C.?Additive compounds of trinitrobenzene
10
ADDITIVE COMPOUNDS OF TRINITROBENZENE. 1339 c1 .-Additive Compounds of Trinitrobe nxene By JOHN JOSEPH SUDBOROUGH. IN continuation of the investigations on the capacity of polynitro- aromatic compounds to form additive derivatives (compare T., 1901, 79, 522; 1903, 83, 1334; 1906, 89, 583; 1910, 97, 773; 1911, 99, 209) the compounds enumerated in tables I-IV have been pre- pared. During the progress of this work descriptions of a few additive compounds of aromatic hydrocarbons with polynitro-compounds have appeared. Kremann (Monatsh., 1911, 32, 609) has described a compound of trinitrobenzene with fluorene in the molecular pro- portions of 3 to 2, and A. Buguet (Compt. rend., 1909, 149, 857) has prepared compounds of s-trinitrobenzene with phenanthrene Published on 01 January 1916. Downloaded by University of Windsor on 19/10/2014 06:28:13. View Article Online / Journal Homepage / Table of Contents for this issue
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Transcript of C.?Additive compounds of trinitrobenzene
ADDITIVE COMPOUNDS OF TRINITROBENZENE. 1339
c1 .-Additive Compounds of Trinitrobe nxene By JOHN JOSEPH SUDBOROUGH.
IN continuation of the investigations on the capacity of polynitro- aromatic compounds t o form additive derivatives (compare T., 1901, 79, 522; 1903, 83, 1334; 1906, 89, 583; 1910, 97, 773; 1911, 99, 209) the compounds enumerated in tables I-IV have been pre- pared.
During the progress of this work descriptions of a few additive compounds of aromatic hydrocarbons with polynitro-compounds have appeared. Kremann (Monatsh., 1911, 32, 609) has described a compound of trinitrobenzene with fluorene in the molecular pro- portions of 3 to 2, and A. Buguet (Compt. rend., 1909, 149, 857) has prepared compounds of s-trinitrobenzene with phenanthrene
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1340 SUDBOROU~H :
and acenaphthene, the compounds consisting of equimolecular quan- tities of the components.
The compounds characterised by an asterisk could only be obtained by using an excess of the hydrocarbon or base. I n all the other cases the products were prepared by using theoretical quantities of trinitrobenzene and of hydrocarbon or base and crystallising from a suitable solvent, usually alcohol, but occasion- ally benzene. I n the case of paminobenzophenone a mixture of benzene with a little alcohol was used, and with the diethyl- phenylenediamines, a mixture of benzene and light petroleum.
co?lclzcsio?zs.
(1) One of the most interesting facts established is that aromatic hydrocarbons form additive compounds with trinitrobenzene in much the same manner that they do with picric acid. Many of these compounds are comparatively stable, and can be crystallised from suitable solvents. As a rule the colour of these additive compounds is not so marked as the colours of the corresponding amino- or hydroxy-derivatives. It will be noticed that the colour of the hydrocarbon additive compounds is usually yellow, with the exception of the compound with anthracene, the colour of which is bright red.
I n a previous communication (T., 1910, 97, 780) it was sug- gested that the formation of additive compounds from aromatic amines, phenols, phenolic ethers, and sulphur compound: could probably be attributed to the latent valencies of the nitrogen, oxygen, or sulphur atoms. The isolation of stable compounds of hydrocarbons with trinitrobenzene raises the question as to whether in all cases the addition may not be of the same type and be due to the unsaturated character of the aromatic nucleus present.
It is hoped that a study of the ultraviolet absorption spectra of some of these compounds may throw some light on this question.
It is well known that quinones form coloured additive compounds with phenols and aromatic amines, and Pfeiffer has shown recently ( A i z r d e n , 1914, 404, 1) that phenolic ethers and aromatic hydro- carbons, such as durene and hexamethylbenzene, also form coloured additive compounds with chloranil. From this Pfeiffer concludes that the addition is not due to the presence of the amino-, substi- tuted amino-, or hydroxy-group present in the amine or phenol, but is due t o the unsaturated aromatic nucleus, each carbonyl group being able t o satisfy the latent valencies of one benzene nucleus, and he represents such additive compounds by the following type of formula :
@,Me6 . . . O:C6H4:0 . . . C,Me,.
