Louisiana State University LSU Digital Commons LSU Historical Dissertations and eses Graduate School 1963 Reactions of Lithium Nitride With Some Unsaturated Organic Compounds. Perry S. Mason Jr Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: hps://digitalcommons.lsu.edu/gradschool_disstheses is Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and eses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. Recommended Citation Mason, Perry S. Jr, "Reactions of Lithium Nitride With Some Unsaturated Organic Compounds." (1963). LSU Historical Dissertations and eses. 898. hps://digitalcommons.lsu.edu/gradschool_disstheses/898
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Louisiana State UniversityLSU Digital Commons
LSU Historical Dissertations and Theses Graduate School
1963
Reactions of Lithium Nitride With SomeUnsaturated Organic Compounds.Perry S. Mason JrLouisiana State University and Agricultural & Mechanical College
Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses
This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion inLSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please [email protected].
Recommended CitationMason, Perry S. Jr, "Reactions of Lithium Nitride With Some Unsaturated Organic Compounds." (1963). LSU Historical Dissertationsand Theses. 898.https://digitalcommons.lsu.edu/gradschool_disstheses/898
*Lithium nitride from Foote Mineral Company was used in this and in all subsequent reactions.
Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.
33
Nitrogen was passed into the flask to displace the air, the third
neck was stoppered, and the mixture was heated to reflux while
stirring. Again the blue colored solution was noted which in turn
gave way to a brown solution upon continued heating. This time it
was also noticed that the formation of ‘he brown solid was
accompanied by liberation of considerable anmonia.
At the end of three hours, 35 ml. of diglyme were removed by
distillation and the residue was poured into water. Acidification
of the solution caused a brown oil to separate which was extracted
into ether. The ethereal layer was separated, dried, and the ether
evaporated, leaving 11.0 g. of dark oil. All of this residue was
then passed through a chromatographic column filled with activated
alumina using petroleum ether as the eluent. Evaporation of the
petroleum ether eluent gave 8.8 g. of benzophenone, m.p. 48.5-49.4°,
mixed melting point 48.7-49.5°. No other compound was eluted even
with more polar solvents.
Third Run. A 500-ml. three-necked flask was fitted with a
Friedrich condenser and a mercury-sealed stirrer. A rubber tube
was passed from the top of the condenser to an inverted graduated
cylinder filled with water. To this flask was added 18.2 g.
(0.10 mole) of benzophenone, 5.0 g. (0.14 mole) of lithium nitride,
and 100 ml. of tetrahydrofuran. After the air in the flask was
displaced with nitrogen, the third neck was stoppered, the stirrer
was started, ;..td the contents of the flask were heated to reflux.
A deep blue color began to be evident after several minutes; at
about the same time, a gas began to collect in the graduated
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cylinder* The reaction was allowed to proceed until the liberation
of gas had definitely ceased (about 36 hours). The volume of gas
was found to be 380 ml. (0.016 mole using the ideal gas equation)
at 22° and 746 mm. pressure after correcting for expansion.
Ammonium chloride (15 g.) was added to the flask and reflux
was resumed for 12 more hours. The reaction mixture was then
filtered, and the filtrate was heated on the steam cone to evapo
rate the solvent. All efforts to isolate a pure compound from
the residue were unsuccessful.
Reaction of Lithium Nitride with Benzil
Benzil was purified by recrystallization from ethanol, m.p.
95.0-96.0°.
First Run. A 200-ml. round-bottomed flask was equipped with
a Friedrich condenser and a mercury-sealed stirrer. To this flask
was transferred 5.0 g. (0.024 mole) of benzil, 2.0 g. (0.058 mole)
of lithium nitride, and 60 ml. of diglyme. The air in the flask
was displaced with nitrogen, the stirrer started, and the contents
of the flask brought to reflux.
After about ten minutes, a deep red color began to develop.
This color slowly changed and a yellow solid appeared, the change
appearing complete after one hour.
A separatory funnel was put in place of the stopper on the
third neck and 3.0 g. (0.029 mole) of acetic anhydride was slowly
dripped into the flask, stirring being continued. The yellow
precipitate disappeared and a red solution remained at the end of
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35
this addition. The reaction mixture was filtered while still hot,
and the deep red filtrate treated with decolorizing charcoal. No
change in color resulted from this treatment and all efforts to
isolate any compound from the solution were unsuccessful.
