CHAPTER 7

Acetylenes

7-1.
INTRODUCTION
A large a m o u n t of literature appeared on the vibrational spectra of
acetylenes during the 1960s and the early 1970s. The vibrational spectra of
alkyl acetylenes were reviewed previously by Sheppard and Simpson [1].
More recently, a few acetylene vapor phase IR spectra were investigated by
Nyquist [43]. More details on the characteristic IR and R a m a n frequencies
were reported by Bellamy [2] and Dolhsh et al. [3], respectively. The
characteristic frequencies of acetylenes arise from vibrations involving
= C H stretching and bending, C = C stretching, and = C C stretching
and bending modes. The values of these vibrational frequencies are
summarized in Table 7-1. More specific values for various compounds are
hsted in Tables 7-2 to 7-4.
The presence of monosubstituted acetylenes can be readily determined by
the strong IR bands due to the = C H stretching and bending modes.
Variable IR intensity is found for the C = C stretching mode of m o n o substituted alkynes. However, this C = C stretching vibration becomes
IR-forbidden when the C ^ C moiety is symmetrically disubstituted.
Fortunately, R a m a n spectrometry provides an easy answer to this problem,
since the C = C stretching is very strong and polarized in the R a m a n spectra.
The spectral position and pattern of R a m a n bands usually provides enough
information to identify the type of substitution.
95

96

Chapter 7:

Acetylenes

Table 7-1.
Characteristic Frequencies o f Acetylenes
Approximate Description
of the Vibration

3340-3290 ( s o i n . )

^ C - H str.

IR

w, p

3320
3320-3310
3303-3281

R - C ^ C - H
GCH2-C=C-H''
M - C = C - H *
^ C - H

F r e q u e n c y ( c m ^)

681-610 ( s o i n . )
640-625
707-675, 663-577

bend.

R - C = C - H
M - C = C - H
C = C str. m o n o s u b s t i t u t e d
R - C = C - H
M - C = C - H *
disubstituted

2130-2100
2130-2120
2055-2019
2250-2200
2325-2290

m-w, dp

var

vs, p

vs, p

s-m

vs, p

vs, p

vw

var

vs, p

vs, p

(Fermi resonance)

2237-2230
2200-2170

R - C ^ C - R '

M-C^C-CH3*
- C = C - C = C -

a s y . str.

H - C = C - C = C - X ^
- C = C - C = C -

H - C ^ C - C ^ C - X "
R - C ^ C - C ^ C - R '
= C C str. m o n o s u b s t i t u t e d
disubstituted
C - C = C - C

a n t i s y m . str.

s y m . str.
^ C - C

2245-2175

s y m . str.

2100-2000
2257-2251

vs, p

1000-940
1160-1005
-1160
842-758

m-w

m-w

m-w

bend

C H 3 - ( C H 2 ) - C = C H , = 0-5
CH2XC=CH^
C H O - C = C - H
C O O H - C = C - H

348-336
314-311, 186-311
261, 226
245, 218

' ' G : H , R , S C H 2 P h , S P h , O P h , N R 2 , F , C I , B r , I.
" X : F , C I , B r , I.

* M : p . A s , S b , Si, G e , Sn.

7-2.
THE C - H STRETCHING OF C ^ C - H GROUPS
The acetylenic C H stretching vibration is characterized by the sharp IR
absorption band in the 3340-3290 cm"^ region (Table 7-2) when measured
in C C I 4 solution. T h e IR intensity of this b a n d is so strong that it is very
distinct and observable even in the presence of the strong, b r o a d O H

7-2.

97

The C - H Stretching of C ^ C - H Groups

b a n d in alcohols or acids (3500-2600 c m " ' ) . T h e weaker shoulder t h a t often

appears at the lower-frequency side of the C H IR b a n d can be explained
by the Fermi resonance effect. This vibrational m o d e is Raman-active
(weak, polarized) in some cases.
Table 7-2 provides a hst of the C - H stretching frequencies for a variety
of c o m p o u n d s in the solution state. Generally, the C - H stretching
frequencies are sensitive t o the substituent on the C = C moiety a n d the
Table 7-2.
The = C H Stretching Frequency (cm~^) of Monosubstituted Alkynes
in CCI4 Solution, etc.
Compounds
(a)

