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CHAPTER 11

The Nitro Group

11-1.

NO2 STRETCHINGS
A m o n g the six vibrations involving the NO2 group in nitrocompounds,
the NO2 stretchings are the two most useful group frequencies. The antisymmetric stretching m o d e is quite constant in spectral position, while the
symmetric stretching m o d e is more prone to vibrational couphng [1].
Therefore, caution should be exercised in applying the NO2 symmetric
stretching mode as a characteristic vibration. Nevertheless, with the
combination of their spectral positions and intensities, these two characteristic vibrations usually provide enough information for differentiating the
unconjugated [2-6] and conjugated NO2 groupings [3, 4, 7-9]. In addition,
the atom (C, O, or N) adjacent to the NO2 moiety can be determined by the
vibrational spectra of the c o m p o u n d s [10-12]. The C stretching m o d e
is used as a characteristic frequency of NO2 groupings only for smaU
nitroalkanes. However, the vibration is sensitive to the type of nitroalkane
(i.e., primary, secondary, etc.) and to nitroalkanes' rotational conformations. T h u s , these vibrations can be useful in conformational studies.

11-1.1.

Nitroalkanes (R-NO2)

The antisymmetric NO2 stretching m o d e of nitroalkanes was found by


Nyquist [3] to exhibit higher frequencies in the vapor phase (1621-1555 cm"^)
179

180

Chapter 11 :

The Nitro Group

than in the hquid state (1601-1531 cm"^). Usually, the Vas(N02) frequency
decreases by 18-32 cm"^ as the sample phase changes from vapor to hquid
state. O n the other h a n d , the frequency shift of the symmetric NO2
stretching m o d e u p o n a change in the sample state is not as predictable
as that for the corresponding antisymmetric m o d e . The Vs(N02) frequencies
of nitroalkanes can either decrease by as much as 1 0 c m " \ or increase
by as much as 22 c m " S when the measuring state changes from vapor
(1397-1310cm"^) to liquid phase (1381-1310cm"^) [3]. In the IR spectra
of unconjugated nitroalkanes, the intensity of the antisymmetric NO2
stretching band is very strong, while the symmetric stretching b a n d is
somewhat weaker (strong-medium) [4, 13]. The peak intensity ratio of
Vas(N02)/Vs(N02) has been observed to vary from 5.9 to 1.8 in vapor-phase
IR spectra [3]. Although there was no definite number reported for the
intensity ratio in liquid-state IR spectra, the existence of an unconjugated
NO2 group can stiU be recognized by the spectral pattern of these two bands
[4, 13]. The symmetric (2) m o d e is predicted and found to be very
strong and polarized in R a m a n spectra, while the antisymmetric stretching
m o d e exhibits only medium to weak intensity [13]. Therefore, the relative
intensities of the NO2 antisymmetric and symmetric stretchings are reversed
in R a m a n spectra.
Slovetskn et al. Have studied the correlation between the NO2 stretching frequencies and the type of nitroalkanes (i.e., primary, secondary, or
tertiary) by R a m a n spectroscopy [2]. Their results are summarized in Table
11-1 along with correlations from other references. It appears that the
branching on the -carbon a t o m lowers the vibrational frequencies in b o t h
antisymmetric and symmetric NO2 stretching vibrations. Investigations on
the available IR data suggest that these correlations are also appropriate in
interpreting the IR absorption frequencies. The table shows the c o m p o u n d s
used for this examination.

-,^-,

Vas(NO)2

,(2)

1562-1553 cm"^

Ref.

1387-1378 cm"^

4, 14

Me2CH-N02:

1552 cm'^

-1360 cm"^

4, 14, 15

Me3C-N02:

-1540 cm-^

1358 cm-^

to A-C6H13-NO2:

When a CH3 moiety appears on the -carbon a t o m , the interaction


of CH3 symmetric deformation (near 1380 cm"^) with symmetric NO2
stretch wih resuU in two strong IR bands near 1390 c m " ^ and 1360 c m " ^

M.