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ADDITIVE COMPOUNDS OF TRINITROBENZENE. 1341
It would appear probable that the formation of compounds between polynitro-aromatic compounds on the one hand and aro- matic hydrocarbons, amines, phenols, phenolic ethers, and sulphur compounds on the other is due to latent valencies of the nitro- groups and of the aromatic residues of the hydrocarbon, phenol, or amine (compare Pfeiffer, Zoc. cit., p. 13). The hydroxy-, alkyl- oxy-, amino-, and alkylamino-groups act mainly as auxochromes, but a t the same time tend to increase the stability of the additive compounds.
On Pfeiffer's scheme these additive compounds are represented as follows :
C,HdNO,), - * * C,"H*. C,H,(NO,), . . . C,,H,*OH. C,H3(N0,)3 . . . C,,H7*NH,.
(2) The question of the number of molecules of trinitrobenzene with which one molecule of the aromatic compound can combine is of considerable importance. An examination of the various addi- tive compounds prepared by Somerhoff (Diss., Zurich, 1904) and the present author tends to prove that the number of molecules of trinitrobenzene does not vary with the number of amino-, substi- tuted amino-, hydsoxy-, or alkyloxy-grovps present, but rather with the number of aromatic nuclei. I n this connexion a condensed system of several benzene or of benzene and heterocyclic rings has to be regarded as a single nucleus.
The following substances form additive compounds of the type one moleculel of trinitrobenzene with one molecule of the sub- stance : The hydrocarbons naphthalene, anthracene, phenanthrene, acenaphthene, chrysene, and retene, ; aniline, its homologues and substituted derivatives ; mono- and di-alkylated anilines ; naphthyl- amines, their alkyl derivatives and substitution products ; naph- thols and alkylated naphthols ; phenylenediamines, tolylenediamines, and naphthylenediamines ; triaminotoluene ; phenylhydrazones derived from aliphatic ketones ; quinoline, isoquinoline, their tetra- hydro-derivatives, and substituted amino- and hydroxy-derivatives ; methylindole, phenylpyrazolones.
The following groups of substances form additive compounds of the type two molecules of trinitrobenzene with one molecule of the substance : Hydrocarbons containing two benzene nuclei, for example, s-diphenylethane, stilbene, tolane, dihydroanthracene, a-dinaphthylmethane, and their amino-derivatives, for example, di- aminostilbene, aminodiphenylmethane, and diaminodiphenyl- methane. Aromatic secondary amines, for example, diphenyl- amine, phenyl-a- and -p-naphthylamines, aa- and BB-dinaphthyl- amines, various tolylnaphthylamines. Derivatives of aromatic
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1342 SUDBOROUGH :
ketones, for example, tetramethyldiaminobenzophenone. Phenyl- hydrazones derived from aromatic aldehydes or ketones, for ex- ample, benzaldehydephenylhydrazone, cinnamaldehydephenylhydr- azone, acetophenonephenylhydrazone. Esters containing two or more benzene nuclei, f o r example, benzyl salicylate, quinol disalicyl- ate. Benzylidene compounds containing two aromatic nuclei, for example, distyryl diketone ; benzylidene 8-naphthylamine. Phenolic ethers containing two aromatic nuclei, for example, phenylnaphthyl ethers and dinaphthyl ethers. Azo-compounds, f o r example, di- methylaminoazobenzene, aminoazonaphthalene. Certain sulphur compounds containing two benzene nuclei, dimethylaniline disul- phide, o-diaminodiphenyl disulphide, 1-phenylbenzothiazole,
C, H4<;>CPh.
There are, however, various exceptions to these generalisations : (a ) Several compounds form additive compounds of two different
types. Thus p hen yl-P-nap h t hylamine, asarone (trime thoxypropenyl- benzene), and tetramethyldiaminobenzophenone can give compounds containing equimolecular quantities of the componentx and also compounds containing two molecules of trinitrobenzene to one of amine.
