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Robinson, Robert

ROBINSON, ROBERT

(b. Rufford Farm [near Chesterfield], Derbyshire, United Kingdom, 13 September 1886; d. London, United Kingdom, 8 February 1975), chemistry, electronic theory, natural products, synthesis, structure.

Robinson was one of the greatest organic chemists of the twentieth century. His outstanding achievements led to both a Nobel Prize and an Order of Merit, particularly for his work on the synthesis and structure of natural products, including alkaloids and plant pigments. He was also one of the founders of the electronic theory of organic chemistry.

Early Years Robert Robinson was born on 13 September 1886 at Rufford Farm, near Chesterfield in Derbyshire, a thriving market town of great antiquity. His parents were William Bradbury Robinson and William’s second wife, Jane Davenport. There had been ten children from William’s first marriage, and Robert was the eldest of five by the second wife. The father was an inventive manufacturer whose innovations included the mechanization of cardboard box production and automation in the manufacture of surgical dressings, the latter being the family firm’s chief concern.

When Robert was three years old, the family moved to another town near Chesterfield, where he began his education. After attending a kindergarten school he went to Chesterfield Grammar School, whose headmaster seems to have been the first to stimulate his interest in mathematics. Although a weekly boarder, he spent plenty of time at home, and there developed three interests that remained with him for life. One was a general interest in natural phenomena, for the countryside was almost on his doorstep. The second arose from the excursions he often made from home to the hilly country around, not least some rocky outcrops that he climbed with ease and which generated a love for mountains that never left him. The third interest was chess, which he learned from the various Congregational ministers who regularly visited his parents. (They belonged at that time to Brampton Congregational Church.) He did not, however, share their faith and apparently remained a skeptic throughout his life.

At the age of twelve Robert was sent to Fulneck School, near Leeds in West Yorkshire, again as a boarder. The school had been recommended by several people and had a good academic reputation. It was a coeducational establishment run by the Moravians, situated in an area of great natural charm. The years passed fairly uneventfully, and Robert’s interest in mathematics was deepened by individual tutoring in his last year from J. H. Blandford, a Cambridge University mathematician on the staff. By this time, at the dawn of the twentieth century, it was not uncommon for comparatively affluent fathers to send their sons to a university, and in Robert’s case this seems to have been settled quite early. Robert, however, wanted to study mathematics, but his father saw value in another subject, one that would be more useful to industry, his own in particular. Robert had already won a gold sovereign from his father for designing an automatic lint-cutting machine, thus showing considerable practical inventiveness. Such a flair would be enhanced by scientific knowledge. This had to be in chemistry, for industries using textiles had for long been indebted to chemists for many processes, such as scouring, bleaching, mordanting, dyeing, and testing. Indeed, William Robinson had tried, albeit unsuccessfully, to build a bleachworks on the basis of an encyclopedia article. So chemistry was the choice of subject, the university was Manchester, and there Robert went in 1902.

Manchester The chemistry department at Manchester was at that time internationally renowned. From the days of Edward Frankland, its first professor, and those of his successor, Henry E. Roscoe, the department had flourished, and at Robinson’s arrival it was led by Harold Baily Dixon, famous for his research on explosives and on “dry reactions.” The professor of organic chemistry was William H. Perkin Jr. (son of the legendary William H. Perkin, who discovered mauve dye), then at the height of his powers. The two professors were effective lecturers, though it was Perkin who inspired Robert with a lifelong devotion to the chemistry of carbon. His third year included (appropriately enough) special practical work in the chemistry of dyestuffs, directed by Jocelyn Field Thorpe. An interesting comment on his work comes in a laboratory record of 1902: “Robinson, Robert—a good worker but messy.” However, he graduated with first class honors in 1905.