IM.

181

NO2 Stretchings
Table 1 1 - 1 .
The Group Frequencies (cm"') of NOj Containing Compounds

Vibrational Mode

Compound

Vapor

IR

Liquid/SoHd

IR

1621-1555

vs

1601-1531

vs

m-w

-CH2-NO2

1560-1548

vs

m-w

-CHR-NO2

1553-1547

vs

m-w

-CR2-NO2

1554-1534

vs

m-w

-C(N02)2

1587-1563

vs

m-w

-C(N02)3

1603-1597

vs

1555-1487

vs

1640-1620

vs

1630-1550

vs

NO2 antisymmetric stretch RNO2

-2
O-NO2

1580-1530

vs

N-NO2
NO2 symmetric stretch

1310-1381

vs

-CH2-NO2

1388-1376

vs

-CHR-NO2

1374-1366

vs

-CR2-NO2

1354-1344

vs

-C(N02)2

1337-1327
1357-1318

vs

vs

1285-1270

vs

1300-1250

vs

gauche:

894-873

m-w

trans:

914-898

gauche:

863-847

trans:

908-868

R-NO2

1397-1310

1307-1297

-C(N02)3
-02
0-N02

1371-1325

N-N02
C - N stretch

R-N02
R-CH2-N02
R-CHR-N02

NO2 scissors

NO2 rock

" 3-Nitropentane: 613 cm

m-s
m-w

s
m

R-N02
R-CH2-N02

618-609

R-CHR-N02

627-619^^

857-830

m-w

R-CH2-NO2

643-614

w, sh

R-CHR-NO2

670-650

w-vw

Ar-N02
NO2 wag

m-s

m-w

R-NO2

R-NO2
R-CH2-NO2

494-472

m-w

R-CHR-NO2

557-522

Chapter 11 : The Nitro Group

182

11 - 1 . 2 .

Substituted Nitroalkanes

Table 11-2 iUustrates the influences of substituents on NO2 stretching


frequencies. In this table, the NO2 stretching frequencies of hquid
nitromethane (CH3NO2) are used as standards for comparison. The
frequency shift from NO2 stretchings of CH3NO2 are summarized in the
second and third columns for substituted nitroalkanes. The substitution of
halogen atoms (i.e., F , CI, Br), C = 0 , and NO2 groups on the a-carbon
atom results in a high frequency shift of the antisymmetric NO2 stretching
mode, while the symmetric NO2 stretching frequencies are lowered by
8-29 c m " \ Therefore, the NO2 antisymmetric and symmetric stretchings
bands are farther apart than those of unsubstituted nitroalkanes. O n the
other hand, the NO2 stretching frequencies of most yff-substituted nitroalkanes are only shghtly affected. The exception is )-nitro substitution,
which lowers the symmetric NO2 stretching by 1 5 c m " ^ Nyquist pointed
out that the frequency shift of substituted nitroalkanes is somewhat additive
for antisymmetric and symmetric NO2 stretchings in both vapor and hquid
phases. As an example given in Table 11-2, the antisymmetric NO2
stretchings frequency of CH3CCI2NO2 is estimated to be at 1587 c m " ^
which is only 6 c m " ^ higher than the experimental value of 1581 c m " \
Similarly, the symmetric NO2 stretching frequency of this c o m p o u n d is
calculated to be 1321 c m " ^ and the experimental value was found to be
1325 cm"^ (see Table 11-2).

11-1.3.