( b ) Quite a number of s’ubstances containing two or more inde- pendent aromatic nuclei form compounds with trinitrobenzene in the molecular proportions one to one. Among such substances may be mentioned : l-benzeneazo-2-naphthylamine, diethylaminobenzylidene- paminomethylaniline, o : o-diaminostilbene, tetramethyl-pdiamino- trip hen ylmet hane, t etramethyldi- aminotriphenylmethane, paraleucaniline, aminobenzophenone, phenyl salicylate, phenyl-a-naphthyl ether, benzylidene-a-naphthyl- amine, m-nitrobenzaldehydephenylhydrazone, aa-diphenylpyridine, acridine and its derivatives, triphenylpyrrole.
( c ) I n a few cases one molecule of trinitrobenzene combines with two molecules of the substances, for example, carbostyril, dibenzyl- aniline, and n aphthionic acid. The additive compound of trinitro- benzene and fluorene has the molecular ratio 3 : 2. (4) The auxochrome effect of amino- and hydroxy-groups is well
observed in the case of quinoline and its derivatives. Quinoline itself gives an additive compound which is almost colourless, whereas the hydroxyquinolines give yellow o r brown additive compounds and the aminoquinolines give stable, red, crystalline compounds. The auxochrome effect of an ethylene linking is also observed in the case of stilbene. Thus s-diphenylethane gives a very pale yellow-coloured additive compound, and the unsaturated analogue
Both series of compounds are stable. 8
t e trame thyldiaminobenzh ydrol,
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ADDITIVE COMPOUNDS OF TRINITROBENZENE. 1343
stilbene a deep canary-coloured compound. Tolane also yields a deep yellow-coloured product.
The difference in colour between the additive compounds of trinitrobenzene with anthracene and dihydroanthracene is also marked.
(5) The results show that most naphthalene derivatives form additive compounds with trinitrobenzene, and that the colour of such compounds is yellow unless an auxochrome such as an amino-, a substanced amino-group, or several hydroxyl groups are present. Substituents such as Br, NO,, CN, CO,Et, CHO, Bz do not inter- fere with the formation of additive compounds. Naphthalene deriv- atives containing the SO,*OH or S0,Cl groups, on the other hand, do not appear to form additive compounds with trinitrobenzene.
(6) Pyrrole, its phenyl, tolyl, and triphenyl derivatives all yield additive compounds with trinitrobenzene. The compound with pyrrole has a yellow colour (van Romburgh, Rec . truv. chim., 1895, 14, 67), those with pllenyl- and tolyl-pyrroles a canary yellow colour, and the compound with triphenylpyrrole a purple colour.
(7) Attention has already been drawn (T., 1910, 97, 776) to the difference in colour between the additive compounds of benzene with quinoline derivatives on the one hand and with tetrahydro-deriv- atives of quinoline on the other. Another example is given here, namely, lethyltetrahydroquholine, which forms a black additive compound with trinitrobenzene.
(8) So far i t has not been found possible t o isolate additive compounds of trinitrobenzene with the following substances : Di- phenylmethane, triphenylcarbinol, diphenylfulvene, xanthone, fluorenone, benzil, cinnamylideneacetic acid, resorcinol dimethyl ether, p-dihydroxydiphenylmethane, ppdiphenol, naphthalene- sulphonjc acids and- sulphonyl chlorides, acetyl-pphenylenediamine, benzamidine, piperazine, antipyrine, phenacetin, strychnine, bornyl- amine.
I n conclusion, I have to t,hank Messrs. S. H.. Beard and R. Rungaswamy Naidu for valuable assistance in the analytical portion of the work.
GENERAL AND ORGANIC CHEMISTRY LABORATORIES, INDIAN INSTITUTE OF SCIENCE,
BANGALORE. [Received, August 15th, 1916.1
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TA
BL
E I.
Add
itiv
e C
ompo
unds
of
Aro
mat
ic R
ydro
carb
ons with
s-Tr
initr
oben
zene
. M
ols.
of
nitr
o-co
m-
i-,
w
rp
tp
Com
pone
nt.