Robinson’s undergraduate days at Manchester were enlivened by hill walking, cricket, and attendance at the Music Hall, theaters, and operas. Fellow students who later blossomed in chemistry included John Lionel Simonsen and Walter Norman Haworth. At home, vacations offered an opportunity to continue chemical experiments in a small laboratory specially built by his father. One achievement here was a synthesis of terebic acid by the recently discovered Grignard reaction, his first original work in organic synthesis.

Upon graduation Robinson was invited to work in Perkin’s private laboratory. After some initial work on the preparation of ethyl piperonylacetate, he was diverted into a study of the natural dyestuff bRāzīlin, a constituent of bRāzīlwood and for some time an interest of Perkin himself. Robinson doubted some of Perkin’s conclusions, mainly because bRāzīlinic acid obtained by permanganate oxidation of trimethylbRāzīlin was assumed to contain -CH2– groups, rarely found after such oxidations. With Perkin’s encouragement he entered the field of bRāzīlin chemistry. A complex molecule, it did not yield up its secrets immediately, and Robinson’s last paper on the subject was published in 1974, sixty-eight years after his first. Unhappy with Perkin’s tentative structure, he proposed an alternative that later proved to be correct. He went on to examine a number of other natural products with a view to determining their structures. They included hematoxylin and the alkaloids berberine, harmaline, harmine, and strychnine. This last compound fascinated Robinson till the end of his life. This was no doubt partly because of its notoriety as a poison, but also because its structure resisted elucidation till the 1940s. By 1910 his papers had become sufficiently numerous and useful to earn him the degree of DSc. Shortly after this he became residential tutor in chemistry at Dalton Hall, one of the university’s halls of residence.

During his Manchester years Robinson made many friends in the department, one of whom was Arthur Lap-worth, newly arrived in 1909. Trained at the Central Technical College in London, where Henry Edward Armstrong was the professor, he became head of chemistry at Goldsmith’s College (owned by the University of London, but not part of it). They shared many interests, including music (Robinson played the piano, Lapworth the violin), identification of wildflowers, walking, and climbing. However, it was Lapworth’s ideas on chemical polarity that proved the most important link, and they led directly to Robinson’s own speculations on reaction mechanisms.

Another acquaintance in the department was Gertrude Walsh, a young woman student from Cheshire. She and Robert were attracted to each other, and both loved mountains as well as chemistry. They married at Over Parish Church, Cheshire, on 7 August 1912. Shortly after this, life was to take a dramatic new turn as the Robinsons sailed to Australia, where Robert had been appointed to a newly created chair of pure and applied organic chemistry at the University of Sydney. Such a move overseas was by no means unusual for English chemists at that time. He went with Perkin’s full support and encouragement and the prospect of a much larger salary, but also for another reason. He himself confessed: “I applied for the post in Sydney, in the first instance, because it would be an excellent base for the exploration of the alpine chain of the New Zealand Alps. This was my primary objective, not, I am afraid at that stage, the advancement of the science of chemistry” (Robinson, 1976, p. 81)

Sydney, Australia Despite the considerable distance of New Zealand from Australia, the Robinsons managed several trips: “all possible [university] vacations, up to three months at a time,” he claimed. They ascended such mountains as Coronet Peak and nearby Mount Neeson in the Southern Alps and Mount Egmont in North Island. He and Gertrude had a full social life in Sydney, she being also a demonstrator in his department. In 1914 the Robinsons had their first child, a daughter who sadly survived for only one day.

During the term there were lectures to give, and Robinson found some difficulty in addressing—and even controlling—classes of medical students and others who were studying chemistry merely because of university regulations. His lectures to aspiring chemists, on the other hand, were well-received, even though they seem to have been largely impromptu romps through the part of the subject that really interested him.

Among the research undertaken at Sydney were studies of C-alkylations of enolates, synthesis of various derivatives of catechol, and an investigation into eudesmin, a component of the oil from the Australian eucalyptus tree. He continued to write up his work from Manchester days and was much encouraged by a visit to Australia by the British Association for the Advancement of Science in 1914. Here he met Nevil V. Sidgwick, H. E. Armstrong, and other British chemists. It turned out that each of these was to give valuable support to an application Robinson was about to make to the University of Liverpool for a chair in organic chemistry. Despite being the youngest candidate at the age of twenty-nine, he was appointed, and after a long and leisurely cruise via the United States, the Robinsons returned to Britain with World War I well underway.