Second Run. Into a 500-ml. three-necked flask, equipped with
a separatory funnel, a Friedrich condenser, and a mercury-sealed
stirrer, were placed 5.0 g. (0.14 mole) of lithium nitride, and
50 ml. of diglyme. A solution of 10 g. (0.048 mole) of benzil
in 100 ml. of diglyme was placed in the separatory funnel. After
displacing the air in the flask with nitrogen, this solution was
dripped into the flask while the reaction mixture was stirred and
maintained at the temperature of reflux.
The reaction did not appear to be taking the same course
as before; the solution turned red as before, but led to a dark
brown viscous solution instead of the light yellow solid. The
formation of the dark solution took place rather suddenly and
was accompanied by the liberation of anmonia.
Heating was continued for a total of 5 1/2 hours, then the
Friedrich condenser was replaced with a Nest condenser and 110 ml.
of diglyme was removed by distillation. The reaction mixture,
when cool, was poured into about 200 ml. of ice water. A brown
precipitate formed which was separated by filtration and washed
with water. It was found to give a lithium flame test, and was
therefore treated with dilute hydrochloric acid. A dark brown oil
resulted which could not be crystallized nor distilled under vacuum.
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36
Third Run. Lithium nitride was reacted with benzil as in the
previous run, except that the benzil solution was added a little
more rapidly. The course of the reaction this time corresponded
to the first run in that the final product was a yellow solid.
The addition of the benzil solution was complete after two
hours. Keating was continued for an additional hour, then 70 ml.
of diglyme were removed by distillation. The residue was poured
with stirring into about 200 ml. of ice water. Acidification of
the mixture caused a brown oil to settle to the bottom. This was
taken up into ether, the ether layer was extracted with potassium
carbonate solution, and the carbonate layer neutralized with
hydrochloric acid to give 10 g. (still slightly damp) of brown
solid. Treatment with decolorizing charcoal and recrystallization
from ethanol yielded 5.0 g. (45%) of clear crystals, m.p. 152.0-
153.5°. These were identified as benzilic acid (lit.,^ m.p.
150°). The g^-bromophenacyl ester melted at 152.0-153.0° (lit.,^®
m.p. 152°). The infrared spectrum of the crystals indicated that
the compound was benzilic acid and was identical to the spectrum69given for it in the Sadtler Indices.
Fourth Run. The reaction of lithium nitride with benzil was
repeated as in the previous run in an effort to increase the yield
of benzilic acid. The benzil solution was added over a period of
one hour, but the mixture was heated for four hours afterward. The
final product this time was again the dark brown solution. The
yield of benzilic acid proved to be lower this time; only 2.9 g.
of the acid was obtained.
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37
Reactioa of Lithium Nitride with Acetone
First Run. To a 500-ml. three-necked flask equipped with a
stirrer and condenser was added 4.0 g» (0.11 mole) of lithium
nitride and 200 ml. of acetone. The air was displaced with nitrogens
then the stirred mixture was heated to reflux. A vigorous reaction
soon started which liberated ammonia, so that it was necessary to
remove the mantle and cool the flask occasionally. A gray colored
salt formed in the flask during the course of the reaction, making
the mixture viscous and hard to stir. When the reaction had ceased,
the flask was allowed to cool, then its contents were scraped into
about 150 ml. of water. The organic layer was removed and the
water layer was extracted with ether. The combined extracts were
dried with sodium sulfate and fractionally distilled to yield
21.4 g. of mesityl oxide, b.p. 127-129°, n^° - 1.4432 (lit.,70
b.p. 130-131°, n^° : 1.443S7). The melting point of the 2,4-
dinitrophenylhydrazone was 201.0-202.2° (lit.,7^ m.p. 200°). The
infrared spectrum confirmed the mesityl oxide structure.
There was also obtained 2.1 g. of isophorone, b.p. 89° at
11 mm., n^° = 1.4751 (lit.,7^ n^p*"* a 1.4789). The melting point
of the semicarbazone was 197.5-199.0° (lit.,7^ m.p. 199.5°).
Second Run. Acetone was again reacted with lithium nitride,
but this time the acetone was added slowly to the base to try to
increase the yield of isophorone relative to that of mesityl oxide.
