles, which then twist together to form fibers visible to the naked eye. On the outside of the bundles are the OH groups that have not taken part in the formation of the long cellulose chain, and these OH groups can attract water molecules. Thus cellulose can take up water, accounting for the high absorbency of cotton and other cellulose-based products. The statement that "cotton breathes" has nothing to do with the passage of air but everything to do with the absorbency of water by cotton. In hot weather perspiration from the body is absorbed by cotton garments as it evaporates, cooling us down. Clothes made from nylon or polyester don't absorb moisture, so perspiration is not "wicked" away from the body, leading to an uncomfortable humid state. [p. 77]

Finally, a brief discussion of the discovery of "saponification", a most unlikely discovery: who would think that dropping fat into ashes would create a product that might clean things!

Roman legend attributes the discovery of soap making to women washing clothes in the Tiber River downstream from the temple on Mount Sapo. Fats from animals sacrificed at the temple combined with ashes from sacrificial fires. When it was raining, these wastes would rain down the hill and enter the Tiber as a soapy stream, which could be used by the washerwomen of Rome. The chemical term for the reaction that occurs when triglycerides of fats and oils react with alkalis—from ashes—is saponification, the word derived from the name of Mount Sapo, as is the word for soap in a number of languages. [p. 285]

I applaud the authors for not trying to dumb down their text and avoid chemical names and technical terms, because the language of chemistry is useful and carries a lot of its history with it. Fortunately, the authors set out to present their material for a general audience and use unfamiliar language as a tactic to enhance their presentation rather than confound the reader.

I think both general readers and the more technically inclined—even chemists!—will find plenty in this book to entertain and inform. I did.

-- Notes by JNS