C.hapfer . .

Synthesis of cyanoamidinosubstitutedthiocarbamides (5), 1,3-diformamidino-

thiocarbamide (6) and N-substitutedformamidinoformamidinothiocarbamides (6)

Chapter I

Cbaptcr - t
Synthes is of Cyanoamidinosubstitutedthioca rbamides (5),

1.3-difo rmamidinothiocarbamide (6) and N-substitutedformamidin oformamidin othiocarba mides (6)

Abstract
interaction of cyanoguanidine ( I) with phenylisothiocyanatc (2a)
p -Cl-phenyli sothiocyanatc (2d), p -tolyl-isothiocyanate (2c), methyli sothiocyanate (2d), ethylisothiocyanate (2e) and 1-butylisothuiocyanate (2f) and also
with thiourea (3a) phenylthiourea (J b), mcthylthiourea (3c), elhyltJ1iourea (3d)
and allylthiourea (3e) in presence of hydrochloric acid in acetone-ethanol
medium have been reinvestigated, the products isol ated in these reacti ons
were characterised on the basis of conventional eleme ntal analysis, chemical
charncterestics and through IR and NM R spectral studies.

lntrod uction
Cynnoguanidine has been briefly studied by many

r~searchers .

It is an important organ ic compound for its pharmacological, medicinal ,

biological, agricultural and industrial applications. 12 Cyanoguan1dine is a

bifunctional molecule. It has basic formamidino group at position 3 and a
cyano/nitrilo group at position 1. This molecule, therefore, is expected to
produce varities of certain interesting heteroacyclic and heterocyclic nitrogen,
nitrogen and sulphur containing organic compounds, tl1rough its reactive basic
a m ino gro up and cya no gro up. As evid en t from th e s tru ct ure of
cyanoguanidine, it is quite likely that cyanoguanidine which is having basic
fonnamidino group react with various isothicyanates to produce related
cyanoamidino-substitutedthiocarbamides (5). T hi s reaction is akin
reac ti o n of pare nt guanidin e and

isothiocyanate s3 4

10

the

111 wh ich re late d

amidinothicarbamides were formed. Cyanoguanidine also has cyanamide like

s tructure. Interact ion of cyanamide and vari ous thi o ureas have been

R C Panpalia, Ph'.> Thooos

50

ChaptM

investigated in sufficient details.s- The initial product of this reaction was

shown lo be mono-formamidinomonosulphide salt, which was found lo be

readily rearranged into an amidinothiocarbamide salts. A ll these compounds
possess medicinal, pharmacological, agricultural and industrial values.
Therefore, it appeared interesting to reinvesltgalc the reactions
of cyanoguanidine with different isotluocyanates in section-A. While sect1onB comprises interactions of cyanoguanidine with different thiourea to isolate

cyanoam i di no s ubs ti luted th iocarbam ides a net

l , 3-di form am id i no-

thiocarbamides and N-substituted fonnamidinoformamidino1hiocarbamides

respectively which were used as intermediate in the synthesis of biurets and
Hector's bases. With the above objectives the interactions of cyanoguanidinc
has been carried out. The mechantsm of formation of products are as fol lows.
,.Jl

'<C' - '<H - C - N ,

II

II

NH
(I)

Where R =

NC - NH - C - NH - C - NH - R

Acetone

C = N-R

II

II
S

NH
(2)

(5)

phenyl, p-Cl-phenyl, p-tolyl,

methyl, ethyl, I-butyl

Acetone

112N - C - NH - C = N + HCl ---?

II

'IH

~N-C - NH - CJ~ ~~ - C-NH - R

II
II ...
II
NH

NI I

(I)

+"

NH

(3)

Acetone

11,N - C

II

NII

NH - C - NH - C - NH - R

II

11

NII

Aqueous
~

NnllCO,

H2N- C -

NH - C -

NH

NH

(6)
Where R = Ii, methyl, ethyl, allyl, phenyl

(Scheme - I)

II

II

S- C - NH - R]
II

NH

Chaptei - I

Res ults and Discussion

Section - A
Cyn noamidinomethylthiocarbamide (Sd) :
Interaction o f cyanoguani dine ( I ) was carried oul with
melhyli sothiocyanate (2d) in acetone medium on water bath for 6 hours. It
was filtered in hot condition. The resultant filtrate was evaporated on room
condition. Needle shaped yellowish crystals were isolated. Yield 74% m p.
I83C.