To a 500-ml. three-necked flask equipped as in the previous
run, except for a dropping funnel, was added 3„5 g. (0.10 mole)
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38
of lithium nitride and 200 ml. of tetrahydrofuran. The stirrer
was started and the mixture was brought to reflux. Through the
dropping funnel was slowly added 27 g. (0.46 mole) of acetone.
Upon completion of the addition (requiring about one hour) the
contents were allowed to reflux for an additional hour, then 10 g.
of water was added through the funnel. After stirring for a few
more minutes, the reaction mixture was filtered at the aspirator.
The salt was washed with a few milliliters of tetrahydrofuran
and the filtrate was fractionally distilled to give 7.0 g. of
isophorone, b.p. 82-84° at 9 mm., n ^ = 1.4749 (lit.,7^ =
1.4789). The melting point of the 2,4-dinitrophenylhydrazone was
129.5-131.0° (lit.,73 m.p. 130°).
In addition there was obtained 2.9 g. of mesityl oxide,
identified only by boiling point and odor (b.p. 127-130°).
Several grams of material would not distil over; it
solidified upon cooling. After recrystallization from ether,
vacuum sublimation, and recrystallization from petroleum ether,
4.1 g. of clear platelets were obtained, melting at 127.5-128.5°.
These decolorized bromine solution and gave a precipitate with
2,4-dinitrophenylhydrazone. The infrared spectrum was very
similar to that for isophorone. Elemental analysis indicated
the absence of nitrogen and gave the following results for carbon
and hydrogen: C, 75.47%; H, 9.977.. This corresponds to an
empirical formula of CjH^O. Cryoscopic determination of the
molecular weight gave a value of 194, which indicates the formula
to be C 1 4 H2 2 O 2 •
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39
Third Run. In this run, which employed the same set-up as in
the previous run, the acetone was dripped into the flask very slowly
to try to increase the yield of the unidentified crystals. Tetra
hydrofuran (200 ml.) and 5.0 g. (0.14 mole) of lithium nitride
were heated to reflux and 31.0 g. (0.53 mole) of acetone was
dripped into the flask over a period of 1 1/2 hours. The reaction
mixture was stirred at the temperature of reflux for an additional
1/2 hour, then 20 ml. of water was dripped into the flask.
Magnesium sulfate was added to remove the excess water, then the
salts were removed by filtration. The filtrate was fractionally
distilled to give a trace of mesityl oxide and 6.9 g. of isophorone.
The residue was recrystallized from ether, vacuum sublimed, and
recrystallized from petroleum ether to give 9.2 g. of clear
crystals, m.p. 128.0-128.5°.
Reaction of Lithium Nitride with Benzonitrile
First Run. A small amount of benzonitrile was refluxed with
lithium nitride in a test tube using diglyme as a solvent to see
if any reaction would occur. The mixture was refluxed for an hour.
No change was observed in the lithium nitride but the solution*
turned green. When cool, the contents of the test tube was care
fully poured into water. A small amount of green crystals formed;
these were removed by filtration and found to melt at 230-231°.
This reaction was repeated on a larger scale; 5.0 g. of
benzonitrile was refluxed with 0.5 g. of lithium nitride in 2 ml.
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40
of diglyme for one hour. Pouring the reaction mixture into water
again gave a green solid. However, during investigation of various
solvents for recrystallization, it was noticed that the crystals
themselves were clear in color and were much more soluble in
solvents of low polarity than those of high, while the green color
was due to a green oil which was soluble in most solvents but
favored those of higher polarity.
The best solvent was found to be tetrahydrofuran, and re
crystallization from this gave 0.8 g. of clear crystals, m.p,
233.5-234.0°. These were soluble in ether, but insoluble in water,
dilute hydrochloric acid and sodium hydroxide solution. A sodium
fusion was carried out and the test for nitrogen was positive.
Some of the crystals were refluxed in alcoholic sodium hydroxide
solution but no reaction was observed.
The crystals were soluble in concentrated sulfuric acid.