Liverpool Robinson took up his duties at Liverpool in January 1916. He continued his research on alkaloids and other natural products but by now was beginning to focus on the mechanisms by which such substances are created in nature. He also gave courses of lectures and, as before, used illustrations from his own ongoing research. The Robinsons settled in a house in Warrington, where gardening became a lifelong interest. However, life at that time was overshadowed by the war, and the Liverpool chemists were expected to contribute. The effective head of the department, Edward C. C. Baly, organized attempts to manufacture chemicals vital to the war effort. These included TNT and picric acid, both of which were to receive attention from Robinson. His natural products researches concentrated on the synthesis of alkaloids, then in short supply. Tropinone, a relative of atropine and cocaine, was successfully produced. For some time it had been supposed that tropinone was the first stage in the biosynthesis of both these alkaloids. Robinson’s achievement was to discover a very simple synthesis at room temperature, using succindialdehyde, methylamine, and an ester or salt of acetonedicarboxylic acid. Later work concerned the isoquinoline group of alkaloids that include morphine and odeine. He was concerned to ascertain their structural relationships and so to account for their biogenesis. In the ensuing years this work was continued by himself and others, including Richard Wilstätter, Alan Battersby, and Derek H. R. Barton, and was the subject of several major lectures, including his presidential address to the Royal Society in 1947.

Of great long-term importance for Robinson was the Advisory Board set up in 1917 to promote collaboration between academia and industry in northern England, much needed for the development of national resources at that time. It consisted of Baly; Robinson; five other departmental colleagues; and representatives of the local chemical industry, including Brunner Mond, CastnerKellner Alkali Co., Salt Union, and United Alkali. Another firm was Joseph Crosfield & Co., soap makers in Warrington whose managing director was Edward F. Armstrong, the son of H. E. Armstrong. On their behalf Robinson discovered a new synthesis of octanol, a contribution to Armstrong’s program of large-scale catalytic synthesis of simple organic chemicals used in his industry, especially detergents Other industrial contacts included visits to the home of Edmund K. Muspratt, son of James Muspratt, founder of the British alkali industry. An early consultancy project for Robinson was connected to the fact that oil was burning in Liverpool harbor. Robinson established that the problem lay in a combination of oil and floating driftwood. When asked about his fee, he suggested that the harbor authorities give a donation to the university library. He ruefully reported this was the first and last time he was foolish enough to decline a personal fee. Meanwhile, a government-backed company called British Dyes had been established, mainly to protect the industry from a possible revival of its German counterpart. In the absence of many qualified staff the firm approached Perkin, who established small groups of workers in a few university departments, among them Liverpool. Robinson was drawn into this arrangement in 1916, but little seems to have been achieved. In 1919 British Dyes and the rival firm of Levinstein merged to become the British Dyestuffs Corporation (BDC). Robinson resigned his chair and, in January 1920, commenced employment as director of research for BDC at its works in Huddersfield.

Huddersfield To his colleagues this seemed an astonishing move, initiated by a personal approach from Herbert Levinstein, one of the two new managing directors for the BDC. Robinson’s only recorded motive for the change appears to have been that it seemed to him to be “very much in the national interest” for British leadership in the postwar chemical industry, because British firms might well face a threat from German rivals. Patriotism apart, it seems that the new post carried a good salary and conditions.

Not far from the works in Huddersfield, the Robinsons settled in a house where, in 1921, their daughter Marion was born. She became a medical missionary and in 1960 married Mark Way, the bishop of Masasi, Tanganykia (later Tanzania). Robinson had a Liverpool graduate, Wilfred Lawson, to assist him in the laboratory, and their experiments on the azo-dyes led to new products, particularly those derived from coupling diazonium salts with cresols. He gained thereby a deeper insight into the industrial aspects of dyestuffs chemistry. He was elected a Fellow of the Royal Society in 1920 and elected to the council of the Chemical Society in 1921.