Properties of (Sd) :

I.

The compound is lemon yellow colour crystalline solid having m.p.

183C

2.

It contained nitrogen and sulphur elements.

3.

Desulphurised with alkaline plwnbite solution.

4.

The Rf value was found to be 0.4, for dimrnne as solvcnl on silica

gel-G plate with layer thickness of 0.3 mm.

Elemental analysis
Found

Calculated

29.85

30.57

Hydrogen

3.95

4.45

Nitrogen

44.43

44 .58

Sulphur

20.3 8

20.38

Elements
Carbon

From the analytical data the molecular formula was found to be

C4 H7 N5S.
7

IR Spectrum: The IR spectrum was carried

0 111

in KBr pellctes and

reproduced on Plate No. IR-1 . I The importan1 absorption can be

correlated as follows.

:-.~

Plait No. IR- 1.1

,'

'
"\11[1\IC'
~
"UU'H"(I ,.,.-t

~I
i

:! u:,:u t:u
. m
1

Platt No. PMR- 1.1

'~
~m:
I lU.tU
"llPt
~'

. Ht

l.t

"..: ...~Jm
a

,~

;:

,."..'

.~:.': :

* Jt
Cf

r1
ff

Ht.I:

1.1n.
.UC

'"u
11.nt
ffUOI
.Ut
,_, un.n

Chapter I

Assignment

Absorption observed

Absorption expected
(cm')

(cm')

8.
9.

1080

> C = S stretching

1360

N> C = S groupmg

1380-1 050 10

1660

> C - N H (imino)

1789-14 7 111

2850

C - N aliphatic

2940-27 10"

1200-1 0509

It formed picrate mp 163 C.

PMR : The PMR spectrum was carried out in C DCl1+ DMSO-d, arc
reproduced on Plate No. PM R- 1. 1. The important chemical shirts can be
mte'llreted as follows This specttum distinctly displayed signals due to
- C H1 protons at

o 1.5 ppm and NH protons at o7.2-7.3 ppm.

From the above properties and spectral analysis the compound

(5d) was assigned the structure as cyanoamidmornethy lth1ocarbamide.
NC - NH - C - NH - C - NII - CH,

II

II

NII

(5d)

Similarly, cyanoamidinophenylthi ocarba mide (5 a). cyanoam1d1110-p -Cl-phe11yl1hiocarbamide (5b), cyanoamidino-p-1olyl1hiocarbam1de

( 5c ). cya n oam1d i noe thyl1hio ca rbarn id e (5c) and cy an oamidino-1butyhh1carbamide (5r) were prepared by interacllon of cyanoguamdine with
phe nyh sothiocynate (2a). p -Cl-phe nylisoth1ocyna1e (2b). /Holy lisoth1ocyna1e
(2c). e1hy lisoth1ocynate (2e) and /-bui 1. ti .
.
y tso 11ocynate (2r) Ill acelone medium
respeCtJvely by the a bove me ntioned method in Experunent No ., t 6 . d
0
listed 111 Table- I.
an

R C Panpol~. f'll O Thes.s

53

Chapter I

Table - 1

Sr. Expt.
No. No.
I.

2.

3.

4.

5.

Yield ('Y.)

m.p. C

82

187

.. p-Cl-phenyl .

61!

147

... p-tolyl .......

61

163

... ethyl

78

179

. /-butyl

72

182

Cyanoamidinosubstitutedtbiocarbamide
phenyl ..

*Gave satisfactory C, H, N, and S analysis.

Section B
II Synthesis of 1,3-diformamidinothiocarbamide, hyd rochloride (6a)
(i)

Inte r action of cyanogua nidine and thioure:i in presence of aqueous

hydrochloric acid in acetone medium :
Interaction ofcyanoguanidine ( I) with thiourea (3 a) in presence

of aqueous hydrochloric acid was carried out in acetone medium , duri ng

boiling the suspended cyanoguanidin e went into the solution and a new product
was found to be gradually separated out. It was filtered in hot condition and
c1ysta llized with aqueous ethanol to get (6a), m.p. 265-66C(d).
(ii)

Interaction of cyanoguan idine and thiourea in presence of hydrogen

chloride (gas) in acetone and ethe r mixture as medium :
Interaction of cyanoguanidine ( I) was carri ed out with thiourea