Addition of water to the resulting solution precipitated crystals
melting over a wide range below 230°. Since this seemed to indicate
that the sulfuric acid had partially decomposed the crystals, all
these that were left were also dissolved in sulfuric acid, and a
few drops of water was added. The addition caused precipitation
from the solution in the immediate region of the drop, but it
redissolved upon agitation of the acid solution. The solution was
allowed to stand on the steam cone overnight. When a few drops
of water was now added, no precipitation occurred. It was noticed,
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41
however, that a few crystals had formed around the rim of the
beaker in which the solution had been heated. These were found
to melt at 120-121°.
Second Run. To a 200-ml. three-necked flask equipped with
a condenser and a stirrer was added 20 g. of benzonitrile (which
had been distilled, b.p. 190-191°), 2.4 g. (0.07 mole) of lithium
nitride, and 75 ml. of diglyme. The air was displaced with
nitrogen and the contents of the flask were refluxed for 7 hours.
Crystals formed in the flask when it was allowed to stand over
night. These were scraped out and recrystallized from tetrahydro
furan to give 5.0 g. of clear crystals, m.p. 233.5-234.5°.
A sulfuric acid solution of these crystals, containing 10 g.
of concentrated sulfuric acid and 4.5 g. of the crystals, was*
placed in a sublimation apparatus. After adding 2 ml. of water,
the solution was maintained at 110° for 14 hours to give 1.5 g.
of a clear crystalline sublimate. This melted at 118-120°, 120-
122° after recrystallization from water, and was soluble in
sodium bicarbonate solution. From these data the sublimate was
tentatively identified as benzoic acid. Part of the sulfuric
acid solution remaining was neutralized with sodium hydroxide
and heated to boiling in a test tube. The vapor had the odor of
ammonia and turned red litmus paper to blue.
It now seemed that the original product from benzonitrile
was 2,4,6-triphenyl-l,3,5-triazine. A comparison of the infrared
spectrum with that for an authentic sample of the triazine
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42
(supplied by Mr. Robert Dunmire) indicated that this was indeed the
case. A mixed melting point of 233-234° was observed with this
sample.
Third Run. The reaction was run in the same manner as in
the previous run to try to increase the yield. There was obtained
12.0 g. (60%) of product melting at 233.5-234.5°.
Fourth Run. The trimerization of benzonitrile was repeated
under slightly different conditions: a 500-ml. three-necked flask
equipped with a Friedrich condenser, stirrer, and thermometer was
used. To it was added 2.0 g. of lithium nitride, 40.0 g. of
benzonitrile, and 100 ml. of diglyme. After sweeping cut the
system with nitrogen, the mixture was stirred for 15 hours at 150°.
At the end of this heating period, the solution was brown instead
of the green color previously observed.
Upon cooling, the solution yielded crystals of 2,4,6-triphenyl-
1,3,5-triazine, which were removed by filtration. Water was added
to the filtrate to give a second crop. The lithium nitride was
removed from the crystals by washing with methanol (the triazine
had been found to be virtually insoluble in this solvent) then
with water. A total yield of 36 g. (90%) of crude product was
obtained. This was recrystallized from tetrahydrofuran to give
29 g. (72.6%) of 2,4,6-triphenyl-l,3,5-triazine, m.p. 232.6-234.5°.
Reaction of Benzonitrile with Metallic Lithium
To a 100-ml. three-necked flask equipped with a condenser
and a stirrer was added 10 g. of benzonitrile, 25 ml. of diglyme,
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43
and a small piece of lithium (0.05 g.) which had been flattened
to expose more surface area. These were heated to the temperature
of reflux and stirred for 13 hours. The reaction mixture at this
time was blue-green in color; when it cooled no crystals formed.
The lithium was manually removed from the solution. The addition
of water gave a green oil which would not crystallize, but upon
addition of methanol yielded 0.75 g. (7.5%) of 2,4,6-triphenyl-
1,3,5-triazine, m.p. 232-234°.
Reaction of Lithium Nitride with Acetonitrile
Acetonitrile was purified by shaking with solid potassium
carbonate and distilling, b.p. 81-82°.
Low-boiling Solvent. A 200-ml. three-necked flask was
equipped with a condenser and a stirrer. To it was added 20,5 g.
(0.5 mole) of acetonitrile, 3.0 g. (0.086 mole) of lithium nitride,
and 80 ml. of petroleum ether. The air was displaced with
nitrogen, the stirrer was started, and the contents of the flask
were refluxed 3 1/2 hours. A slow evolution of ammonia and the
formation of a white solid occurred during the reaction period.
