Collie, John Norman

Collie, John Norman

(b. Alderley Edge, Cheshire, England, 10 September 1859; d. Sligachan, Isle of Skye, Scotland, 1 November 1942),

chemistry.

The second son of John and Selina Mary Collie, John Norman learned early in life to love the outdoors so much that mountaineering vied with chemistry as his chief interest in life. In 1877 he entered University College, Bristol, where he studied under E. A. Letts. Collie continued his studies as assistant to Letts when the latter moved to Queen’s College, Belfast, in 1879, working on reactions of tetrabenzyl phosphonium salts. In 1883 Collie went to Wurzburg to obtain his Ph.D.under Wislicenus, studying thermal decomposition products of phosphonium and ammonium salts. Here Collie also began the study of β-aminocrotonic ester that led him ultimately into his major works on polyketides and pyrones. After completing his degree in 1885, Collie became science lecturer at Ladies’ College, Cheltenham, and remained there until 1887, when he went to University College, London, as assistant to William Ramsay. Collie was named professor of chemistry at the Pharmaceutical College, Bloomsbury Square, and fellow of the Royal Society in 1896. In 1902 he returned to University College, London, as the first professor of organic chemistry, a position he held until his retirement in 1928 as emeritus professor and honorary fellow of the college.

When Collie finished his studies on phosphonium salts, the lutidone derivative he had obtained earlier from heating β-aminocrotonic ester still piqued his interest. He managed to obtain this lutidone from dehydracetic acid and ammonia as well. This observation could not be reconciled with the then accepted structure for dehydracetic acid and Collie began to study this acid to understand its structure and chemistry. He proposed as dehydracetic acid 2-hydroxy, 6-acetonyl, γ-pyrone, or its δ-lactone tautomer, to explain its reactions. The acetone and carbon dioxide observed during the production of dehydracetic acid from tetraacetic acid were explained by the decomposition of unstable diacetic acid. This suggestion led to collie’s attempt to isolate triacetic acid or its lactone. He successfully obtained 4-hydroxy, 6-methyl, a-pyrone, the tautomeric 6-latone of triacetic acid, by hydrolysis of dehydracetic acid with sulfuric acid. With the finding of the postulated triacetic acid, Collie suggested the appropriate conditions for the condensation of tetra-, tri-, di-, and acetic acids into lactones.

Dehydracetic acid with hydrochloric acid yielded 2,6-dimethyl, γ-pyrone rather than a lactone. This finding, along with the observation that this pyrone ring could be opened to form diacetylacetone, suggested further studies. From diacetylacetone Collie succeeded in obtaining orcinol, symmetrical dimethylutidone, and various naphthalene and isoquinoline derivatives.

Collie culminated his work on dehydracetic acid, 2,6-dimethylpyrone, and diacetylacetone in his generalization of the multiple ketene group. What Collie called the ketene group (—CH₂CO—) and its enol tautomer(—CH=COH—) can, in one comprehensive scheme, relate pyrone, coumarin, benzopyrone, pyridine, isoquinoline, and naphthalene to the polyacetic acids. He also speculated on the formation of sugars and fats, with the multiple ketene group as the fundamental building block for these biological materials. Pentose sugars would be formed from pyrones and fats or acetogenins from acetic acid, depending on the hydrolysis of the multiple ketene group. The breadth of this early suggestion is just now being appreciated in biochemistry.

BIBLIOGRAPHY

I. Original Works. No collected volume of Collie’s works exists. Nearly all of his scientific papers were published in Journal of the Chemical Society from 1885 to 1920. Two key works are “Dehydracetic Acid,” in Journal of the Chemical Society, 71, pt. 2 (1900), 971–977; and “Derivatives of the Multiple Ketene Group,” ibid., 91 (1907), 1806–1813. Numerous articles appeared in various mountaineering journals, mainly in Alpine Journal. He also wrote two books, Climbing on the Himalaya and other Mountain Ranges (Edinburgh, 1902) and Climbs and Explorations in the Canadian Rockies (London, 1903).

II. Secondary Literature. An excellent biographical sketch, including a complete bibliography, appears in Obituary Notices of Fellows of the Royal Society of London, 4 no, 12 (Nov., 1943), 329–356. A notice on Collie appears in Dictionary of National Biography, supp. 6 (1941–1950), 167–168. A fine sketch highlighting Collie’s mountaineering appears in Alpine Journal, 54 , no, 266 (May, 1943), 59–65.

Gerald R. Van Hecke