Conjugation with a C = C Group

Conjugation with a C = C moiety lowers antisymmetric and symmetric NO2


stretchings most probably through the resonance effect. For nitroethylene,
the two vibrational modes were found at 1566 c m " ^ and 1359 c m " ^ by IR
and R a m a n methods [16]. Brown [7] found that monoalkyl nitroethylenes
absorb infrared radiation strongly in the regions from 1528 to 1520 c m " ^
and from 1359 to 1347 c m " ^ because of the antisymmetric and symmetric
NO2 stretching vibrations. H e also reported that characteristic vibrational
frequencies for di- and trialkyl nitroethylenes are in the regions of 15191511 cm"^ and 1355-1337 c m " \ respectively.
The two strong IR bands at 1514 and 1344 cm"^ for /?-nitrostyrene
(C6H5CH=CHN02) [4] can be attributed to the antisymmetric and symmetric NO2 stretching modes. Our investigation [13a] on four ring-substituted yff-nitrostyrenes indicates that the antisymmetric NO2 stretchings of
these compounds are located near 1530 c m " \ and the symmetric NO2
stretching falls in the region of 1352-1333 cm"^ [13a]. These vibrational

M.

NO2 Stretchings

183
Table

11-2.

Vas(N02) and ,(2) Frequency Shifts of Substituted

Nitrocompounds from Those of CH3NO2

^3(2): 1558 cm-^


,(2): 1375 cm"^

CH3NO2 (Uq., IR)

,3(2)
-substituent:
-H

0
-5
-5

-CH3
-C2H5
-C6H3
- c = o

-F
-Cl
-Br

-NO2
yff-substituent:
-H
-OH
-Cl
-Br

-NO2

,(2)

+ 10
+ 17
+ 17
+ 17
+ 29

0
-8
-8
-8
-8
-23
-23
-23
-29

0
-4
+2
+2
+2

0
-6
-4
-4
-15

Example: CH3CCI2--2
Vas(N02)

1558
+ 1 x(-5)
+ 2 x (17)
calc. 1587 cm" ^
obs. 1581 cm"^

Vs(N02)

1375
+ 1 X ( - 8 ) ...
+ 2 x ( - 2 3 ) ...

1 (-CH3)

2 (-Cl)

calc. 1321 cm~^


obs. 1325 cm"^

frquencies for y-nitrostyrenes are essentially in the same regions as those for
monoalkyl nitroethylenes. T h e NO2 stretchings of m-bis(2-nitropropenyl)benzene,
Me

occur at approximately 1505 cm"^ and 1330 cm"^ [13b]. These frequencies
are similar to those found for di- and trialkyl nitroethylenes. In the IR
spectra of these ring-substituted y^-styrenes, the symmetric NO2 stretching

184

Chapter 11 :

The Nitro Group

b a n d is observed to be as intense as the antisymmetric m o d e in the IR


spectra. The relative intensities of the antisymmetric and symmetric NO2
stretching bands in the R a m a n spectra, however, are similar to those
observed for nitroalkanes [13a, 13b].
Nitroenamines, (R2N)CH=CH(N02), are found to be a special class of
c o m p o u n d s as far as their vibrational spectra are concerned. U n h k e the
other n i t r o c o m p o u n d s , the Vas(N02) m o d e of nitroenamines exhibits a weak
IR b a n d in the region of 1530-1480 cm~^ and is easily confused with the
aromatic ring or CH2 deformations. Ostercamp and Taylor [17] have
rationalized this anomalously weak Vas(N02) band by the high degree of
electronic polarization with the / N C H = C H N O 2 moiety due to the
resonance effect. There are more irregularities about the vibrational spectra
of nitroenamines that can be attributed to the same resonance effect. These
include a weak C = C stretching b a n d in the 1650-1600 cm"^ region of
R a m a n spectra (IR : vs) and an unusually low NO2 symmetric stretching
frequency (1282-1229 cm"^) with strong IR absorption but weak R a m a n
intensity [17].

11-1.4.