The solid material was removed by filtration and hydrolyzed with
20 ml. of saturated ammonium chloride. The organic layer which
resulted was extracted into ether; evaporation of the ether gave
a solid which was recrystallized from ether-petroleum ether mixture
tc give 9.0 g. (44%) of 3-iminobutyronitrile, m.p. 52-54° (lit.,^
m.p. 52°). Treatment with phenylhydrazine in aqueous alcoholic solution gave the phenylhydrazone of 3-ketobutyronitrile, m.p. 104-105° (lit.,74 m.p. 101°).
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44
High-boiling Solvent. To a 200-ml. three-necked flask,
equipped with a condenser and a stirrer, was added 20.5 g. (0.5
mole) of acetonitrile, 2.0 g. (0.58 mole) of lilhium nitride, and
25 ml. of diglyme. The air was displaced with nitrogen, the
stirrer was started, and the contents of the flask were refluxed
for 4 hours.
After cooling, the solids were filtered from the diglyme.
Addition of a small amount of the salt to water gave no organic
layer, so it was hydrolyzed by stirring with anmonium chloride
in refluxing tetrahydrofuran solution for 20 hours. The solution
was then filtered and the filtrate was heated on the steam bath
to evaporate the tetrahydrofuran. Crystals were obtained which
were purified by vacuum sublimation to give 8.1 g. (40%) of clear
crystals, m.p. 179-181° (lit.,^ m.p. for 4-amino-2,6-dimethyl-
pyrimidine, 181°). A mixed melting point of 180-181° was observed
with an authentic sample of 4-amino-2,6-dimethylpyrimidine, pre-62pared as outlined by Reynolds ejt a l .
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C O N C LU SIO N
It must be concluded from the work which was done that
lithium nitride is of little practical value as a laboratory
reducing agent. In many cases no reduction was observed at all.
When reduction did occur the reaction generally was unsatisfactory,
giving low yields and side-products. Furthermore, when a reaction
took place once, it often could not be made to occur again or it
might lead to different products. The fact that any reduction
was observed at all at least indicates that the theoretical
predictions were not completely out of line.
The results of this investigation have added to the knowl
edge of the chemistry of lithium nitride. All indications are
that lithium nitride, in addition to being a relatively ineffectual
reducing agent, is also a poor nucleophile. This is especially
indicated in the reaction with cyclohexyl-]5-toluenesulfonate.
This observation can be explained on the basis that the nitride
ion cannot effectively initiate a back-side attack while in the
crystalline lattice.
45
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46
. In contrast to the conditions required in most of the reactions
of lithium nitride, its reactions with active hydrogen compounds are
surprisingly facile* This can also be explained on the basis of
steric requirements; there should be relatively little hindrance
involved for a hydrogen to move close enough to the surface of a
lithium nitride crystal to be abstracted as a proton.
Most of the reactions of lithium nitride with organic com
pounds indicate that the nitride reacts as a strong base. This
property evidently overshadows the tendency of the nitride to act
as a reducing agent.
The trimerization of benzonitrile by lithium nitride indicates
that lithium nitride can be very effectual in heterogeneous
catalysis.
A large part of the difficulty encountered in the reactions
of lithium nitride is no doubt due to the high lattice energy and
the accompanying insolubility. Rather extreme conditions are
therefore required to get a reaction to take place at all, and
under these conditions tarring, etc. is prevalent and the reactions
are often unsatisfactory. If some way could be found to disrupt
the lattice of lithium nitride and allow the nitride ion to react
under more moderate conditions, lithium nitride might prove to be
a very useful reagent in organic chemistry.
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59. A. Cook and K. Jones, J. Chem. Soc., 1941, 278.
60. E. Earl Royals, "Advanced Organic Chemistry," Prentice-Hall,New York, N. Y., 1954, p. 205.
61. G. A. Reynolds, W. Humphlett, and F. W. Swamer, J. Org. Chem.,16, 165 (1951).
62. "The Sadtler Indices," Sadtler Research Laboratories,Philadelphia, Pa., 1951, Spectrum No. 350.