8-D
iphe
nyle
than
e ...
......
......
...
Stilb
ene
........
........
........
......
Tol
ane
........
........
........
........
. N
apht
hale
ne ....
........
........
....
B -M
ethy
lnap
htha
lene
...
......
...
Ant
hrac
ene
........
........
........
D
ihyd
roan
thra
cene
...
......
......
D
ibro
moa
nthr
acen
e ...
......
......
Ph
enan
thre
ne
........
........
.....
Fluo
rene
......
........
........
........
A
cena
phth
ene
........
........
.....
Ace
naph
th y
lene
.......
........
......
Chr
ysen
e ....
........
........
........
.. R
eten
e ....
........
........
........
.. a -
Din
aph t
hylm
e tha
ne ...
......
...
poun
d to
m
ols.
of
hydr
o -
carb
on.
2:l
2
:l
2:
l
1:l
1:l
1
:1'
2:
l
1:l
1:l
3:2
1
:l
1:l
1:l
1:
l
2:l
Ana
lysi
s.
Form
ula.
A
ppea
ranc
e.
M.
p.
C,6
H,o
Ol,N
6 P
ale
yello
w c
ryst
als
102"
C
,,H,,0
,,N6
Wel
l dev
elop
ed,
cana
ry c
ryst
als
120
Lus
trou
s de
ep
yello
w,
quad
rati
c)
C26
H16
012N
6 {
slat
es
,- 96
Cl,H
,,0,N
3 P
ale
yello
w n
eedl
es
152.
6 C
,,H,,0
,N3
Can
ary
yello
w n
eedl
es
123
C.&
,H13
O,N3
Sc
arle
t ne
edle
s 16
4
C,,,H
llO,N
3Br,
Fea
ther
y re
d ne
edle
s 17
9 C
,oH
130,
N3
Glis
teni
ng o
rang
e ne
edle
s or
pla
tes
158
Cl8
H,,O
,N3
Gol
den-
yello
w n
eedl
es
168
C,4
Hl,0
,N,
Can
ary-
yello
w n
eedl
es
186
C,H
,,O,,N
, B
righ
t ye
llow
, gl
iste
ning
pla
t,es
141.
5
C,,H
180,
,N,
Yel
low
nee
dles
92
-92.
5
C44H
,gO#g
G
olde
n-ye
llow
pla
tes
-
C18
H,,0
6N3
Gol
den-
yello
w n
eedl
es
221
C,4
H,I0
,N3
Yel
low
nee
dles
13
9-14
0
Fou
nd
per
cent
. N
= 1
3.80
N
= 1
3-91
N=
13.
97
N=
12.
31
N=
11.
9 N
= 1
0.92
N= 13
.8
Br =
28.8
N
= 1
0.84
N
= 1
3.1
N=
ll*
9
N=
12.
0 N
=
9-62
N
=
9.45
N
= 1
2.24
Cal
cu-
late
d pe
r ce
nt.
13.8
1 13
.86
13-9
1
12.3
2 11
.83
10.7
4 13
.86
29.1
10
.74
13.0
11
.4
11.5
9.
52
9.40
12
-10
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TA
BL
E 11
.
A d
di t iv e
C
o m pounds
of N
u ph t I
mle
n e D
eriv
a t iw
e s
wit
h s- T r
iizi
t r o
b e I i
z e IZ
c .
Mol
s. of
tr
init
ro-
benz
ene
to
Mol
s. of
na
ptha
-len
e F
orm
ula.
C
ompo
nent
. de
riva
tive.
a-
Bro
mon
apht
hale
ne
......
......
1
: 1
a-D
ibro
mon
apht
hale
ne
......
...
1 : 1
a-N
itro
naph
thal
ene
..,. . ..
.....
1 :
1
"a-N
apht
honi
tril
e ,..
......
......
...
1 : 1
B
-Nap
htho
nitr
ile
. . .. . . . .
. . . . . . .
. . .
1 :
1 *a
-Nap
htho
ic a
cid
......
......
...
1 :
2 M
ethy
l a-n
apht
hoat
e .....
......
....