However, the years at Huddersfield were marred by fierce antagonism between the two managers, Levinstein and Joseph Turner, and by the existence within the works of a technical chemistry laboratory whose collaboration with Robinson’s was minimal. Accordingly, he sought a return to academic life, and when the opportunity arose in 1921, Robinson seized it. The chair of chemistry at St. Andrews had just been vacated by James C. Irvine on his appointment as principal. Robinson successfully applied for the post, and late in 1921 the family moved to Scotland.

St. Andrews Although at St. Andrews for only a year, the Robinsons enjoyed their new circumstances. Gertrude registered as a research student and Marion began to attend infant school. The opportunities for mountaineering in the Highlands were obvious, and the laboratory occupied by Robert had a spectacular view of the North Sea. In fact, he was able to work in a relatively new laboratory in the oldest university in Scotland (founded in 1410). He did not, however, continue in the carbohydrate tradition inherited from Irvine and his predecessor, Thomas Purdie. That tradition was continued elsewhere, particularly by Walter N. Haworth and by Edmund Langley Hirst, who had been associated with Irvine at St. Andrews before Robinson’s time. However, Robinson did suggest to Hirst that the received wisdom that carbohydrates had stable 5-membered rings (like lactones) might be incorrect and that they might instead have 6-membered rings. This speculation was remembered by Hirst, who some years later proved it to be correct.

Robinson continued his work on alkaloids and (with John Mason Gulland) confirmed a new structure for the morphine family.

Robinson’s sojourn in St. Andrews was brought to a sharp and unexpected termination by events in Manchester. There, the senior professorship was made vacant by H.

B. Dixon’s retirement; this was expected, but surprise was occasioned by the elevation to that chair of Arthur Lapworth from his professorship of organic chemistry. Lapworth’s chair, therefore, had to be filled; Robinson was approached, made formal application, and was accepted without competition. It is likely that Lapworth’s own move, and the subsequent invitation to Robinson, was a deliberate attempt to renew collaboration of the kind they had enjoyed many years earlier. In any event, the move back to Manchester in 1922 proved to be of great importance to chemistry.

Manchester, Again Now only thirty-six years old but having already occupied two university chairs, Robinson was able to attract many promising workers to his laboratory. Gulland and David Doig Pratt came with him from St. Andrews, the latter continuing work begun on a group of plant pigments known as the anthocyanins, which are responsible for most of the reds and blues in flowers. This work was also followed by Alexander J. Robertson, who was with Robinson from 1924 to 1928. Robinson also collaborated with Arthur George Perkin of the University of Leeds on carajura, a plant material from Venezuela, and with Frank Lee Pyman of the Boots Drug Co. on anti-malarials. Among his research students were Tiruvenkata Rajendra Seshadri (who deduced the structure of carajurin, a derivative of carajura) and W. Bradley (who worked on diazo-ketones and anthocyanin synthesis). From 1925 Robinson also worked with his wife, Gertrude, on the synthesis of fatty acids.

Most notable of all his collaborations must surely be his work with Lapworth, whose strong interest in reaction mechanisms had already greatly impressed Robinson in his first Manchester period. Now direct cooperation became a daily possibility, with the two men often seen closeted together at lunch, covering old envelopes with symbols from the new electronic theory that they were developing. Together with James Wilson Armit, he published an idea that was conceived in St. Andrews, a proposal for the electronic structure of benzene. In place of the familiar Kekulé formula with alternating double and single bonds in the ring, he suggested in 1925 that the six “spare” electrons not needed for the three associated with each carbon atom should be regarded as a stable, nonlocalized group. This confers a special kind of stability on the molecule. Since it occurs only in aromatic substances, he called it the “aromatic sextet,” which is applicable to such other systems as pyridine and pyrrole (but not to pyrrole salts, where the electron pair associated with the nitrogen atom is no longer available). This concept proved of great importance in later years and prefigured the use of molecular orbitals.