Aromatic Nitrocompounds

There exists a large collection of data on the vibrational spectra for


aromatic nitrocompounds [ 9 , 1 6 , 1 8 - 2 8 , 4 1 , 4 2 ] . The NO2 stretching
frequencies of nitrobenzene occur at 1548 c m " ^ and 1360 c m " ^ for the
antisymmetric and symmetric modes, respectively [16]. However, these
frequencies in other substituted nitrobenzenes are affected by the substituents on the benzene ring through inductive effects, resonance effects, and
hydrogen b o n d formation [12]. In general, the characteristic NO2 stretching
frequencies in the regions of 1587-1555 cm"^ and 1357-1318 cm"^ are
assigned to the antisymmetric and symmetric NO2 stretchings, respectively.
Such frequency lowering, in both of these stretching modes, is attributed to
the conjugation of NO2 with the aromatic ring. As with the R a m a n spectra
of nitroethylenes, the IR intensity of the symmetric NO2 stretching is
enhanced by conjugation, and the antisymmetric and symmetric stretching
bands in the IR spectra are found to be very similar in peak intensity. The
relative R a m a n intensities of nitrobenzenes, on the other h a n d , are very
much similar to those found in the R a m a n spectra of nitroalkanes.
The normal coordinate analysis of some nitrobenzenes suggests that some
vibrations of the benzene ring also participate in the so-called NO2 symmetric stretching m o d e [20,29]. Therefore, the NO2 symmetric stretching
m o d e of aromatic nitrocompounds is m o r e complex t h a n that of nitroalkanes. In the vibrational spectra of m a n y /7-nitroanlines or p-nitrophenols,

11-2.

C - N Stretching

185

two NO2 symmetric stretching bands are observed [30-33]. It is found


that intensities as well as spectral positions of this Vs(N02) doublet are
very dependent o n the solvent polarity. Various theories, including selfassociation [32,33] a n d Fermi resonance [31], have been proposed t o
explain the splitting of the Vs(N02) b a n d in these c o m p o u n d s .
The infrared (2) frequencies of 33 nitropyridines were measured by
Perjessy et aL [34]. They reported the NO2 antisymmetric a n d symmetric
stretching b a n d s at 1543-1485 cm"^ a n d 1370-1336 c m " \ respectively.

11-2.

C - N STRETCHING
11-2.1.

Nitroalkanes

The C N stretching m o d e of small nitroalkanes is very strong a n d polarized


in the hquid-state R a m a n spectra. This vibration occurs at 920 c m " ^ for
nitromethane a n d at 877 cm"^ for nitroethane [13c]. However, other
primary nitroalkanes exist as mixtures of trans a n d gauche conformations
due t o the CC rotation of the CCNO2 moiety; hence, t w o C
stretching bands are observed in the region of 914-895 c m " ^ (trans) a n d
894-868 cm"^ (gauche) [35]. In the case of smaU nitroalkanes, the C
stretching b a n d is intense a n d polarized in the R a m a n spectra, whereas the
infrared absorption of this vibration is of medium t o weak intensity. In the
l-nitropropane spectra the t w o polarized R a m a n bands at 895 c m " ^ a n d
868 cm"^ can be assigned t o the C stretchings of the trans a n d gauche
isomers, respectively. T h e C stretching frequencies of secondary
nitroalkanes appear in the lower regions of 908-868 c m " ^ a n d
863-845 c m " ^ For 2-nitropropane, the C stretching of the trans isomer
occurs near 900 cm"^ ( I R : w , R : m w ) , a n d that of the gauche isomer at
850 cm"^ ( I R : m , R : s ) . As the alkyl substituent on the NO2 moiety
becomes larger, the C stretching m o d e is often overwhelmed by other
skeletal vibrations in the spectral region, a n d its assignment becomes
uncertain.

11-2.2.

Aromatic Nitrocompounds

The C stretching m o d e of aromatic nitrocompounds was originally


correlated with a medium IR b a n d in the region of 875-830 c m " ^ However,
recent vibrational studies based o n n o r m a l coordinate analysis revealed that

186

Chapter 11 :

The Nitro Group

C stretching frequencies of aromatic nitrocompounds occur in the


1177-865 c m " ^ region, because of the coupling between this vibrational
mode and other ring vibrations. This is very similar to what happens with
anihnes. The 875-830 cm"^ band is reassigned to a vibration involving NO2
scissoring, and this is discussed in the next section.