1 :
1 M
ethy
l p-n
apht
hoat
e ...
......
...
1 : 1
a-N
apht
hyl
met
hyl
keto
ne ...
...
1 : 1
Phe
nyl
a-na
phth
yl k
eton
e ...
...
1 : 1
&N
apht
hola
ldeh
yde ...
......
......
1
: 1
a-N
apht
holp
htha
lein
. . . . .
. . . . . .
. . . .
1 :
1
1 : 3
-Dih
ydro
xyna
phth
alen
e . , .
. . .
1 :
1
Eth
yl n
apht
hylc
arba
mat
,e . . .
. . .
1 :
1
*aa-
Azo
naph
thal
ene ...
.... . ..
.....
2 :
1 a
-Am
inoa
zona
phth
ylen
e . . .
. . . . . .
2 : 1
4-A
min
o-1-
naph
thyl
eth
yl e
ther
1 : 1
4-Acetylamino-1-naphthyl ethy
l )
1:l
et
her
Ana
lysi
s.
* /h
_
tJ
Cal
cu-
Fou
nd
late
d 8
App
eara
nce.
31
. p.
per
cent
. pe
r ce
nt.
4 C
l,Hlo
06N
3Br L
emon
-yel
low
nee
dles
C
,,H,0
,N3B
r, L
emon
-yel
low
nee
dles
C
16H
,00,
N4
Pal
e ye
llow
, pri
smat
ic n
eedl
es
Cl,H
lo0,
N4
Pal
e ye
llow
cry
stal
s C
1,H
lOO
,N4
Pal
e ye
llow
cry
stal
s C2
,H,,O
10N
3 P
ale
yello
w n
eedl
es
C18
H13
08N
3 P
ale
yello
w n
eedl
es
C18
H13
08N
3 P
ale
yello
w n
eedl
es
C,,H
130,
N3
Sulp
hur-
yello
w n
eedl
es
C23
H15
0,N
3 P
ale
yello
w n
eedl
es
Cl,H
l10,
N3
Fea
ther
y-br
own
need
les
c H
0
N
C,,H
,,OB
N3
Bri
ck-r
ed n
eedl
es
C,,H
l,08N
4 C
anar
y-ye
llow
nee
dles
C
3,H
,001
2N8
Rus
set-
brow
n ne
edle
s C
32H
2201
2N9
Bri
llia
nt b
lack
nee
dles
C
1,H
1,O
,N4
Glis
teni
ng p
urpl
ish-
blac
k ne
edle
s
C20
H1,
0,N
4 B
righ
t re
d ne
edle
s
Wel
l de
velo
ped
brow
nish
-yel
low
34
21 10
3 1 c
ryst
'als
137"
15
3 73
-73 88
95
182.
5 10
7 10
4.5
112
89
137
I23
5
174.
5 91
-5-9
2 19
8 23
2-23
3 17
7.5
156.
5
N=
10.
15
Br =
32.0
N
= 1
4.45
N
= 1
5.26
N
= 1
5.35
N
=
7.7
N=
10.
56
N=
10-
54
N=
ll.O
N
=
9.38
N
= 1
0.77
N=
6.
7
N=
ll-1
1
N=
13-
08
N=
16.
41
N=
17.
2 N
= 1
4.0
N=
12.
7
10.0
0 32
.1
14.5
1 15
.30
15.3
0 7.
6 10
.53
10-5
3 11
.0
9.43
10
-91
6-66
11.2
6 13
.08
15.8
2 17
.40
14.4
7
12.9
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TABL
E 111.
Add
itiv
e C
orn
po
ds
of
s-Tm
'nitr
oben
zene
wit
h C
yclic
Bas
es a
nd w
ith
som
e B
enze
ne D
eriv
ativ
es.
Mol
s. of
ni
tro-
com
- po
und
to
Mol
s. o
f A
.-Ben
zene
de
riva
tive
s.
amin
e.
*p-A
min
oben
zoph
enon
e ....
.....
1 :
1
*Dib
enzy
lani
line
......
......
......
1 : 2
Eth
yl 3
: 5-
diam
inob
enzo
ate
...