Also in 1925, Robinson and three coauthors presented a paper about the directive effects of substituents on the course of aromatic substitution. Shortly after this, unfortunately, an acrimonious disagreement arose with Christopher K. Ingold regarding details of the electronic theory. Controversy raged at Chemical Society meetings and elsewhere, and “the absurd game of noughts and crosses [tic tac toe]” was ridiculed by H. E. Armstrong. Robinson remained convinced he was right but soon lost interest in the electronic theory and returned to his first love: natural products. Robinson remarked later in life that he thought his work on the electronic theory was his most important contribution to chemistry. He also believed that Ingold had appropriated his ideas without giving due credit. However, subsequent research has shown the issues were far from simple and the rather distasteful dispute shows neither participant in a very good light.

Robinson came back to the subject in 1932 to deliver two lectures, subsequently published. Also, in 1946 Robinson intended to collaborate with Michael J. S. Dewar on a much larger exposition; in the event, he wrote the foreword to the latter’s important Electronic Theory of Organic Chemistry (1949).

University College, London In 1928 Robinson moved yet again after he was invited to become professor of organic chemistry at University College, London. His motives for acceptance are obscure. The family had been unsettled by the birth of a son, Michael, in 1926, who was found to suffer from Down syndrome, and possibly this spurred Robinson to welcome a new sphere of work. After characteristically spending five weeks’ holiday in the Alps, the Robinsons settled into a new home in Hendon. Gertrude became known as a generous hostess and Robert drove to the college. Among his friends was Frederick G. Donnan (once a colleague at Liverpool) and his predecessor, J. Norman Collie, who continued as emeritus professor. Like Robinson, Collie delighted in mountains, and they shared many climbing experiences on the Island of Skye, one of whose peaks (Sgurr Thormaid, or Norman’s Peak, [926 m., or 3,038 ft., high]) was named after Collie. Robinson’s industrial interests were kept alive by a series of consultancy appointments, particularly to Imperial Chemical Industries (ICI) in 1927.

Robinson continued researches from earlier periods, including anthocyanin synthesis and determination of the structure of bRāzīlin. However, he had hardly been in his

post for a year when, in 1929, his former mentor, W. H. Perkin, died, and his prestigious post at Oxford became vacant. Robinson applied and was soon appointed, though he was not free to leave University College until the following July. Thereafter, he became Waynflete Professor of Chemistry at Oxford, and also head of the Dyson Perrins Laboratory. By a strange irony, his successor at University College was C. K. Ingold.

Oxford Robinson inherited Perkin’s new Dyson Perrins Laboratory, and here he remained for twenty-five years: his wanderings were over. He brought with him about twenty associates from University College and continued to supervise their work. However, he gradually became less involved in working at the laboratory bench and tended to withdraw from the departmental activities. Nor was Robinson greatly interested in the business of his college, Magdalen, and he appears to have made few friends in Oxford during his long stay. One reason was undoubtedly the increase in his outside interests. Robinson continued an enthusiastic gardener, chess player, and mountaineer, and he also engaged in foreign travel to deliver lectures or attend meetings. Much of his time, however, was devoted to deep thought about the chemistry of the natural products studied in his laboratory. He tended to avoid detailed experimental work but supervised his research students, who did most of the bench-work. Slightly erratic in his supervision, he gave most attention to the topics that were uppermost in his mind at the time. From 1930 to 1934, colleagues included Bertrie Kennedy Blount and Alexander Todd. His work on plant pigments was drawing to a close, though he still shared his wife’s interest in the genetics of color variation in flowers. From the 1930s onward, he concentrated on sterols. This led to, among much else, an industrial synthesis of the female hormone diethylstilbestrol, used for some time in treating prostate cancer. He continued his association with ICI and Boots and joined a research committee set up by Anglo-Persian Oil concerned with the development of a high-octane motor fuel.