11-3.
NO2 DEFORMATIONS
The NO2 deformation vibrations, which include NO2 scissoring (in-plane),
NO2 wagging (out-of-plane), and NO2 rocking (in-plane), usually occur at
frequencies lower than 900 c m " ^ For the majority of c o m p o u n d s , the
scissoring mode possesses the higher vibrational frequency of the three
deformations, and it is by far the most characteristic deformation m o d e .
The NO2 rocking m o d e , on the other hand, has the lowest frequency for
these three deformations.
According to the vibrational assignments of nitroalkanes [ 1 4 , 6 , 3 6 ] ,
nitroethylene [16] and nitrobenzene [16, 21], the NO2 deformation frequencies of unconjugated nitroalkanes are situated at lower frequencies than the
corresponding vibrations of conjugated deformations. In the example of
nitromethane, the NO2 scissors, wagging, and rocking modes are observed
at 656 cm"^ (liq.; IR : s; R : s, p), 608 cm"^ (liq; IR : m; R : w), and 482 cm"^
(liq.; I R : m ; R : m ) , respectively [14]. Other A2-nitroalkanes exhibit NO2
scissoring bands in the region of 658-610cm"^ [14]. The wagging mode
occurs in a wider range of vibrational frequencies, 560-477 cm"^ [14].
Thus, these frequencies are less useful as characteristic frequencies. The
NO2 deformation frequencies of nitrocyclopropane are assigned by
Holtzclaw et al. [36] as fohows: scissoring (hq.; R : 771 c m " \ w), wagging
(liq.; R : 646 c m " \ vw), and rocking (liq.; R : 491 c m " \ m).
The NO2 deformation occur at higher frequencies when conjugated to
C = C or phenyl groups. For instance, the NO2 scissoring of nitroethylene is
located at 8 9 0 c m " \ the NO2 wagging at 7 1 4 c m " \ and the rocking at
652 c m " ^ The NO2 deformation frequencies of nitrobenzene are located in
regions very close to those of nitroethylene, as its NO2 scissoring is reported
to be at 853 c m " ^ the wagging mode at 704 c m " \ and the rocking vibration
at 532 cm~^ [16]. The scissoring mode of other aromatic nitrocompounds is
located in the region of 890-800 cm"^ (R : s-m; IR : s-w) [21-23]. In the case
of l,3,5-triamino-2,4,6-trinitrobenzene, the NO2 scissoring frequency
(IR : 782 cm"^) is lower than the characteristic region [28].

11-5.

Nitroamines ( > - 2 )

187

11-4.
COVALENT NITRATES ( - O - N O 2 )
Only a limited a m o u n t of work has been reported on covalent nitrates. The
antisymmetric and symmetric NO2 stretching b a n d s of covalent nitrates are
located at 1640-1620 cm"^ a n d 1285-1270 cm~\ respectively [11]. It should
be noted that the antisymmetric NO2 stretching may be confused with some
substituted C = C moiety or aromatic ring stretchings. The symmetric NO2
stretching b a n d of primary nitrates usually appears as a single b a n d , while
the secondary nitrates, including monocyclic nitrates, exhibit a doublet
structure in this spectral region. One exception for this correlation is
secondary bicychc nitrates, which display only a single
band in their
vibrational spectra. It is to be expected that this symmetric stretching m o d e
is strong and polarized in the R a m a n spectra.
The O stretching frequency of covalent nitrates is observed at
870-855 cm"^ [11]. The NO2 in-plane bending is found at 710-695 c m " \
and the out-of-plane bending at 760-755 cm"^ [11].

