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4
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JAMES FLACK NORRIS
January 20, 1871—August 4, 1940
BY JOHN D. ROBERTS
JAMES FLACK NORRIS was born in Baltimore, Maryland, Janu-
ary 20, 1871. He was the fifth of nine children, having two
brothers and two sisters older than himself. He therefore had
early opportunity to learn the art of getting along with people.
His father was a Methodist minister, a popular revivalist, and
a forceful orator in the pulpit. The future chemist used to ac-
company his father to camp meetings, where it was his custom
during the sermon to rest, perhaps to doze, on a bench behind
the pulpit, out of sight of the audience, and then later to stand
beside his father and lead the singing. He received his elemen-
tary education in the schools of Baltimore and Washington,
D.C. As a boy he collected stamps, but the pastime grew weari-
some and he exchanged the collection for a printing press. This
supplied means for the exercise of a more synthetic ingenuity,
and for two years he published a monthly literary newspaper for
which he wrote the articles and made the woodcuts himself.
Norris received the A.B. degree from Johns Hopkins in
1892, graduating Phi Beta Kappa, and remained at the univer-
sity for graduate work. He was Fellow in Chemistry, 1894-1895,
The bull; of this memoir was compiled from an article by Professor Tenney
. Davis, a colleague of James Flack Norris at the Massachusetts Institute of
Technology, which vitas published in Incl ustrial and Engineering Chemistry,
14:325-26 (1936). The present author has edited and extended this material to
bring it more into the usual format of the Memoirs.
413
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414
BIOGRAPHICAL MEMOIRS
and received the Ph.D. degree in 1895. At Hopkins he was a
member of the "Tramp Club," whose members were initiated
by being taken for a walk of twenty-five miles, and of the "House
of Commons," a debating society in which his classmate, New-
ton D. Baker, was especially active and articulate. Norris was
strongly attracted by Professor Ira Remsen and for three years'
running attended his lectures on organic chemistry and on the
history of chemistry. For his doctor's thesis, Remsen set him
to work on complex compounds of selenium and tellurium.
The lure of organic chemistry was strong, however, and the
investigation evolved into a study of the double salts of selenium
dichloride and tetrachioride with the aliphatic amines and
thence into a study of the perbromides and periodides of ali-
phatic amines, especially tertiary amines, in connection with
which the interesting observation was made that the amine
hydrobromides form perbromides by taking on a single atom of
bromine.
At the opening of the academic year in the fall of 1895 the
new Ph.D. joined the staff of the chemistry department of the
Massachusetts Institute of Technology. With him came Henry
Fay, also a Hopkins 1895 Ph.D. The two were close friends;
they went to the opera together and to parties at the homes of
President Walker and of various professors. Their appearance
and manners caused them to be envied by the younger members
of the staff as models of what the man-about-town ought to be.
The debonair Norris soon became known widely as "Sunny
Jim."
Norris remained at MIT until 1904, when he took on the
duties of the first professor of chemistry at Simmons College,
a newly organized college for women that was at the time just
opening in Boston. Here he outfitted the laboratories, organized
courses in chemistry, and had general supervision of all instruc-
tion in science. He stayed at Simmons until 1915 except for a
year of sabbatical leave. In 1915-1916 he was at Vanderbilt
University in Tennessee, then in the war, and back again to
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JAMES FLACK NORRIS
415
MIT, where he became professor of organic chemistry and
director of the Research Laboratory of Organic Chemistry after
its organization in 1926. He also gave courses at Harvard,
Radcliffe, Clark, and Bowdoin. From Bowdoin he received
the honorary Sc.D. in 1929. During his first period at MIT
he gave, among other courses, one in the history of chemistry,
having caught the contagion of that subject from Remsen. He
also taught advanced organic and inorganic chemistry, quali-
tative analysis, physical chemistry, food analysis—in fact, chem-
istry of all sorts except quantitative analysis.