63. A. I. Vogel, 0 £. cit., p. 631.
64. V. C. Sekera and C. S. Marvel, J. A m . Chem. Soc,, 55, 345(1933).
65. Frank Orlandi, personal eonsnunication.
66. H. I. Waterman and H. A. Van Westen, Rec. trav. Chim. 48,637 (1929).
67. A Jena, Ann., 155, 80 (1870).
68. R. L. Shriner, R. Fuson, and D. Curtin, "The SystematicIdentification of Organic Compounds," John Wiley and Sons, New York, N. Y., 1956, p. 278.
69. Spectrum No. 1938.
70. J. W. Bruhl, Ann., 235, 8 (1886).
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73. R. Shriner, R. Fuson, and D. Curtin, op. cit., p. 317.
74. I. Heilbron, op. cit., Vol. 1, p. 7.
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SELECTED BIBLIOGRAPHY
Briegleb, F. and Geuther, A. "Ueber das Stickstoffmagnesium and die Affinitaten des Stickgases zu Metelien," Annelen der Chemie und Pharmacie, CXXIII (1892), 228-241.
Emmerling, 0. "Zur Kenntniss des Stickstoffmagnesiums," Bericbte der Deutschen Chemischen Gesellschaft, XXIS (1896), 1635.
Fichter, F., Girard, P., and Erlenmeyer, H. "ElectrolytischeBindung von komprimiertem Stickstoff bei gewohnlicher Temperature," Helvetica Chimica Acta, XIII (1930), 1228-1236.
Koenig, P., Blanchard, E., Morris, J., and Mason, P., "Applications of Metal Nitrides in Organic Syntheses," Journal of Organic Chemistry, XXVI (1961) 4777.
Masdupuy, E. and Gallais, R. "Lithium Nitride," Inorganic Syntheses, IV (1953), 4-7.
Mellor, J. W. A Comprehensive Treatise on Inorganic andTheoretical Chemistry. New York: Longmans, Greene and Co.,1928. VIII, pp x 1110.
Moeller, T. Inorganic Chemistry. New York: John Wiley and Sons,1952. pp ix 966.
Moissan, H. Preparation et proprietes de l'azoture de Calcium," Bulletin de la Societe Chimique, XXI (1899), 881-885.
Ouvrard, L. "Sur un Azoture de lithium," Cocrptes readus de l ’Academie des Sciences, LXIV (1892), 120.
Paschkowezky, S. "Ueber die Darstellung von Magnesiumstickstoff," Journal fur Praktische Chemie, XLVII (1893), 89-94.
Smits, M. A. "Sur l’azoture de Masnesium," Recueil des Travaux Chimiques des Pays-Bas, XII (1893) 198-202.
Szarvasy, E. "Ueber die Einwirkung von Methyl Alkohol aufMagnesiumnitrid," Berichte der Deutschen Chemischen Gesellschaft, XXX (1897), 305-309.
Zintl, E. and Brauer, G. "Konstitution des Lithiumnitrids," Zeithschrift fur Eleclctrochemie, XLI (1935), 102-107.
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V IT A
Perry S. Mason, Jr. was b o m October 2, 1938 in Lubbock,
Texas. Ke attended Vollentine Elementary School in Memphis,
Tennessee through the second grade, then transferred to Harding
Elementary School and Academy in Searcy, Arkansas. He was
graduated from Harding Academy in June, 1955.
The following September, he enrolled in Harding College
and in May, 1959, was awarded a Bachelor of Science with honors
in Chemistry and Mathematics. That summer, he enrolled in the
Graduate School at Louisiana State Ifaiversity, and began teaching
in the fall semester as a graduate assistant in the Department of
Chemistry.
In June, 1960 he married the former Mary Lynn Merrick
of Little Rock, Arkansas.
In addition to holding a teaching assistantship, he has
been a research assistant and, for the last two years, a National
Science Fellow. He is a member of the American Chemical Society
and Phi lambda Upsilon honorary chemical society. At present he
is a candidate for the Doctor of Philosophy degree.
52
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EXAMINATION AND THESIS BEPOET
Candidate: Perry S. Mason, Jr,
Major Field: Chemistry
Title of Thesis: Reactions of Lithium Nitride With Some Unsaturated Organic Compounds
Major Professor ani
Dean of the Graduate School
EXAMINING COMMITTEE:
~ 5 V . \ V W
J.L.B. Et-'l
Date of Examination:
July 30,1963
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