H-C^C-CH3

H-C^C-CHjR
(b) H - C ^ C - C H z X , X = F
Cl, Br, I
OH, O C H 3 ,

O-Ph

SCHj-Ph, S - P h
NR2

H-C=C-CF3

Frequency (cm
3320
3320
3322
3315
3320-3312
-3318
3316-3313
3316

Reference
4
4
4, 5
4, 5
4
4
4
6

3355
3340
3325

7
7
7

(d) H - C = C - C H = C H 2
H-C=C-C(CH3)=CH2
H-C=C-CH=CH(CH3)
H-C=C-COOH
H-C=C-C(=0)C1
H-C=C-C(=0)H
H-C=C-Ph

3305
3315
3300
3306
3301
3335 (vap.)
3316

1
16
16
8
9
17
4

(e)

H-C=C-C=C-H
H-C=C-C=C-C1
H-C=C-C=C-Br
H-C^C-C=C-I

3293
3295
3328
3315

10
11
11
11

(f)

SiH3-C=CH
M(C^C-H)3
M = P, As, Sb
M(C^C-H)4
M = Si, Ge, Sn
CH3M(C=C-H)3
M = Si, Ge

3311 (vap.)
3303-3294

15
12

3299-3293

13

3283-3281
(liq.)

14

(c)

H-C=C-F
H-C^C-Cl
H-C^C-Br

98

Chapter 7:

Acetylenes

Table 7-3.
The C = C Stretching Frequency (cm~^) of Monosubstituted Alkynes
HC=C-X

Frequency

Ref.

HC^C-X

Frequency

Ref.

HC=C-CH3

2130

2121

HC=C-C(=0)H
HC^C-QHj

2080 (liq.)
2113

17

HC=C-CH2R
HC=C-CH20H

2120

HC=C-CH=CH2

2099 (liq.)

HC=C-CH20CH3

2119

2099 (liq.)

1
16

HC^C-CH20-Ph
HC=C-CH2S-Ph

2131-2121
2122

4
4

HC=C-C(CH3)=CH2
HC=C-CH=CH(CH3)
SiH3-C^CH

2054 (vap.)
2052

HC=C-SCH2-Ph
HC=C-CH2NR2

2120
-2100

4
4

P(C=CH)3
As(C=CH)3

2101 (liq.)

16
15
12

2045

12

2025

12

HC=C-CH2F
HC=C-CH2C1

2148

4, 5

Sb(C=CH)3

2131

2055

13

2126

4, 5
4, 5

Si(C^CH)4

HC=C-CH2Br

Ge(C^CH)4

13

HC^C-CH2l
HC=C-CF3

2128

Sn(C=CH)4

2055
2037

13

2255

CH3Si(C=CH)3

2047

14

CH=C-C(CH3)3

2105 (liq.)

19

CH3Ge(C=CH)3

2046

14

HC^C-CRjOH
HC^C-CR20R
HC=C-F

2115-2102
2111-2103

4
4

CH3Sn(C=CH)3

2019

14

2255
2110

7
7

2175, 2005
2244, 2075

10

2238, 2100
2202, 2042

11

HC^C-COOH

2085
2120

HC=C-C(=0)C1

2130

HC^C-Cl
HC=C-Br

8
9

HC^C-C=C-H
HC=C-C^C-C1
HC=C-C^C-Br
HC=C-C=C-I

11
11

physical state of the molecule. As observed for O H vibrations, the

= CH stretching a n d bending modes are affected by weak hydrogen b o n d
formation in the condensed phase. Consequently, it is not surprising that
the gas-phase data (3370-3300cm"^) m a y shift 10-30cm~^ upwards when
compared to those frequencies in the hquid phase. Nyquist [46] reports
3340-3325 cm"^ for 1-alkynes in the vapor state. W h e n a saturated carbon
atom is adjacent to the H C = C moiety, the group frequency is in the
3320-3310 cm~^ region in solution.
Monoalkyl acetylenes absorb near 3320 c m " \ This stretching frequency
is reduced when a heteroatom is attached t o the -carbon a t o m (Table
7-2b). In addition, conjugation with C = 0 or C = C lowers the vibrational
frequency to the 3316-3300 cm~^ region (Table 7-2d). The opposite shift is
observed when a halogen a t o m is connected directly to the triple-bond
carbon (Table 7-2c). A n unusually large spectral shift to below 3300 cm"^
may result if the triple b o n d carbon is attached t o an a t o m with vacant
?-orbitals, such as P , A s , Si, or Ge (Table 7-2f).