Norris's sabbatical leave from Simmons was during the
academic year 1910-1911. Feeling the need for more physical
chemistry, he went to Karlsruhe, in Germany, where he worked
in the laboratory of Haber. Working there at that time were
a number of chemists who later became well known, including
Allemand, Robinson, Carter, and Askenasy. Norris wrote his
textbooks in North Bridgton on Long Lake, Maine, during the
summers of his period at Simmons. They were written with-
out the assistance of reference books, except tables of physical
constants, for the author believed that nothing ought to be
included in the general texts that a chemist does not remember
because he finds it useful.
At North Bridgton, Professor Norris worked in a cabin
among the trees, apart from the dwelling house, where he had
his study, a carpenter shop, a darkroom, and a laboratory. Here,
with no reagents except those he could buy at the country
grocery store and with no apparatus except a thermometer, a
graduate, and a horn-pan balance, he contrived a number of
experiments that are included in his inorganic laboratory
manual. He also experimented with photography and devised a
means of simultaneously developing and fixing the negative in
a single bath. Others had the same idea, and chemicals for this
purpose were put on the market shortly afterward by Lumiere
.
in ~ rance.
Professor Norris was an associate member of the Naval Con-
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416
suiting Board in 1916. In 1917-1918 he was in charge of chem-
ical research on agents of offense and war gas investigations of the
U.S. Bureau of Mines. He entered the Army as Lieutenant
Colonel in the Chemical Warfare Service. In 1918 he was in
charge of the U.S. Chemical Warfare Service in England and
in 1919 of the investigation of the manufacture of war gases in
German chemical plants. After the war he served ten years
as vice chairman and chairman (1924-1925) of the Division of
Chemistry and Chemical Technology of the National Research
Council and as a member of the Executive Board of the Council.
He was president of the American Chemical Society for two
years, 1925 and 1926, during which time he did much to im-
prove and clarify the finances of the Society. He was vice
president of the International Union of Pure and Applied
Chemistry from 1925 to 1928. He was made an honorary mem-
ber of the Rumanian Chemical Society, had lunch with Queen
Marie, and brought home a box of cigarettes, marked with the
royal monogram, from each of which he secured enjoyment and
satisfaction. He was also an honorary member of the Royal
Institute of Chemistry of Great Britain.
The American Institute of Chemists gave him its gold medal
in 1937 for "outstanding service as a teacher and as an investi-
gator." Norris was elected to membership in the National
Academy of Sciences in 1934. He was chairman of Section C
(chemistry) of the American Association for the Advancement
of Science in 1930.
A fitting tribute to his memory has been the James Flack
Norris Award of the Northeastern Section of the American
BIOGRAPHICAL MEMOIRS
Chemical Society. The award originally recognized outstanding
teaching in chemistry, but more recently has been for research
in physical organic chemistry.
Although Norris was serious when occasion demanded it,
profoundly interested in his work, and dignified to a degree'
he was "Jimmie" to a host of friends who found him a gay com-
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JAMES FLACK NORRIS 417
panion when there was no work at hand and the cheerful
member of many an informal group. He was married in Wash-
ington, D.C., February 4, 1902, to Anne Bent, daughter of
Lowell Augustus Chamberlin, Captain, U.S. Army; they had
no children. James Flack Norris died in Cambridge, Massa-
chusetts, on August 4, 1940.
The scientific work of James Flack Norris, insofar as may be
judged by his seventy-odd scientific papers, was broadly inter-
esting and important, but hardly had the impact of the work of
some of his contemporaries in America, such as Gomberg,
Stieglitz, and Nef, because he sometimes reached the wrong con-
clusions. Thus, at almost the beginning of his MIT career,
Norris became engaged in, and lost, rather a vitriolic argument
with Gomberg about the nature of triphenylmethyl. Norris
held that Gomberg's analytical data were incorrect and that the
"unsaturated hydrocarbon" formed from triphenylchlorometh-
ane and zinc in benzene was formed with loss of hydrogen
chloride. He believed the correct structure to be (C6H,) C_
C6H4, but did not specify just how the "phenylene" part of the
molecule was arranged, although he clearly recognized that it
was likely to react easily with oxygen.