By this time Robinson’s work was internationally recognized. In 1939 he received a knighthood and became president of the Chemical Society. Six years later he became president of the Royal Society.

With the advent of World War II, Robinson worked on topics of national importance such as chemotherapy and chemical defense, but eventually he concentrated on penicillin studies. Robinson had a well-known dispute with Robert Burns Woodward about the structure of penicillin, with Woodward eventually shown to be correct. This incident is significant because Robinson refused to give much credence to spectroscopic data, while Woodward was a pioneer in using it for organic structure determination. It displays the generational gap between two of the greatest synthetic organic chemists of the twentieth century, and the shift that was taking place at midcentury. Hostilities over, he returned to alkaloid studies (especially brucine and strychnine), and it is these that were named in the citation for his Nobel Prize in Chemistry in 1947. Further distinction came in 1949 with the award of the Order of Merit. He was able to postpone his retirement for four years beyond 1951. He then became president of the British Association for the Advancement of Science in 1955 and a director of Shell Chemical Co., with a small laboratory at Egham, in Surrey, starting that same year.

In 1954 Gertrude Robinson died suddenly. Three years later Robinson married Stearn Hillstrom. He continued to enjoy his lifelong interests of music and chess and climbed his last mountain in 1966. His closing years were marred by failing eyesight, and he became almost completely blind. Nevertheless, his intellect remained active, and he began an autobiography when he was age eighty-five, working at it on the day he died, 8 February 1975.

BIBLIOGRAPHY

Archival material for Robinson is scattered, important collections being at the Royal Society, the Bodleian Library at Oxford, and the Derbyshire County Record Office.

WORKS BY ROBINSON

Outline of an Electrochemical (Electronic) Theory of the Course of

Chemical Reactions. London: Royal Institute of Chemistry, 1932.

With E. David Morgan. An Introduction to Organic Chemistry.

London: Hutchinson, 1975.

Memoirs of a Minor Prophet: 70 Years of Organic Chemistry. New

York; Amsterdam, Netherlands: Elsevier, 1976. This was the first and only volume of his autobiography; more had been projected.

OTHER SOURCES

Dewar, Michael James Steuart. The Electronic Theory of Organic

Chemistry. Oxford: Clarendon Press, 1949. Robinson wrote the foreword.

Eilks, Ingo, and J. Friedrich. “Die Theorie der

Reaktionsmechanismen: Ingold oder Robinson?” Praxis Naturwissenschaft, Chemie 48 (1999): 29–33. “Robert Robinson Issue.” Natural Product Reports 4, no. 1

(1987). Includes articles by Edward P. Abraham, Kenneth W. Bentley, John Cornforth, Robert Livingstone, Colin Russell, Martin D. Saltzman, John Shorter, and Alexander R. Todd. Saltzman, Martin D. “Sir Robert Robinson—A Centennial

Tribute.” Chemistry in Britain 22 (1986): 543–548.

Slater, L. B. “Woodward, Robinson, and Strychnine: Chemical Structure and Chemists’ Challenge.” Ambix 48 (2001): 161–189.

Todd, Alexander R. “Sir Robert Robinson, 1886–1975.”

Chemistry in Britain 11 (1975): 296.

Todd, Alexander R., and John Cornforth. “Robert Robinson 13

September 1886–8 February 1975.” Biographical Memoirs of Fellows of the Royal Society 22 (1976): 415–527.

Williams, Trevor I. Robert Robinson: Chemist Extraordinary.

Oxford: Clarendon Press, 1990.

———. “Robert Robinson.” In Dictionary of National

Biography, edited by Brian Harrison. Oxford and New York: Oxford University Press, 2000.