(3a). To a suspension of cyanoguanidine and thiourea in e the r and acetone

( I: I) mixture, HCI gas was bubbled for I0 minutes. and the reaction mixture
was re nuxed. The suspe nded cyanoguanidine went into the solution and new

Chapter - I

product was found to be gradually separated out, it was filtered in hot condition
and c1ystallized with aqueous ethanol to get (6a), m .p. 265 -66C(d).
As investigated in the above reactions, the ide ntical product with
m .p. 265-66C(d) has been isolated in (i) and (ii). But in ( ii) yield of product
is more, probable reaction mechanism of format ion of (6a) may be stated as
follows.
C- NH- C"'N

+ HCI

II

H2N-C-NH C=NH

II

NH

NH

Cl

II N - C- NH
i
11
i

(I)
Cyanoguanidine

(3a)

HiN-C- NH- C- Nl-l- C-Nl-12

11
NH

II
S

II
NH . 2HCI

Thiourea

HiN- C- NH-C-U- NH 2
[

(6a)

II

11/'11

NH

NH

NH . 2HCI

Unstable monosulphide

I.J-di formam idinothiocarbamide

hydrochloride
'

Properties of (6a) :
I.

It is pale yellow, crystalline solid, 265-66C(d).

2.

It contained nitrogen, sulphur and chlorine.

3.

It gave effervescence with sodium bicarbonate so it is acidic in nature.

4.

Desulphurised with alkaline plumbite solution .

5.

The Rf value was found to be 0.3 for dioxane as solvent on si lica gel-G
plate with layer thickness of 0.3 mm.

6.

It formed picrate 229C.

7.

Equivalent weight was found to be 23 1.

Elemental analysis :
Elements
Carbon

Found

Calculated

15.29

15 .52

H ydrogen

3.98

4 31

Nitrogen

36. 13

36.22

Sulphur

13.69

13.79

From analytical data the molecular form ul a was fou nd to be

9.

C, H 10N,SCl2 .

I0.

IR Spectrum: The IR spectrum was carried out in KBr pelletes an d is

reproduced on Plate no. IR- 1.2 . The important absorption can be
correlated as fo llows.

Absorption observed
(cm')

11 .

Assignment

Absorption expected
(cm1)

3435.6

N - H stretching

3500-30009

1638. 1

C = N stretching

1789- 14 71 10 11

1523.9

> C = NH (imino)
grouping

1789-14 71 11

11 99.7

C - N stretching

1340- 1250 10 12

991.9

N
N>

1200-1 050 10 12

C ~ S grouping

PMR : The PMR spectrum 12 14 was carried out in CDC13+ DMSO-d,

and reproduced on Plate No. PMR-1 .2 This spectrum distinctly displ ayed
the signal s due to NH protons at Ii 6. 77 ppm .
T he signals at

o 3. 13 ppm is due to moisture in

iS 1.25 ppm is due to DMSO.

DMSO-d,, and

100.00

r.r

D. DD-1----..--

..-- - - . -- - r-

- - r -- - - --..,-- --

--r-

-~

DS/03, 17 12:!56 R. CJSAJr.P.u.oro.

Y: 4 aean1, 4 .0el'l1 , flat , uooth, 1bu

s pl.i::ode:rt:S 4A $'

Plote No. IR- 1.2

(I v -

IPlate No. PMR- 1.2 I

ChaiJler - I

From the properties and spectral analysis the compound (6a)

was assigned the structure as 1,3-diformamidinothiocarbamide. hydrochloride.
H 2N - C-

II
NH

H C'- NH-C-N H2
11
II
S
NH . 2llll
(611)

II I

N "-Phenylformam idinoformamidinotbiocarbamide,
hydrochloride (6b):
Interaction of cyanoguanidine ( I) and phenylthiourca (3 b) was

earned o ut in presence of hydrogen chloride gas

111

acetone-e ther medium. to

obtain sticky brown semisoli d, whic h on trituration sever al times with

petroleum e ther gives (6b), m.p . I R2C .
Properties of (6b) :
It is dark yell ow, crystalline solid. m .p . I 82C
2.

It contained nitrogen. sulphur a nd chlorine

It gave effervescence with sodium bicarbonate.

4.

Desulphuri sed with alkaline plumbite solution.

It formed picrate I72C

Eleme ntal analysis :

Elements
Carbon

Found

Calculated

33.48

35.06

Hydrogen

3.72

4 .5S

Nitrogen

26.84

27.27

Sulph ur

10 21

10.39

Chapl"' I

Fro m analytic al data the molecular fonnula was found to be

7.