After continuation of some work on selenium and tellurium,
begun with Remsen, Norris became rather generally concerned
with some of the preparations and reactions of relatively simple
compounds such as those that made up the backbone of the syn-
thetic aliphatic chemistry of the time. Thus, he and his students
investigated the conversions of alcohols to halides and the re-
actions of these halides with hydrocarbons by Friedel-Crafts
catalysts to build up more complex substances.
As a result of these studies, in which it must have become
clear to him that there were large differences in reactivity
associated with rather similar substances in the same preparative
reaction, he published in 1925 the first of what was to be a
twenty-paper series on "the reactivity of atoms and groups in
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418
organic compounds." Much, but not all, of this work was con-
cerned with the rates of the reaction of alcohols with acyl
halides. These studies began before the mechanisms of any of
the reactions involved were known and, necessarily, wound up
providing only empirical correlations. The correlations were
useful nonetheless for planning synthetic work and for pointing
to striking differences in behavior that would ultimately require
explanation. An example of the latter was the discovery of a
2,800-fold greater reactivity of 4,4'-dimethyldiphenylchloro-
methane relative to 4,4'-dichlorodiphenylchloromethane toward
ethyl alcohol in a reaction that is rather well, but still not per-
fectly, understood forty-five years later. This program involved
two of the best-known Ph.D. students Norris had—A. A. Ash-
down (who later became the storied master of MIT's graduate
student house) and, three years subsequently, A. A. Morton
(discoverer of the elfin polymerization catalyst and many inter-
esting metalation reactions). The research on reactivity was
extended gradually to include thermal decompositions of ma-
lonic acids, and certain parallels were noted between the effect
of R as an or substituent in influencing the carboxylation of
malonic acid and the effect of R in ROH in changing reactivity
toward p-nitrobenzoyl chloride.
Norris was rather less successful in his work on reactivity
than was his younger counterpart at Harvard, James B. Conant,
who displayed an almost unerring instinct for choosing reactions
for study of greater simplicity and involving wider ranges of
reactivity, along with an excellent feel for the basic physical
chemistry involved. Nonetheless, Norris had the prescience to be
at the forefront of the still-developing area of making compari--
sons of organic reactivity under controlled conditions, and some
of the reactions he was first to study are among the most im-
portant in preparative chemistry.
BIOGRAPHICAL MEMOIRS
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JAMES FLACK NORRIS
BIBLIOGRAPHY
KEY TO ABBREVIATIONS
Aim. Chem. i. =.American Chemical Journal
Ind. Eng. Chem. Industrial and Engineering Chemistry
I. Am. Chem. Soc. = {ournal of the American Chemical Society
I. Ind. Eng. Chem.—journal of Industrial and Engineering Chemistry
Org. Syn. = Organic Syntheses
1896
419
With I. Remsen. The action of the halogens on the methylamines.
Am. Chem. I., 18: 90.
With H. Fay. Iodometric determination of selenious and selenic
acids. Am. Chem. l., 18:703.
1898
With E. H. Laws, F. M. Smalley, and A. E. Kimberley. The action
of the halogens on the aliphatic amines and the preparation
of their perhalides.
With H. Fay.
20:278.
Some double salts containing selenium.
Am. Chem. l., 20:51.
Iodometric estimation- of tellurium.
1899
With A. I. Franklin.
Am. Chem. J.,
Am. Chem. l., 20:490.
The composition of nitrogen iodide and the
action of iodine on the fatty amines.
1900
— - — c7 -
Am. Chem. J., 21:499.
With H. Fay and 1). W. Edgerly.
lurium. Am. Chem. l., 23:105.
With H. Fay. The reduction of selenium dioxide by sodium thio-
sulphate. Am. Chem. l., 23:119.
With R. Mommers. On the isomorphism of selenium and tellu-
rium. Am. Chem. l., 23:486.
1901
The preparation of pure tel-
With W. W. Sanders. On triphenylchlormethane. Am. Chem. J.,
25:54.