7-3.

99

The C - H Bendings of C = C - H Groups

Table 7-4.
The C = C Stretching Frequencies (cm"') of Disubstituted Acetylenes

X-C=C-Y

Frequency

Ref.

CH3-C=C-CH3

2233 (liq.)

19, 20

CHj-C^C-R,

2239-2233

1, 21

R: -alkyl

(liq.)

Frequency

Ref.

C1-C^C-CH2C1

2261

33

c i - c = c - c i

2234

34

Cl-C=C-Br

2205

34

X-C=C-Y

CH3-C=C-CH2C1

2242

22

c i - c ^ c - i

2177

34

CH3-C=C-CH2Br

2242

22

C1-C=C-CF3

2264

35

CH3-C=C-CF3

2271

23

C1-C=C-CN

2195

36

CH3-C=C-C1

2235

24, 25

Br-C=C-CH2Br

2226

33

CH3-C^C-Br

2239

26

Br-C=C-Br

2185

34

CH3-C=C-I

2210

26

Br-C=C-I

2154

37

CH3-C=C-(C=0)C1

2235

Br-C=C-CF3

2235

35

CH3-C=C-CHO

2211

27

Br-C^C-CN

2121

36

R-C=C-R'

2235-2231

21,28,29

I-C^C-I

2118

34

R-C=C-CH20H

2228-2226

21

I-C=C-CF4

2208

35

2250

21

I-C^C-CN

2128

36

R-C^C-C(CH3)20H

2239-2237

21

CF3-C^C-CF3

2305

R-C=C-Br

2219-2201

19, 29

2119

38

R-C=C-I

R-C=C-CH(CH3)OH

CN-C^C-CN

2212-2190

19, 29

P(C-C-CH3)3

2199

39

R-C^C-CH=CH2

2236

16

As(C-C-CH3)3

2189

39

R-C=C-C(=0)CH3

2212-2205

Sb(C=C-CH3)3

2168

39

R-C-C-C^H^

2221-2202

21, 29,

Si(C=C-CH3)4

2197

39

31, 32

Ge(C-C-CH3)4

2192

39

2176

39

Ph-C=C-Ph

2222

40

Pb(C=C-CH3)4

CHO-C=C-Cl

2217

30

CH3-C^C-C=C-CH3

2264 (R)

42

CHO-C^C-Br

2180

30

R-C=C-C=C-R'

2257-2251 (R)

42

CHO-C=C-I

2159

30

2210-2205 (R)

41

Ph-C=C-C=C-Ph

2125-2120 (IR)

7-3.
THE C - H BENDINGS OF C ^ C - H GROUPS
The characteristic IR bands in the 681-610 cm"^ region are attributed to the
= C H bending modes. F o r monoalkyl acetylenes, these vibrational modes
occur in a narrower region of 640-628 cm~\ T h e intensity is usually very
strong in IR, while it is medium t o weak in R a m a n . T h e = C H bending
frequency tends t o be increased or decreased when the substituent decreases

Chapter 7:

100

Acetylenes

or increases the total electron density on the = C H carbon [44]:

N=C-C=C-H

N=C=C=-H

(663 cm"^),

F-C=C-H

i=C=C-H

(578 cm"^).