C 9H ,~

.sc12 .

IR Spectrum: The IR spectrum was carrie d out in KBr pe\letes and is

8.

reproduced on Plate

o. IR- I .3. The important absorption can be

correlated as follows.
Assignment

Absorption ohserved
(cm')

3373 .9

N - H stretching

3500-30009

3 150.0

C - H(Ar) stretching

3150-3000"

1669.0

1572.4

> C = NH (imino)
grouping

1789- 1471 11

1394.7

C - N stretching

1340- 1250 10 12

11 81.3

N> C = S grouping
N

1200- 105010. 12

C - S stretching

800-600 14

596.6

Absorption expected
(cm')

N stretching

1789-14 7 1' 0 11

PMR: T he PMR spectrum 12 14 was c arried out in CDCl 1 ~ DMSO-d6

and reproduced o n Plate No. PM R- 1.3 This spectrum distinctly displayed

the signa ls d ue to NH protons a t

o3.25-3.27 ppm. ArN H protons al

Ii 7.9-8.0 ppm and Arl l protons at 1i 6.90 ppm

The signals al

o2.55 ppm are due to moisture in DMSO-d and

Ii 1.24 ppm are due to DMSO.

From the properties and spectral a na lysis 1he compound (6b)
was assign ed the s tru ct ure as N" -ph e ny lfor m a m id in ofo rm a m id ino thiocarbamide, hydroc hlo ride.

lDO.DD

%T

A
a

0.001+---~-----,----;------r-----,-----

os103t17 14:40 R. C.tSAlf.P.U.OtD.

,.--

~~

Plate No. ffi- 1.3

X: .- scans, 4'.0c11-1, fht., 11110o\h, 1.bu

sp1 .codur.S7R

'~Cl

~. .

'll1

IPlnte No. PMR- 1.3 j

''

11

Chapler - I

C6H - HN- C-NH - C-NH-C-N H 2

'

II

NH

II

II

NH . 211CI

(6b )

Simi larly, N"-methylformamidinoformam1dinothiocarbamide

hydroch lond e , ( 6c)

"-ethyl formam idinofo rm amidi noth1ocarbam1 de

hydrochl oride (6d) and N"-allylformam idinoformamiclinothiocarbamide

hydrochloride (6c) were prepared by the above mentioned as described in
Expt. No. 9 to I I and listed in Table-2.

Sr.

Expt.

No.

No.

------thiocarbamide, hydrochloride

N"-methylformamidinoformamidino-

Yield(%)

m.p. oc

53

123

62

108

69

203

thi ocarbamide, hydrochloride

2

10

N"-ethylforma1uidinofo1mamidinothiocarbam ide, hydrochloride

II

N"-Allylformamidinoformamidinothiocarbamide, hydroch Jori de

'Gave satisfactory C, H, N, and S analysis.

R C Panpllia, Ph 0 Thesis

59

CNljlter -

Experimental
The melting points of a ll the synthesised compounds were
iccoidcd usmg hot paraffin bath and are uncorrected. The carbon and hydrogen
analysis was carried out on Carlo-Ebra- 11 06 analyser. nitrogen cst1111anon
was earned out on Colman-N-analyscr-29 lR spectra were recorded on Perkin

t ime specirome1er 111 the range 4000-400 c m' 1n KBr pelle1cs. Pf\.IR spectra
were 1ccorded on Bruker AC-300F spectromete r with TMS as interna l standard
using C' DC I, and DMSO-d, as solvent. The purity o f the compounds "as
checked o n S1ltca Gel-G plates by TLC with layer thi ck11css of 0.3 mm All
chenuculs used were of A R grade (India make) excepl allylth io urea I ancaster
(Gc1many make). RN Cs and phenylthiourea has been prepared by a lread}
kno" n methods."

t..xpcri mcnt No. I :

Preparation of cyanoamidinophe nylth iocarbamidc (Sa) :
A mi1'1ure of cyanoguanidine (0 05 M) and phenylisothiocyana1e
(0 O~ M) was re nuxed over a water bath in acetone medium for 4 hours. It
was filtered 1n ho1 conditio n. The resultan t filuat e on evaporatio n gne (Sa ).
yie ld 82%, mp. I 87C.