On the nonexistence of trivalent carbon. Am. Chem. l., 25:117.
OCR for page 440
420
BIOGRAPHICAL MEMOIRS
With E. H. Green. Some new derivatives of secondary butyl al-
cohol. Am. Chem. J., 26:293.
With B. R. Rickards. Reduction of secondary butyl alcohol, etc.
Am. Chem. i., 26:303, 305, 307.
With H. G. Johnson.
26:308.
With W. A. Kingman.
Am. Chem. i., 26:318.
With E. H. Green. Condensation of carbon tetrachloride with
halogen derivatives of benzene by means of the Friedel and
Crafts reaction. Am. Chem. l., 26:492.
With G. MacLeod. On the preparation of triphenylmethane. Am.
Secondary butyl bromide.
Am. Chem. I.,
Isomorphism of selenates and tellurates.
Chem. J., 26:499.
1903
With B. G. MacIntire and W. M. Corse. The decomposition of
diazonium salts with phenols. Am. Chem. l., 29: 120.
With L. R. Culver. The action of zinc on triphenylchlormethane.
Am. Chem. i., 29:129.
With D. R. Franklin. The action of zinc on benzoyl chloride. Am.
Chem. i., 29:141.
The action of zinc on triphenylchlormethane.
29:609.
With W. C. Twieg. The condensation of carbon tetrachloride with
chlorbenzene by means of the Friedel and Crafts reaction. Am.
Chem. J., 30:392.
II. Am. Chem. J.,
1906
On the elementary nature and atomic weight of tellurium. l. Am.
Chem. Soc., 28:1675-84.
1907
On the base-forming property of carbon. Am. Chem. l., 38:627.
1910
With R. Thomas and B. M. Brown. Action of metals on ketone
chlorides of the aromatic series and properties of compounds of
the type R2CClCClR2. Berichte der Deutschen Chemischen
Gesellschaft, 43: 2940-59.
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JAMES FLACK NORRIS
1915
Experimental Organic Chemistry.
Co. Inc.
' 1916
421
New York, McGraw-Hill Book
Organic molecular compounds. l. Am. Chem. Soc., 38:702-11.
With M. Watt and R. Thomas. Reaction between alcohols and
aqueous solutions of hydrochloric and hydrobromic acids. l.
Am.Chem.Soc., 38:1071-79.
1919
Manufacture of war gases in Germany. l. Ind. Eng. Chem., 11:817-
29.
1920
With D. M. Tibbets. Organic molecular compounds. II. l. Am.
Chem. Soc., 42:2085-92.
With R. S. Mulliken. Reaction between alcohols and aqueous
solutions of hydrochloric and hydrobromic acids. II. l. Am.
Chem. Soc., 42:2093-98.
With H. B. Couch. Condensation of benzoyl chloride with ethylene
in the presence of aluminum chloride. I. Am. Chem. Soc.,
42:2329-32.
1921
A Textbook of Inorganic Chemistry for College.
Graw-Hill Book Co., Inc.
1922
New York, Mc-
The Principles of Organic Chemistry. 2d ed. New York, McGraw-
Hill Book Co., Inc.
1923
With K. L. Mark. Laboratory Exercises in Inorganic Chemistry.
New York, McGraw-Hill Book Co., Inc.
1924
New catalytic effects of zinc chloride and aluminum chloride. Ind.
Eng. Chem., 16:184.
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422
BIOGRAPHICAL MEMOIRS
With H. B. Taylor. Preparation of alkyl chlorides. l. Am. Chem.
Soc., 46:753-57.
With R. C. Young. Preparation of triphenylmethane and the
action of heat on the ethers and esters derived from triphenyl-
carbinol. l. Am. Chem. Soc., 46:2580-83.
Experimental Organic Chemistry. 2d ed. New York, McGraw-
Hill Book Co., Inc.
1925
With A. A. Ashdown. The reactivity of atoms and groups in or-
ganic compounds. I. The relative reactivities of the hydroxyl-
hydrogen atoms in certain alcohols. I. Am. Chem. Soc., 47:837-
46.
