The Nobel Prize in Chemistry 1987

Donald J. Cram

Professor Emeritus; BS, Rollins College; MS, University of Nebraska; Research Chemist, Merck & Co.; PhD, Harvard University; National Academy of Sciences; ACS Award for Creative Work in Synthetic Organic Chemistry; American Academy of Arts and Sciences; ACS Cope Award for Distinguished Achievement in Organic Chemistry; California Scientist of the Year Award; Honorary Doctor of Science degrees from Uppsala University, Sweden, the University of Southern California, Rollins College, the University of Nebraska, the University of Western Ontario, Canada, and the University of Sheffield, England; Southern California ACS R.C. Tolman Award; Chicago Section ACS Gibbs Medal; first holder of Saul Winstein Chair in Organic Chemistry; ACS Roger Adams Award; Nobel Prize; University Professor; Glenn T. Seaborg Award; National Academy of Sciences Award in Chemical Sciences; President, National Medical Sciences.

Research Description

Inspired by the model of evolutionary biological systems, the Cram research group is engaged in investigating host-guest complexation chemistry. Host multiheteromacrocycles with convergent binding sites embedded in concave surfaces converge on the binding sites of complementary guest compounds with divergent binding sites composing or attached to convex surfaces.

Binding forces are the sum of many host-guest contacts involving van der Waals attractions, hydrogen bonding, dipole-dipole attractions, ion-pairing, ligand to metal ion attractions, and solvophobic interactions. Structural recognition (including chiral recognition) in binding is applied to separations of enantiomers, to analyzing for Li[+], Na[+], and K[+] in serum, and to separation science and catalysis. Highly preorganized hosts (spherands, cavitands, and carcerands) are designed and synthesized. Correlations between structure and binding, structure and physical properties, structure and catalytic properties, and structure and separation are sought. Crystal structures are correlated with solutions structures using NMR spectra. Elaborate syntheses (up to 30 steps) are conducted, followed by physical-organic measurements.

The reactions of guest molecules imprisoned in the interior of rigidly hollow spherical host molecules (carceplexes) are being actively pursued. Potential uses of carceplexes include drug and radiation delivery systems, light switches, or molecular information storage and retrieval display systems (MISARDS). Guests, such as cyclobutadiene which ordinarily self-destructs, are stable when contained inside the shell of a carcerand.

Benzyne has been synthesized and studied in the inner phase of a carcerand.

The beginning is distant, and was a time when we as a people were without much of the fruits of science that now refine our lives. But it was also a good time, when family and town were the domain of our existence. My father of Scottish, and mother of German extraction, migrated with their three children from Ontario, Canada, to rural Chester, Vermont, USA, where I was born in the spring of 1919, as the Cram's fourth and only male child. Two years later, the family moved to Brattleboro, Vermont.

My mother, Joanna, was high-spirited throughout her 94 years, starting with a girlhood rebellion against the strict Mennonite faith in which she was raised. My father, William, was a romantic, a cavalry officer, later working alternately as a successful lawyer and unsuccessful farmer. He died of pneumonia at 53, leaving my mother with a set of Victorian upper-class English values, and the task of providing for and raising my sisters and me, then aged four.

According to my oldest sister, Elizabeth, I was as a child precocious, curious, and constantly in, or causing, trouble. This character trait started at birth; I weighed over ten pounds, and had an unusually large head! Determined to walk at seven months, I pulled a pan of fresh eggs down from a table onto that head. At three years, I broke my first window. My father took me directly to our neighbor, Mr. Mason, to apologize. Reputedly, I said to him, "Sorry, you nasty Mason".

By the time I was four and a half, I was reading children's books. My mother, steeped in English literature, cultivated incentive by reading to me only the beginnings of tales that involved heroes, heroines, hypocrites, and villains. When we reached the exciting part, she left me with the story to finish by myself. My childhood was adventuresome and idyllic in the things that mattered.

Elementary schooling for me was series of multiclass single-room buildings, where the young and very young witnessed each other being taught. On report card days, I faced searching questions and criticism during which "character grades" were stressed over academic accomplishments. I usually was marked "A" in attitude and accomplishment, "B" in effort, and "C" in obedience.

What I call my real education occurred principally outside of the classroom, in a private world of books and brooks. All of Dickens, Kipling, Scott, Shaw, and much of Shakespeare were read. I learned how to run up spring-fed brooks, jumping from one glacier-polished stone to another. I carried firewood, emptied ashes, and shoveled snow for music lessons. I picked apples to be paid in apples, strawberries to be paid in strawberries; and I moved the lawns of a large estate belonging to the dentist who filled my cavities and pulled my teeth.

The rate of exchange of my time for his was fifty to one. During the Christmas rush, I sold ties, shirts, shoes, gloves, and jackets in return for the same. By the time I was fourteen, my mother's barter arrangements were replaced by a flat fee of 15 cents an hour working for neighbors, raking leaves, hoeing corn, digging potatoes, pitching hay, and delivering newspapers. The last job taught me about debts, dogs, and bicycle bags.