Expe riment No. 2 :

Prepa ration of cya noamidino-p-Cl-phenylthioca rhamidc (Sb)
A mixture of cyanoguan1d1nc (0 05 M) and p-C'l-pheny ltsotluocyanate (0.05 M) was refluxed over a water bath in aceto ne medium
fo1 4 hours It was filtered

in

hot condition. The resultant filtrate on evaporation

ga\e (5 b). yield 68%, m.p. 147C

Chapte1

Experiment No. 3 :
Prepa r a tion of cyanoamidino-p-tolylthiocarbamide (Sc) :
A mixture of cyanoguanidine (0.05 M ) and p-tolylisothiocyanatc

(0 .05 M) was refluxed over a water bath in acetone medi um for 4 hours. It
was filtered in hot condition. The resultant filtrate on evaporation gave (Sc),
yield 6 1%, m.p. l 63C.

Experiment

o. 4 :

Preparat ion of cyanoamidinomethylthiocarba mide (Sd) :

A mixture of cyanoguanidine (0.05 M) and methyli sothiocyanate
(0.05 M) was refluxed over a water bath in acetone medium for 4 hours. lt
was filtered in hot condition. The resultant filtrate on evaporation gave (5d),
yield 74%, m .p . I 83C.

Expe riment No. 5 :

Preparation of cyanoamidinocthylthiocarbamide (Se) :
A mixture of cyanoguanidin e (0 .05 M) and ethylisothiocyanate
(0 .05 M) was refluxed over a water bath in acetone medium for 4 hours. It
was fil tered in hot condition . The resultan t filtrate on evaporation gave (Se),
yield 78%, m.p . 179C.

Experime nt No. 6 :
Preparation of cyanoamidino-t-butylthiocarbamidc (Sf) :
A mixture of cyanoguanidine (0.05 M) a nd t-butylisothiocyanatc
(0.05 M) was refluxed over a wate r bath in acetone medium fo r 4 hours. It
was filtered in hot condition . The resultant filtrate on evaporation gHve (Sf),

y ield 72%, m .p. 182C.

R C Panpaloa, Ph.O The$<s

61

Chl!>le<. I

Phenylthiourea :
Aniline (52 ml) was taken in 500 ml round bottom nask to it
cone HCI (52 ml) and was added, the reaction mixture "as warmr.d upto the
fonnation of soltd. It was then dissolved m minimum quantity of water, but
soluiio n must be formed. To this solution of 40 gm of ammonium thiocyanate
di ssolved in I SO ml of distilled water was added It was hoiled it

011

gentle

bunscn fl ame untill the boiling solution became turbid due to the separatio n
of phenylthiourea This hot solution was poured in ice cold water. suddenly
,~hu e solid was obtained yield 48 gm, m.p. 154(

Experime nt No. 7 :
Synthesis of l,3-diformamidinothiocarbamide, hydrochlo ride (6a) :
Interaction of tluourea with cyanoguamdrne has been carri ed
out

(i)

111

two different reactio n conditions.

1)

In presence of aqueous hydrochlo1 ic acid, in acetone medium

ii )

In presence of hydrogen chloride m acetone-ether med tum (I: I )

A mixture of cyanoguanidrnc (0 I M), th1ourea (0 I M), HC I ( IO ml).

di stilled water ( 10 ml) and acetone (SO ml) was refluxed on bo1lmg water
bath for 8 hrs Dunng boiling suspended cyanogua11idme went 111to the solution
and a new product was found to be gradually separated o ut. It was filtered in
hot cond ition and crystall ized with aqueous ethanol to get pure (6a), yield
67 7%. m p 26S-66C(d).
(ii)

A mixture of cyanoguanidinc (0. I M), thiourea (0 I M), a cetone (50

ml) and ether (SO ml) was taken. To thi s reaction mixture, di) hydrogen
chloride gas was bubbled ( aCI 16 g and 11 2SO, 25 ml) for 20 minutes Tl11 s
reactio n mixture

\\aS

refluxed for 8 hrs Dunng bo1hng cyanoguanichne went

11110 thc solution and new produc t was fow1d to be separated o ut It was filtered

Chapter . I

in hot condition and crystallized with aqueous ethanol to get pure (6a), yield
79 .8%. m.p. 265-66C(d).

(iii)

Same reaction was carried out in benzene medium . In benzene medium

yield is 3 I%.
As investigated in above reactions the identical product with

m.p . 265-66C(d) has been isolated in (i), (ii) and (iii) only yield is changed.