With E. O. Cummings. Electrolytic preparation of p-phenylene-
diamine, aminosalicylic acid, succinic acid and hydrocinnamic
acid. Ind. Eng. Chem., 17:305-7.
Roger Frederic Brunel (biography).
Butyl chloride. Org. Syn., 5:27-29.
1927
Science, 61 :407-8.
With i. M. ioubert. Polymerization of the amylenes. l. Am.
Chem. Soc., 49: 873-86.
With R. Renter. Rearrangement of isopropylethylene to trimethyl-
ene and the pyrogenic decomposition of 2-pentene and tri-
methylene. i. Am. Chem. Soc., 49:2624-40.
With F. Cortese. The reactivity of atoms and groups in organic
compounds. II. Second contribution on the relative reactivities
of the hydroxyl-hydrogen atoms in certain alcohols. J. Am.
Chem. Soc., 49: 2640-50.
The chemical reactivity of atoms and groups in organic compounds.
Zeitschrift fur Physikalische Chemie, 130:662-72.
2-Pentene. Org. Syn., 7:76-77.
1928
With A. A. Morton. The reactivity of atoms and groups in organic
compounds. III. First contribution on the carbon-chlorine
bond: The rate of the reaction between diphenylchloromethane
and ethyl alcohol. J. Am. Chem. Soc., 50: 1795-1803.
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JAMES FLACK NORRIS
With C. Banta
423
t. The reactivity of atoms and groups in organic com-
pounds. IV. The rates of reactions of certain derivatives of
diphenylchloromethane with ethyl alcohol and with isopropyl
alcohol. l. Am. Chem. Soc., 50:1804-8.
With i. T. Blake. The reactivity of atoms and groups in organic
compounds. V. The rates of the reactions of certain derivatives
of diphenylchloromethane with ethyl alcohol.
Soc., 50:1808-12.
With D. V. Gregory.
I. Am. Chem.
The reactivity of atoms and groups in organic
compounds. VI. The rates of the reactions of benzoyl chloride
and certain of its derivatives with isopropyl alcohol. i. Am.
Chem. Soc., 50:1813-16.
With S. W. Prentiss. The reactivity of atoms and groups in organic
compounds. VII. The influence of certain solvents on reaction
velocity-adj uvance.
I. Am. Chem. Soc., 50:3042~8.
With A. W. Olmsted. tert-Butyl chloride. Org. Syn., 8:50-51.
American contemporaries—Arthur D. Little. Ind. Eng. Chem.,
20: 1395-96.
1929
With H. S. Davis. Production of alcohols from the butenes and
pentenes through interaction with sulfuric acid. Journal of the
Society of Chemical Industry, 48:70.
With W. S. Johnson, H. D. Hirsch, and C. R. McCullough. The
reactivity of atoms and groups in organic compounds. VIII.
The relative reactivities of the hydroxyl groups in certain al-
cohols. Recueil des Travaux Chimiques des Pays-gas, 48:885-
89.
1930
With R. C. Young. The reactivity of atoms and groups in organic
compounds. X. The measurement of the relative lability of
bonds by means of rates of reactions and of temperatures of de-
composition. I. The hydrogen-oxygen bond in certain alcohols.
I. Am. Chem. Soc., 52:753-61.
With R. C. Young. The reactivity of atoms and groups in organic
compounds. XI. The influence of the structure of the substi-
tuent on the temperature of decomposition of certain derivatives
of malonic acid. l. Am. Chem. Soc., 52:4066-69.
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424
BIOGRAPHICAL MEMOIRS
1931
With G. Thomson. Significant temperatures in the pyrolysis of
certain pentanes and pentenes. J. Am. Chem. Soc., 53:3108-15.
1932
With G. W. Rigby. The reactivity of atoms and groups in organic
compounds. XII. Preparation and properties of mixed aliphatic
ethers with special reference to those containing the tert-butyl
radical. T. Am. Chem. Soc., 54:2088-2100.