1 :
1
*Diethyl.m-phenylenediamine ...
*D
ieth
yl-p
-phe
nyle
nedi
amin
e 1
:l
I
o-D
iani
sidi
ne ...
..........
..........
. 2 : 1
3 : 6
-Dia
min
oani
sole
......
......
...
1 :
1
p-A
min
odip
heny
lam
ine
......
...
2 :
1 A
min
odip
heny
lmet
hane
....
.....
2 : 1
D
iam
inod
iphe
nylm
etha
ne ...
......
2 : 1
Dim
ethy
lam
inoa
zobe
nzen
e ...
......
2 : 1
2 : 4
-Bis
benz
enea
zoph
enol
...
...
2 : 1
Para
leuc
anili
ne ...
..........
........
1 :
1
2-A
min
o-1-
naph
thyl
eth
yl e
ther
1 :
1
Eth
yl phloroglucinoldicarboxylate
1 :
1
2 : 1
Phe
nyl c
inna
myl
iden
emet
hyl
Dis
tyry
l di
keto
ne ..
......
......
....
Pipe
rine
....
........
........
........
.. 1 :
1
Eth
yl p
iper
ate
..........
..........
.
} 1
:l
keto
ne
-
App
eara
nce.
D
ark
yello
wis
h-br
own
pris
ms
Dar
k ru
by-r
ed p
rism
s B
righ
t br
ick-
red
plat
es
Pru
ne - co
lour
ed p
rism
s B
luis
h-bl
ack
need
les
Fla
t bl
ack
need
les
Dar
k re
ddis
h-br
own
need
les
Bla
ck p
late
s B
rick
-red
pri
sms
Dar
k br
own,
fia
t pr
ism
s P
rune
-bla
ck p
rism
s R
eddi
sh-b
lack
pla
tes
Gol
den-
brow
n pl
ates
P
urpl
ish-
blac
k ne
edle
s P
ale
yello
w n
eedl
es
Sul
phur
- yel
low
nee
dles
Lem
on-y
ello
w p
late
s
Sca
rlet
, pri
smat
ic n
eedl
es
Ora
nge-
red
need
les
M. p
. *1
1°
86-8
7 13
9 88
.5
79
144
130
105.
5 66
-67
132-
5 14
0 13
5.5
125
177.
5 76
12
5
108
130
90-9
1
Ana
lysi
s.
&
Fou
nd
per
cent
. N
= 1
3-85
N
=
9.5
N=
18.
2
N=
19.
0 N
= 1
6.6
N=
20-0
N
= 1
8.5
N=
16.
4 N
= 1
8-2
N=
16.
8 N
= 1
9.7
N=
19.
0 N
= 1
4.5
N=
8.
8 N
= 1
2.65
N=
10.
1
N=
ll*
3
-
-
Cal
cu-
late
d pe
r ce
nt.
13.6
6 9.
2 17
.8
-
18.6
$
16.7
W
0
19
.9
7d
18.5
16
-1
2 .. 18
.0
16.7
19
-4
19.2
14
.0
8.7
12.7
9.4
11.2
Publ
ishe
d on
01
Janu
ary
1916
. Dow
nloa
ded
by U
nive
rsity
of
Win
dsor
on
19/1
0/20
14 0
6:28
:13.
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TA
BL
E 11
1.
Add
itiv
e C
ompo
unds
of
s-Tr
initr
oben
zene
wit
h C
ycli
c B
ases
and
w
ith
som
e B
enze
ne D
eriu
ativ
ea
(con
tinue
d).
Mol
s. of
ni
tro-
com
- po
und
to
B.-C
yclic
N
itrog
en C
ompo
unds
, M
ols
of
4-A
min
oqui
nolin
e ...
......
......
...
2-A
min
oqui
nolin
e ...
......
......
...
Car
bost
yril
........
........
........
... 1-Ethyltetrahydroquinoline
...
*Phe
nylp
yrro
le ..
..........
.........
"Tol
ylpy
rrol
e .....
..........
.........
Met
hyla
crid
ine
..........
..........
. Ph
enyl
acri
dine
.....
..........
......