Colin A. Russell

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Robinson, Robert

Robinson, Robert


ENGLISH ORGANIC CHEMIST
18861975

An acknowledged giant of twentieth-century organic chemistry, Robert Robinson authored 700 research papers that continue to influence the way organic chemists think about synthesis , natural products, and reaction mechanisms. He received many awards during his sixty-year career, including the 1947 Nobel Prize in chemistry "for his investigations on plant products of biological importance, especially the alkaloids."

Robinson was born on September 13, 1886, near Chesterfield, England. His father owned a surgical dressing factory and invented many of the machines used to produce and package such dressings. In high school Robinson excelled in mathematics and physics and hoped to become a mathematician. However, his father encouraged him to study chemistry instead, so Robinson accepted the inevitable and entered the chemistry program at the University of Manchester.

Robinson received his D.Sc. from Manchester in 1910 and lectured there for two additional years. He then accepted successive academic appointments at Sydney, Liverpool, Manchester, London, and finally Oxford University.

Today chemists use computer-driven instruments to determine the structures of unknown organic compounds. In Robinson's era, however, chemists relied less on instruments and more on degrading the compound into smaller, less complex fragments and then piecing them back together again. Using these techniques, Robinson determined the structures of complex alkaloids and worked on the antibiotic penicillin during World War II. His work on the structure of strychnine (see Figure 1) is still regarded as an outstanding example of molecular puzzle solving.

After structure comes synthesis, and modern chemists synthesize complex medicines and other important compounds using ideas originated by Robinson. But organic synthesis was in its infancy when Robinson started out, and in his stunning synthesis of tropinone (a compound related to cocaine) in 1917, he introduced a novel strategy for preparing complex organic compounds. On paper, Robinson disconnected, or broke, certain bonds in tropinone and arrived at three simpler building blocks. He then went to the laboratory, where he combined the three building blocks using

standard procedures and produced tropinone. This process is now called retrograde synthesis.

Because Robinson wanted to take a systematic approach to organic synthesis, he developed a set of theoretical tools to predict the outcomes of organic reactions. Many important drugs and natural products contain substituted benzene rings, so Robinson began his research by trying to predict the outcomes of substitution reactions in benzene derivatives. He and his wife, Gertrude, successfully explained one class of substitution reactions in a 1917 paper but were unable to provide a general theory.

Using ideas developed in Arthur Lapworth's 1922 paper, Robinson devised a new theory in 1924 that explained the chemistry of unsaturated systems such as benzene and 1,4-butadiene (a four-carbon chain with alternating double bonds). Using his new theory, Robinson successfully predicted the outcomes of chemical reactions in these unsaturated systems. And for the first time ever, he used curly arrows to show the distribution of electrons in conjugated systems and to predict substitution reactions in benzene analogs. Hardly a day goes by when a modern organic chemist does not use curly arrows to explain a reaction mechanism or to plan a synthetic route.

Although Robinson considered the curly arrow concept his most important contribution to knowledge, few chemists know he invented it. Most chemists attribute the discovery to Christopher Ingold. Ingold embraced Robinson's ideas and over time published so many of his own related papers that chemists tended to overlook Robinson's groundbreaking work. Robinson never forgave Ingold for taking credit for his ideas.

Robinson retired from Oxford in 1955 but remained active in the field of chemistry. In his younger days he climbed the Alps, Pyrenees, and major mountains in New Zealand and Norway. Chess was another of his passions: Robinson spent three years as president of the British Chess Federation. He died on February 8, 1975.

see also Organic Chemistry.

Thomas M. Zydowsky

Bibliography

James, Laylin K., ed. (1993). Nobel Laureates in Chemistry 19011992. Washington, DC: American Chemical Society; Chemical Heritage Foundation.

Internet Resources

"The Nobel Prize in Chemistry 1947." Nobel e-Museum. Available from <http://www.nobel.se/chemistry/laureates>.

"Robert RobinsonBiography." Nobel e-Museum. Available from <http://www.nobel.se/chemistry/laureates>.

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