Significance of pyrolysis temperatures. Journal of Chemical Edu-
cation, 9: 1890-96.
1933
With H. F. Tucker. The reactivity of atoms and groups in organic
compounds. XIV. Influence of substituents on the thermal
stability of certain derivatives of malonic acid. J. Am. Chem.
Soc., 55:4697-704.
With A. Cresswell. Rates of the thermal decomposition of certain
triphenylmethyl alkyl ethers. J. Am. Chem. Soc., 55:4946-51.
1935
With W. H. Strain.
The reactivity of atoms and groups in organic
compounds. XV. The relative reactivities of the hydrogen of the
hydroxyl group in benzoic acid and certain of its derivatives.
I. Am. Chem. Soc., 57:187-92.
With E. V. Fasce and C. J. Stand. The reactivity of atoms and
groups in organic compounds. XVI. The relative effects of sub-
stituents on the rates at which certain acyl and alkyl chlorides
react with ethyl alcohol. l. Am. Chem. Soc., 57:1415-20.
With H. H. Young, Jr. The reactivity of atoms and groups in or-
ganic compounds. XVII. The effect of the change in reactant
and of the temperature on the relative reactivities of certain
substitution products of benzoyl chloride. l. Am. Chem. Soc.,
57: 1420-24.
With E. C. Haines. The reactivity of atoms and groups in organic
compounds. XlIIII. The effect of the solvent on the rate of the
reaction between benzoyl chloride and ethyl alcohol. J. Am.
Chem. Soc., 57:1425-27.
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JAMES FLACK NORRIS
425
1938
With I. N. Ingraham. Condensation of aliphatic alcohols with
aromatic hydrocarbons. I. The preparation of mesitylene and
sym-triethylbenzene. I. Am. Chem. Soc., 60:1421-23.
1939
With D. Rubinstein. Formation of intermediate compounds in
hydrocarbon syntheses by the Friedel and Crafts reaction and the
preparation of certain symmetrical trialkylbenzenes. J. Am.
Chem. Soc., 61:1163-70.
With B. M. Sturgis. Condensation of alcohols, ethers and esters
with aromatic hydrocarbons in the presence of aluminum chlo-
ride. i. Am. Chem. Soc., 61:1413-17.
With V. W. Ware. The reactivity of atoms and groups in organic
compounds. XIX. The relative reactivities of the chlorine
atoms in certain derivatives of benzoyl chloride. i. Am. Chem.
Soc., 61: 1418-20.
With H. S. Turner. Rearrangement of certain derivatives of
toluene by the action of aluminum chloride. l. Am. Chem.
Soc., 61:2128-31.
With G. T. Vaala. Rearrangement of the xylenes by aluminum
chloride. J. Am. Chem. Soc., 61 :2131-34.
With K. L. Mark. Laboratory Exercises in Inorganic Chemistry.
2d ed. New York, McGraw-Hill Book Co., Inc.
1940
With P. Arthur, in Condensation of esters with aromatic hydro-
carbons by means of aluminum chloride. I. Am. Chem. Soc.,
62: 874-77.
With A. E. Bearse. The reactivity of atoms and groups in organic
compounds. XX. The effect of substituents on the relative re-
activities of the hydroxyl group in derivatives of benzoic acid.
i. Am. Chem. Soc., 62:953-56.
With J. N. Ingraham. Certain trialkylated benzenes and their com-
pounds with aluminum chloride and with aluminum bromide.
J. Am. Chem. Soc., 62:1298-1301.
With i. E. Wood III. Intermediate complexes in the Friedel and
Crafts reaction. l. Am. Chem. Soc., 62: 1428-32.
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426
BIOGRAPHICAL MEMOIRS
With A. l. Klemka. Preparation of nitrites and amides. Reactions
of esters with acids and with aluminum chloride. The use of
the salt NaC1 · A1C13 in the Friedel and Crafts reaction. l. Am.
Chem. Soc., 62:1432-35.
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Representative terms from entire chapter:
flack norris