11-5.
NITROAMINES O N - N O 2 )
The NO2 symmetric stretching of the )>NNO2 moiety occurs in a region
very similar to that for the ONO2 g r o u p . Infrared studies indicate
that the characteristic Vs(N02) of nitroamines is located at 1300-1250 cm~^
with very strong IR absorption [10, 37, 38]. The R a m a n intensity of this
vibrational m o d e is expected to be strong and polarized. The antisymmetric
NO2 stretching is m o r e sensitive t o the environmental structure of the
NNO2 moiety. F o r example, the alkyl-substituted nitroguanidines
absorb infrared in the 1634-1605 cm"^ region due to Vas(N02), while the
arylguanidines absorb at lower frequencies (1587-1575 cm~^) [37,38].
Recently, Cherskaya et al, investigated the vibrational spectra of ,'dinitroalkylenediamines, N 0 2 - N H - ( C H 2 ) - N H - N 0 2 (n = 1-3) [39].
T h e Vas(N02) vibration is assigned t o b a n d s between 1596 c m " ^ and
1547 cm"^ ( I R : v s , R : n o t observed), while the Vs(N02) is found in the
region of 1365-1290 cm"^ (IR : s-m, R : s-w). It is noteworthy that in-phase
and out-of-phase Vas(N02), as weh as Vs(N02), are possible for these
c o m p o u n d s because of the presence of two nitro groups, but in this case,
they are very weakly coupled and smah frequency shifts are expected. Such
mechanical interactions of the two NO2 groups should be taken into

Chapter 11 :

188

The Nitro Group

consideration when examining the IR and R a m a n intensities of stretching


modes and the polarization character of R a m a n b a n d s . In these cases, the
N stretching m o d e (1030-980 cm~^) is found to be very strong a n d
polarized in the R a m a n spectra, but weak in the IR.
These a u t h o r s also reported b a n d s for /^,/^'-dinitroalkenediamine s a h s ,
where the N O b o n d s have decreased double-bond character and the N N
b o n d has increased double-bond character. T h e N O a n d N N b o n d s have
rather similar force constants, so the RNNO2" ion somewhat resembles
the NO3" ion. For R - N N O 2 salts, the b a n d at 1310-1280 cm"^ ( I R : s ,
R : w) was assigned t o out-of-phase NO2 stretch. A b a n d at 1475-1430 cm~^
(IR : s, R : s, p) involves the in-phase stretching of the NO2 b o n d s a n d N N
contraction. Assignments were m a d e on the basis of the IR and R a m a n
intensities as well as the polarization character of the R a m a n b a n d s [40].

REFERENCES
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.