A n interesting p h e n o m e n o n observed for the = C H bending modes is

that the frequencies are higher in the hquid state t h a n in the gas phase. This
is in contrast to the usual observation for stretching modes, but is typical of
group bending modes involving hydrogen bonding. Nyquist [46] reports
639-629 cm"^ for 1-alkynes in the vapor state. A second feature of these
vibrations is that their overtones give rise to a moderately intense IR b a n d .
However, these overtones fall in the very cluttered fingerprint region at 13001200cm"^ for alkyl acetylenes (1257-1247 cm"^ in the vapor state) [46].
The out-of-plane and in-plane bending modes are degenerate for those
molecules with axial symmetry a b o u t the C = C H g r o u p ; therefore, only
the spectral b a n d will be observed. Examples of such c o m p o u n d s are
C H 3 - C = C H ( 6 3 0 c m - \ soin.) [4], F - C = C H ( 5 7 8 c m - \ vap.) [7],
C 1 - C = C H ( 6 0 4 c m - ^ vap.) [7], and B r - C = C H ( 6 1 8 c m - S vap.) [7].
A splitting of the = C H bending frequencies will be observed when the
c o m p o u n d has no axial symmetry about the C = C moiety. Examples for the
splitting of = C H bending modes can be found in the spectra of propargyl
derivatives ( H C = C C H 2 G , where G is any functional group other than
the H atom) and in the spectra of acetylenes with planar substituents (e.g.,
C = C , C = 0 , or phenyl group) attached to the acetylenic carbon. The
attachment
of
phenyl
group
or
carbonyl
group
adjacent
to
the acetylenic carbon causes greater frequency splitting between the two
bending vibrations. Some examples are the = C H bending frequencies of
H C = C - C 6 H 5 [4], H C = C - C ( = 0 ) O H [8], and H C = C - C ( = 0 ) H [17]
at 648 and 611 cm"^ (soin.), 693 and 650 cm"^ (soin.), and 691 and
669 cm"^ (vap.), respectively. The splitting effect of propargyl derivatives
has been correlated by Nyquist and Potts [4] to the electronegativity of the
G g r o u p . Generally, the splitting in the = C H bending frequencies is
proportional to the difference between the elctronegativities of the G group
and the carbon a t o m . As a result of small differences in electronegativity,
the separation is negligible or unresolvable in the cases of H C = C C H 2 R ,
H C ^ C - C H 2 S - , and H C ^ C - C H 2 l (i.e., G = R, S - , and I, respectively). But the splittings increase to (a) 10-15 cm"^ for H C = C - C H 2 B r
and H C = C - C H 2 C 1 , (b) approximately 25 cm"^ for H C = C - C H 2 N R 2 ,
and (c) 35-38 cm"^ for H C = C - C H 2 0 R and H C = C - C H 2 F . The
= C H bendings occur in the 707-675 cm"^ and 663-577 cm"^ regions for
acetylenes containing atoms such as Si, Ge, Sn, P , A s , and Sb attached t o
the triple b o n d [12-14].

7-4.

C ^ C Stretching

101

7-4.
C ^ C STRETCHING
The polarized C = C stretching band is very prominent in R a m a n spectra,
while its IR intensity varies. This vibration is IR-active only in cases of
monosubstituted or antisymmetric disubstituted acetylenes. Even so, the IR
absorption of R C = C H type c o m p o u n d s is weak, and the intensity
decreases progressively when the triple b o n d moves away from the terminal
position. T h u s , this band is barely observed in the IR spectrum of 2,10dodecadiyne ( C H 3 - C = C - ( C H 2 ) 6 - C = C - C H 3 ) . It appears to be
virtually IR-forbidden when the C = C group is located three or more
positions from the end of the chain. Infrared intensity enhancement of the
C = C stretching b a n d by an acetylinic halogen [7] or conjugation to C = C ,
C = 0 [17] and phenyl [18] groups has been reported.
The C = C stretching frequency of acetylene ( H C = C H ) occurs at
1961 cm"^ (liq.) [3]. This frequency is increased on substitution. For
example, the vibrational frequency of H C = C C H 3 (2142 c m " ^ liq.)
[4] is 181 cm"^ higher than that of acetylene ( H C = C H ) , and that of
C H 3 - C = C - C H 3 (2313 c m - \ liq.) [19] is 352 cm"^ higher than that
observed for acetylene. In the IR (in the vapor state) 1-alkynes absorb
weakly at 2162-2137 cm"^ [46]. Most organic monosubstituted acetylenes
show C = C R a m a n bands in the region of 2130-2100 c m " \ and disubstituted acetylenes are indicated by a b a n d in the 2250-2200 cm"^ region.
The substituent effect on C = C stretching of disubstituted acetylenes is
somewhat parallel to that of monosubstituted acetylenes. For example, the
frequency of H C = C - B r (2085 cm"^) [7] is lower than that of H C = C - C 1
(2110 cm"^) [7], and the same trend is observed in disubstituted compounds
containing chlorine and bromine atoms next to the triple b o n d (Table 7-4).
Monoalkyl ( H C = C R ) acetylenes show characteristic R a m a n bands in the
regions of 2130-2120 cm"^ and dialkyl c o m p o u n d s ( R C = C R ' ) in those
of 2325-2290 cm"^ and 2237-2229 c m " ^ The b a n d in the 2325-2290 cm"^
region of dialkyl acetylenes arises from the Fermi resonance involving the
interaction of the = C C stretch overtone and the C = C stretching. This
band is also observed in many disubstituted alkynes. Such doubUng of the
R a m a n band in this region has been very useful in differentiating the type
of substitution. The attachment of oxygen or sulfur atoms to the a-position
has little effect on the frequency when compared with the values of
alkyl acetylenes. However, a-halogenation raises the frequency to 21482126 c m " \ and the connection of an NR2 group to the a-carbon atom
lowers the vibrational frequency to the 2100 cm"^ region. The effect of
the halogen a t o m adjacent to the C = C moiety on the spectral position