Experiment No. 8 :
Sy n t h esis of N"-p h e n y lfo rm a m idinoformam idi n ot hi ocarbamide,
hydrochloride (6b) :
The reaction mjxture ofcyanoguanidine (0. 1 M), phenylthiourea
(0. 1 M). acetone (50 ml) and ether (50 ml) was taken in round bottom flask .
Dry hydrogen chloride gas was bubbled for 15 minutes, to this reacti on
1111xture. Thi s reaction mixture was refluxed for 14 hrs. on water bath . The
sticky brown product was isolated, which after trituration with petroleum ether
several times gives (6b), y ield 6 1%, m.p. 182C.

Experiment No. 9 :
Sy nthes is of N"-met h y lfor m a m idinoformamid i noth ioca r bamid e,
hydrochlor ide (6c) :
The reaction mixture of cyanoguanidin e (0. 1 M), methylthiourea
(0. I M), acetone (50 ml) and ether (50 ml) was taken in round bottom fl ask.
Dry hydrogen chloride gas was bubbled for 15 minutes, to this reaction
mixture. This reaction mixture was refluxed for 14 hrs. on water bath . The
sticky brown product was isolated, which after tritmation with petroleum ether
several times gives (6c), yield 53%, m.p. 123C.

Ex1>criment No. 10:

Sy nth es i s of

"-eth y lfo rm a midi n ofo rmam id i no th ioca rba mid e,

hydrochloride (6d) :
T he reaction mixture of cyanoguanid111e (0 I M). ethylth10urea
(0 I M), acetone (50 ml) and ether (50 ml) was taken in round bottom fla sk.
Dry hydrogen chlonde gas was bubbled for 15 111inu1es, to 1h1s reacuon
mixture. T hi s reaction mixture was refluxed for 14 hrs. on water bath. The
sticky brown product was isolated, which after trituration with petroleum ether
several times gives (6d), yield 62%. m.p. 108C.

Ex1>crimcnt No. 11 :
Synthesis of N"-allylformamidlnoformamidinothiocnrbamide (6e) :
A mixture of cyanoguanidine (0. 1 M), allylthiourca (0. 1 M),
acc1one (50 ml) and e ther (50 ml) was taken. Hydrogen chloride gas was
bubbled for 20 minutes, to this reaction mixture. The reaction mixture was
refluxed for 8 hrs on water bath A
new dark yellowish crystalline product of
(6e) was fou nd to be gradually separated ou1 yield 690'

7 0 , m . p 203c

R C P1npal11, Ph O Thesis

64

References

D. T. Tayade

I.

Omnla/J. Chem., 13(2), 189- 190

{1997).

D T. Tayade

2.

Oriental J. Chem., 13(2). 309-3 10

( 1997)

3.

M. G. Pnranjpc

J. /nd1an Chem Soc , 42, 45 ( 1966).

P K Shrivastava

"Bases related with Lhiourea", Ph.D.

Thesis, B.H U. (1964).

D. T. Tayade

"A conuibution to chemistJy of nitrogen.

nitrogen and sulpher contammg
heteroacychc & heterocyclic compOlmd".
Ph.D Thesis Amravati Um. Amravau

( 1996).
M. E. Shelke

"Synthesis of I ,3-D1formamidinothiocarbamide derivatives and thei1

cyclisation to substituted imino/ammo
1,3,5-thiadiazine hydrochloride and
1,3,5-triazines Ph D. Thesis S G B
Amravah Umversity, Amravati (2005)

7.

D.T. Tayade, M.M. Chincholkar

Acta Ciencia lndica, XXl( I). 37-38.

(1995)
8

D T. Tayade, J.S Waghmarc

J Indian Chem. Soc., 83, 1-3 (2006).

aud S.U Patil.

9.

B. Colthup, L. H. Daly,
and S E. Wiberley

"lntroducuon of Infrared and Raman

Spectroscopy", Academic Press, New
York, p. 279 (1964)

10

R.M Silverstein, G.C. Bassler

and T. C Morill

"Spectroscopic lde11tificanon ofOrgru11c

Compounds", 5th Ed., John Wiley and
Sons, Inc .. Ne" York, p. 123 ( 1991)

Chipllf - I

II

12

Margareta Acaram and

C. H. Maleesov

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