E. M. Popov and V. A. Shlyapochnikov, Opt. & Spectrosc. 15, 174, 1963.


V. I. Slovetskii, V. A. Shylapochnikov, S. A. Shevelev, A. A. Fainzirberg, and
S. S. Novikov, Izv. Acad. Nauk. USSR., Otd. Khim. Nauk 330, 1961.
R. A. Nyquist, "The Interpretation of Vapor-Phase Infrared Spectra, Group Frequency
Data," Sadtler Research Laboratories, 1984, pp. 550-608.
C. J. Pouchert, "The Aldrich Library of FT-IR Spectra," Aldrich Chemical Company,
Inc., 1985.
W. H. Lunn, Spectrochim. Acta 16, 1088, 1960.
R. N. Hazeldine, J. Chem. Soc, 2525, 1953.
J. F. Brown, J. Am. Chem. Soc 77, 6341, 1955.
R. R. Randle and D. H. Whiffen, / . Chem. Soc, 4153, 1952.
M. St. C. Flett, Spectrochim. Acta 18, 1537, 1962.
L . J . Bellamy, "The Infrared Spectra of Complex Molecules," John Wiley & Sons, New
York, 1975, pp. 331-346.
R. A. G. Carington, Spectrochim. Acta 16, 1279, 1960.
K. Nakanishi and P. H. Solomon, "Infrared Absorption Spectroscopy," Holden-Day,
Inc., San Francisco, 1976, pp. 45-46.
"The Sadtler Standard Raman Spectra," Sadtler Research Laboratories, 1976.
(a) 1528R, 1529R, 1537R, 1538R. (b) 1527R. (c) 296R, 297R.
D. C. Smith, C. Y. Pan, and J. R. Nielsen, / . Chem. Phys. 18, 706, 1950.
J. R. Durig, J. A. S. Smith, Y. S. Li, and F. M. Wasacz, J. Mol. Struct. 99, 45, 1983.
G. Varsanyi, S. Holly, and L. Imre, Spectrochim. Acta 23A, 1205, 1967.
D. L. Ostercamp and P. J. Taylor, / . Chem. Soc, Perkin Trans. II, 1021, 1985.
B. J. Lindberg and B. Schroder, Acta. Chem. Scand. 24, 3089, 1970.
O. Exner, S. Kovac, and E. Solcaniva, Collect. Czech. Chem. Commun 31, 2156, 1972.
A. Kuwae and K. Machida, Spectrochim. Acta 35A, 27, 1979.
G. Varsanyi, "Assignments for Vibrational Spectra of Seven Hundred Benzene
Derivatives," John Wiley & Sons, New York, 1975.
S. Pinchas, D. Samuel, and B. L. Silver, Spectrochim. Acta 10, 179, 1964.

References
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.

189

. S. Sundar, Spectrochim. Acta 41A, 905, 1985.


J. H. S. Green, W. Kynaston, and A. S. Lindsey, Spectrochim. Acta 17A, 486, 1961.
N. N. Sundar, Spectrochim. Acta 41A, 1449, 1985.
M. Rangacharyulu and D. Premaswarup, Ind. J. Pura & Appl. Phys. 16, 37, 1978.
A. M. C. Fernandez, A. M. T. Gonzalez, and A. G. Chozas, J. Mol. Struct. 143, 557,
1986.
T. G. Towns, Spectrochim. Acta 39A, 801, 1983.
N. Abasebogovic, L. Colombe, and P. Bleckmann, /. Raman Spectrosc. 6, 92, 1977.
L. M. Epstein, E. S. Shubina, L. D. Ashkinadze, and L. A. Kazitsyna, Spectrochim.
Acta3%Ay 317, 1982.
J. F. Bertran, M. Hernandez, and B. L. Serna, Spectrochim. Acta 38A, 149, 1982.
M. Harrand, / . Raman Spectrosc. 4, 531, 1975.
M. Harrand, /. Raman Spectrosc. 8, 161, 1979.
A. Perjessy, D. Rasala, P. Tomasik, and R. Gawinecki, Collect. Czech. Chem.
Commun. 50, 2443, 1985.
G. Geiseler and H. Kesler, Ber. Bunsenges. Phys. Chem. 68, 571, 1964.
J. R. Holtzclaw, W. C. Harris, and S. F. Bush, /. Raman Spectrosc. 9, 257, 1980.
W. D. Kumler, J. Am. Chem. Soc. 76, 814, 1954.
E. Lieber, D. R. Levering, and L J. Patterson, Anal. Chem. 23, 1594, 1951.
N. O. Cherskaya, V. P. GeoreUk, V. A. Shlyapochnikov, V. P. Ivshin, and T. N.
Ivshina, Bull. Acad. Sei. USSR, Div. Chem. Sei. 35, 1385, 1986.
N. O. Cherskaya, V. A. Shlyapochnikov, V. P. Ivshin, and T. N. Ivshina, Bull. Acad.
Sei. USSR, Div. Chem. Sei. 35, 1388, 1986.
J. H. S. Green and D. J. Harrison, Spectrochim. Acta 26A, 1925, 1970.
J. H. S. Green and H. A. Lauwers, Spectrochim. Acta 27A, 817, 1971.

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