102

Chapter 7:

Acetylenes

(Table 7-3) varies according to the CX b o n d strength [2]. For example, a

fluorine a t o m increases the frequency immensely to 2255 c m " ^ while a
chlorine atom returns the frequency back to the normal region. A bromine
a t o m , on the other hand, decreases the frequency to a value of 2085 c m " ^
Again, a large frequency lowering was reported when an a t o m with vacant
(i-orbitals (P, As, Sb, Si, Ge, Sn) is connected to the acetylenic group
[12-14,39]. Conjugation to a phenyl or C = C group causes frequency
lowering, while conjugation to a C = 0 group shifts the spectral band in a
much less predictable m a n n e r .
For compounds containing the C = C C = C grouping, the vibrational motions are more suitably described as antisymmetric and symmetric
C = C C = C stretchings. The compound H C = C C = C H has
C = C stretching bands at 2172 cm"^ (symmetric stretch) and 2005 cm"^
(antisymmetric stretch). The characteristic R a m a n b a n d (symmetric stretch)
of the R C = C C = C R structure is at 2257-2251 cm"^ (strong,
polarized) [42]. The P h C = C C = C P h type c o m p o u n d s give rise to a
characteristic, very strong R a m a n band at 2210-2205 cm"^ and a medium
to weak IR band at 2125-2120cm"^ (antisymmetric stretch) [41]. The
H C = C C = C X type compounds have strong IR bands at
2244-2202 cm"^ and weak IR bands at 2100-2037 c m " ^ On the basis of
intensity, the higher frequency band was assigned to the antisymmetric
C = C stretch [11]. However, the reverse assignment is true for aU other
diacetylenes above. For these unsymmetrically substituted cases, the higher
frequency band is probably mainly C C = C X stretch, and the lower
frequency band is probably mainly H C = C X stretch, as in previous
correlations.

7-5.
THE C - C STRETCHING OF C ^ C - C MOIETIES
The = C C stretching bands (1161-758 cm"^) are weak in IR and not
simple characteristic frequencies in R a m a n . The identification of these
vibrational bands is more difficult because other types of CC stretching
vibrations also occur in the same region and can interact. The spectral shift
from 1000-940 cm"^ (monosubstituted acetylenes) to 1161-1005 cm~^
(disubstituted acetylenes) does provide a valuable characteristic doublet
feature in the C = C stretching region of dialkyl acetylenes, because of the
Fermi resonance effect with the = C C stretch overtone.

References

103

7-6.
^ C - C BENDINGS
Like the = C H deformations, the two = C C bending modes are
degenerate when axial symmetry about the C = C bond is present. In the
case of no axial symmetry about the C = C b o n d , the two = C C bending
modes are no longer degenerate, and the separation between two spectral
frequencies is dependent u p o n the substitution involved. Only a single CC
deformation R a m a n band (348-336 cm"^) is observed for straight-chain
monoalkyl acetylenes ( C H 3 - ( C H 2 ) - C = C H , = 0-5). In methyl alkyl
acetylenes ( C H 3 C = C R ) , a R a m a n band is seen at 380-366 cm~\ along
with a R a m a n band near 1380 cm"^ (CH3 symmetric deformation) [45].
The a-halogenerated acetylenes ( C H 2 X - C = C H ; X = F , CI, Br, I) [4]
possess two deformation frequencies, at 314-311 cm"^ and 186-158 cm~S
as a result of the loss of degeneracy and the high electronegativity of the
halogen. The presence of a carbonyl group next to the C = C b o n d lowers
the bending frequencies, as exemphfied by H C = C C ( = 0 ) H (261 and
226 cm"^) [17] and H C ^ C - C ( = 0 ) O H (245 and 218 cm"^) [8].

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Chapter 7:

Acetylenes

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