The Reveries of Kekul

Taken from Eurekas and Euphorias: The Oxford Book of Scientific Anecdotes, by Walter Gratzer
August Kekul von Stradonitz was one of the founders of structural organic chemistry. Born in Darmstadt in 1829, he studied at the University of Giessen with Justus von Liebig, greatest of all organic chemists, then in France, and finally in England. He later took the chair of chemistry at the University of Ghent and then in 1865 he moved to Bonn, where he remained for the rest of his life. Kekul was a noted teacher, but is now mainly remembered for his celebrated dreams, in which came to him the two inspirations that changed the face of chemistry. It happened twice, the first time while he was in London. Kekul was living in lodgings in Clapham and was accustomed to spend frequent evenings with a friend, another German chemist, Hugo Mueller. They talked about chemistry and, most of all, the structure of molecules, Kekul's special preoccupation: how were the atoms arranged within the molecule, and how did it come about that two molecules with the same atomic composition - containing, suppose, 5 carbon atoms and 12 hydrogens - could be different substances? After one such congenial evening, Kekul caught the last bus home. It was a fine summer evening and he took his seat on the open top deck of the horse-drawn conveyance. Here is how, many years later, he described his experience: I fell into a reverie, and lo, the atoms were gambolling before my eyes. Whenever, hitherto, these diminutive beings had appeared to me, they had always been in motion. Now, however, I saw how, frequently, two smaller atoms united to form a pair; how a larger one embraced the two smaller ones; how still larger ones kept hold of three or even four of the smaller; whilst the whole kept whirling in a giddy dance. I saw how the larger ones formed a chain, dragging the smaller ones after them, but only at the ends of the chain. Kekul, roused by the conductor's cry of Clapham Road, returned to his room and spent the rest of the night sketching the formulae on which his theory of structure came to be based. It was known that carbon has a valency of four; each carbon atom, in other words, can attach itself to four other atoms in forming a compound. In the simple example given above, then, the molecule C5H12, pentane, exists in three forms, where CH3 and CH2 represent carbon atoms linked to three and to two hydrogen atoms:

H3C

H C

H2 C CH3

CH3

H2 C H3C C H2

H2 C CH3

H3C C

CH3

CH3

CH3

While in Ghent, Kekul experienced a similar epiphany. This time the object of his reverie was the molecule benzene, which has the composition C6H6. This is the archetype of the aromatic compounds, a class to which a large proportion of the most interesting synthetic and naturally occurring substances belong. Here again is Kekul's reminiscence: I was sitting writing on my textbook, but the work did not progress; my thoughts were elsewhere. I turned my chair to the fire and dozed. Again the atoms were gambolling before my eyes. This time the smaller groups kept modestly in the background. My mental eye, rendered more acute by repeated visions of the kind, could now distinguish larger structures of manifold conformation: long rows sometimes more closely fitted together all twining and twisting in snake-like motion. But look! What was that? One of the snakes had seized hold of its own tail, and the form whirled mockingly before my eyes. As if by a flash of lightening I awoke; and this time also I spent the rest of the night working out the consequences of the hypothesis. The hypothesis, of course, was that benzene was a cyclic molecule, the six carbon atoms forming a hexagon, one hydrogen attached at each corner. Adolf von Baeyer, the great organic chemist, said that he would have exchanged his lifetime's accomplishments for this one insight of Kekul's. It is no surprise that during the heyday of Freudian interpretation of dreams Kekul's vision of snakes was given a sexual connotation, for he was living in bachelor quarters, far removed from his wife, whom he would have seen rather seldom. But then there is little that has not at some time been interpreted in such terms. See, for example, 0. T. Benfey, Journal of Chemical Education, 35, 21 (1958).