At sixteen, I left my home in Brattleboro, Vermont, a handsome old town on the Connecticut River. By then I had learned how to adapt to eighteen different employers, and had played high school varsity tennis, football, and ice hockey. I also had my full growth of 195 pounds, and was 6 feet tall. My family dispersed at that time, and I drove two elderly ladies to Florida in a Model-A Ford, without benefit of a license, and in return for transportation. Stopping at Lake Worth, Florida, I worked in an ice-cream shop and weeded lawns in return for room and board. There, I continued my secondary schooling while suffering an acute case of homesickness for New England. Nine months later, I hitchhiked north again to Massachusetts, and passed the summer as a house painter and roofer. My twelfth grade was spent at Winwood, a little private school on Long Island, New York, working as a factotum for my tuition and board. While there, I did three things significant to my future. I took a course in chemistry, taught myself solid geometry from a book, and won a $6,000 four-year National Rollins College Honor Scholarship.

While at Rollins, in the resort town of Winter Park, Florida, I worked at chemistry and played at philosophy (four courses!). I read Dostoevski, Spengler, and Tolstoy, and sang in the choir and in a barbershop quartet. In four halcyon years, I obtained an airplane pilot's license, acted in plays, produced-announced a minor radio program, and, while my fellow students complained, dined on the best food I had yet encountered.

During the summers of 1938 to 1941, I worked for the National Biscuit Company in New York City, at first as a salesman covering an area from 144th Street to 78th Street on the tough East Side. The largest city in the country was also its best teacher. This was my first exposure to ghetto slums, youth gang warfare, drugs, prostitution, and petty thievery. The northern end of my territory was dominated by Jewish delicatessens, out of which at first (but not later) I was urged to leave. I got to know everybody, and everybody's business. In the Irish-run grocery stores, we would conduct "wakes" for the last fig bar in the bin. Harlem was a place where each street was a playground, and each store a small fort. The Puerto Rican district was full of street vendors of all sorts. I started that summer weighing 195 pounds, and ended it at 155. My $ 15 per week provided me with cash, and a crash course in ethnic groups and big city street-life. The other summers involved analyzing cheeses for moisture and fat content in the National Biscuit Laboratories.

From these routine jobs, I extracted pleasure by making them into games. They taught me self-discipline, and illustrated how I did not want to spend my life. But this period provided me with a keen interest in the differences between people, and an overwhelming dislike of repetitive activities. When the word "research" entered my vocabulary, it had a magic ring, suggesting the search for new phenomena. Chemical research became my god, and the conducting of it, my act of prayer, from 1938 to the present. When told by my first college chemistry professor, Dr. Guy Waddington, that he thought I would make a good industrial investigator - but probably not a good academic one - I determined upon an academic research career in chemistry.

Out of 17 applications for teaching assistantships to go to graduate school, three offers came. I accepted the University of Nebraska's, where an MS was granted in 1942. My thesis research there was done under the supervision of Dr. Norman O. Cromwell. By then, World War II was upon us, so I went to work for Merck & Co., ultimately on their penicillin project, where my search for excellence was symbolized by Dr. Max Tishler. Immediately after the war ended in 1945, Max arranged for me to attend Harvard University, working for Professor L.F. Fieser. The work for my Ph.D. degree on a National Research Council Fellowship was in hand in eighteen months.

At Harvard, scientific excellence was personified for me by Professors Paul D. Bartlett and Robert B. Woodward. After three months at M.I.T., working for Professor John D. Roberts, I set out for the University of California at Los Angeles on August 1, 1947, and have taught and researched there ever since, after 1985 as the S. Winstein Professor of Chemistry.

In retrospect, I judge that my father's death early in my life forced me to construct a model for my character composed of pieces taken from many different individuals, some being people I studied, and others lifted from books. The late Professor Saul Winstein, my colleague, friend, and competitor, contributed much to this model. It was almost complete by the time I was 35 years of age. Thus, through the early death of my father, I had an opportunity - indeed the necessity - to animate that father image that was slowly maturing in my mind's eye. And, at last, I realized who in fact this figure was. It was I.

The times and environment have been very good to me during my forty-six years of chemical research. I entered the profession at a period when physical, organic, and biochemistry were being integrated, when new spectroscopic windows on chemical structures were being opened, and when UCLA, a fine new university campus, was growing from a provincial to a world-class institution. My over 200 co-workers have shared with me the miseries of many failures and the pleasures of some triumphs. Their careers are my finest monument. My countrymen have supported our research without mandating its character. Jean Turner Cram, as my first wife, sacrificed for my career from 1940 to 1968. Dr. Jane Maxwell Cram, my second wife, acted as foil, unsparing but inspiring critic and research strategist in ways beyond mention.

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