Dip
heny
lpip
eraz
ine
........
.......
3-A
min
ocar
bazo
le ...
........
.......
3-A
cety
lam
inoc
arbe
zole
....
.....
3 : 5
-Dip
heny
lpyr
azol
e ....
........
h
ino
stry
chn
ine
........
........
..
Tri
p hen
ylp y
rrol
e ...
......
......
...
amin
e.
1:l
1
:2
1:l
1
:l
1:l
1:l
1
:l
1:l
2
:l
1:l
1
:l
2:l
2
:l
1':
1
App
eara
nce.
R
uby-
red
pris
ms
Bri
ght c
rim
son
need
les
Sulp
hur-
yello
w n
eedl
es
Bla
ck n
eedl
es
Can
ary-
yello
w n
eedl
es
Can
ary-
yello
w p
late
s P
urpl
e ne
edle
s G
reen
ish-
yello
w n
eedl
es
Dar
k ru
by-r
ed p
rism
s R
uby-
red
plat
es
Pur
plis
h-bl
ack
plat
es
Dark re
d ne
edle
s Su
lphu
r-ye
llow
pri
sms
Red
nee
dles
M. p
. 11
1"
186
178
70-7
1
80
77
1 3 6.
5-1
37
12&
-120
*5
139.
5 17
1 19
5 19
3.5
135.
5 16
1
Ana
lysi
s.
&
Fou
nd
per
cent
. N
= 1
9.7
N=
19.
9 N
= 1
3.8
N=
16.
0 N
=15
.96
N=
15.
26
N=
ll*
27
N
= 1
3.8
N=
12.
0 N
=16
*9
N=
17.3
5 N
= 1
6.15
N
=17
*6
N=
16.
45
Cal
cu-
late
d pe
r ce
nt.
19.6
19
.6
13.9
15
.0
15.7
3 15
.14
11.0
2 13
.8
12.0
16
.9
17.7
16
-02
17.3
16
.3
Publ
ishe
d on
01
Janu
ary
1916
. Dow
nloa
ded
by U
nive
rsity
of
Win
dsor
on
19/1
0/20
14 0
6:28
:13.
View Article Online
TAB
LE IV
. A
ddit
ive
Com
poun
ds o
f so
me
Aro
mat
ic S
ulph
ur C
ompo
unds
wit
h s-
Tm'n
itrob
enzc
ne.
Mol
e. O
f ni
tro-
com
poun
d to
mol
s. o
f su
lphu
r C
ompo
nent
s.
com
poun
d.
Form
ula.
T
hion
apht
hol .....
..........
.........
1 :
1
C16
Hl1
06N
,S
Dith
iore
sorc
inol
.........
..........
.. 1 :
1 C
12H
,06N
3S,
1-Ph
enyl
benz
thia
zole
....
........
2 : 1
C,,H
l50,
N,S
Dim
ethy
lani
line
disu
lphi
de ..
....
2 : 1
C,,H
,,O,N
,S,
0-D
iam
inod
iphe
nyl d
isul
phid
e .
2 : 1
C,,H
,,O,N
,S,
Thi
odip
heny
lam
ine
........
.......
1 :
1 C
l,H,0
6N,S
Ana
lysi
s.
&
Fou
nd
Cal
cu-
Per
late
A
ppea
ranc
e.
M. p
. ce
nt.
per
cent
. B
righ
t yel
low
nee
dles
15
" N
= 1
1.47
11
.26
Bri
ght y
ello
w c
ryst
als
76-7
7 S=
18.0
2 18
.03
Glis
teni
ng y
ello
w n
eedl
es
106
N=
15.
49
15.3
8
Dee
p pr
une-
colo
ured
nee
dles
97
.5
N=
15.
50
15-3
3
Dark
bri
ck.r
ed n
eedl
es
100
N=
16-
71
16.6
2
Bla
ck n
eedl
es
124.
5 S
=
7.46
7.
77
Publ
ishe
d on
01
Janu
ary
1916
. Dow
nloa
ded
by U
nive
rsity
of
Win
dsor
on
19/1
0/20
14 0
6:28
:13.
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