International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
DFT Study of Picric Acid and its Derivative by First
Principles
Abhisek Bajpai2, Apoorva Diwedi2 Subodh Pandey1 Anoop pande3 , Vijay Narayan1*
1 Ram Swaroop Memorial Group of Professional colleges Lucknow
2 Govt. Kakateeya P.G.College jagadalpur
3 Govt Dantesawari P.G.College Dantewada
Abstract
In this work we study the theoretical molecular structure and vibrational spectra of a well known compounds
Picric Acid The equilibrium geometry, harmonic vibrational frequencies, infrared intensities, as well Raman
intensities in scattering activities was calculated by the combination of Density Functional B3LYP method
employing 6-311++ G(d, p) and 6-311G(d,p)as the basis set. The similarities and differences between the
vibrational spectra of the two molecules studied have been highlighted. The molecular HOMO, LUMO
composition, their respective energy gaps, MESP contours/surfaces has also been drawn to explain the electronic
activity of Picric Acid. In general, a good agreement between experimental and calculated normal modes of
vibrations has been observed.
Keywords:, DFT, MESP, Vibrational spectra, HOMO,LUMO
Introduction
Picric acid, also called 2, 4, 6-trinitrophenol, pale yellow,
odourless crystalline solid that has been used as a military
explosive, as a yellow dye, and as an antiseptic. As an
explosive, picric acid was formerly of great importance. Picric
acid was used in the Battle of Omdurman,[1] Second Boer
War,[2] the Russo-Japanese War,[3] and World War I.[4]
Germany began filling artillery shells with TNT in 1902.
Toluene was less readily available than phenol, and TNT is
less powerful than picric acid, but improved safety of
munitions manufacturing and storage caused replacement of
picric acid by TNT for most military purposes between the
World Wars.[1]Ammonium picrate, one of the salts of picric
acid, is used in modern armour-piercing shells because it is
insensitive enough to withstand the severe shock of penetration
before detonating. Picric acid has antiseptic and astringent
properties. For medical use it is incorporated in a surface
ISSN: 2231-5381
anesthetic ointment or solution and in burn ointments. Picric
acid is a much stronger acid than phenol; it decomposes
carbonates and may be titrated with bases. In a basic medium,
lead acetate produces a bright yellow precipitate, lead picrate.
In this study we interpret the simulation of IR spectra of the
title compound with the use of standard 6-311G (d, p),63++G(d,p) basis set. To the best of our knowledge quantum
chemical calculations for picric acid have not been reported so
far in the literature.
Computational details
The entire DFT calculations were performed at Pentium IV
(2.99GHz) personal computer using the Gaussian 03W,
program package [5] utilizing gradient geometry optimization
[6]. The vibrational frequencies associated with ground state
optimized geometry have been evaluated with different level of
theories and 6-311G (d, p) and 6-311++G (d,p) as the basis
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International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
set. Vibrational frequencies obtained by quantum chemistry
calculations are typically larger than that of their experimental
counterpart and thus experimental scaling factors are usually
employed to have better agreement with the experimental
vibrational frequencies [7]. The vibrational frequencies for
given molecule were scaled [8] by .9630 which is calculated
with the B3LYP method. Gauss View 3.0 program [9] has
been considered to get visual animation and also for the
inspection of the Normal Modes Description.
Result and Discussions
interaction between the substituent and the benzene ring. The
average bond length of C-C in benzene ring 1.387A0, 1.389 A0
6-311G (d, p) and 6-311++G (d,p) respectively which is
comparable to the C-C bond length of benzene 1.390 A0.
Vibrational mode analysis
The molecules Picric Acid have 19 molecule so52 normal
modes of fundamental vibration. Detailed description of
vibrational modes can be given by means of normal coordinate
analysis and vibrational assignments are achieved by
comparing the band positions of calculated and experimental
FT-IR and FT-Raman spectra shown in Fig.3 and Fig. 4 of
Picric Acid which is taken from the literature [10-11] with the
calculated spectra of picric acid. Some important modes of
vibration have been discussed as follows and are listed in
Table 2&3.
C-H Stretching
Fig-1 Model molecular structure of Picric
Fig-2 Molecular structure of Picric Acid 2-D Plot
The optimized structure parameters of Picric acid calculated
are listed inTable-1 in accordance with the atom numbering
scheme given in Fig.1&2 In case of Picric acid there is no
point group symmetry .Phenol ring lies nearly in a plane with
two nitro group however 15O-10N-16O bent from plane 43.830
and 44.130 calculated 6-311G (d, p) and 6-311++G (d,p)
respectively to minimized antibonding electron repulsion of
oxygen.A strong hydrogen bond appear 11O…..18H having
separation 1.69A0,6-311G (d, p) and 6-311++G (d,p)
respectively . However two relatively weak bond appear in
given compound 12O…17H and 14O…17H respectively
.Since all the carbon atoms in the benzene ring are sp2
hybridized and having equal bond lengths and bond angles
hence, substitution of hydrogen in benzene ring results in a
perturbation of the valence electron distribution of the
molecule followed by changes in the various chemical and
physical properties. The angular changes in benzene ring
geometry have proved to be a sensitive indicator of the
ISSN: 2231-5381
In higher frequency region almost all vibrations belong to C-H
stretching. In the present study the C-H stretching polarized
along 5C-10N obtained at 3122cm-1 and 3134cm-16-311G (d,
p) and 6-311++G (d, p) respectively. A very intense peak in
both Raman and IR spectra is obtained 3129 cm-1 and 3122
cm-1 6-311G (d, p) and 6-311++G (d, p) respectively are due
to C-H stretching mode having polarization vector 5C-10N. In
case of Picric acid nearly same intensity IR, Raman peak
appears due to the C-H stretching in ring. The magnitude of the
shift in the H-X stretching vibrational frequency is known to
represent a measure of the intermolecular interaction .As see
C-H stretching lies some higher region than benzene This can
be possibly due to the presence of meta directing NO2 which
creates deficiency of electron at meta position and hence the
ring carbon extracts electron from the hydrogen atom and it
reduces the bond strength of C-H. The magnitude of the shift
in the
C-C Ring Vibrations
The ring C-C stretching vibration in Picric acid is calculated at
1576 cm-1 1599cm-1 and 1617cm-1,1587 cm-16-311++G
(d,p)and 6-311G (d, p)respectively which are in approximately
good agreement with the experimental data. Some deviation
can be noticed due to the activating NO2 attached the ring. The
theoretically calculated C-CC bending modes and C-C
torsional modes have been found to be consistent with the
recorded spectral values.
O–H vibrations
In vibrational spectra, the strength of hydrogen bond
determines the position of O–H band. Usually, the O–H
stretching appears at high frequency ranging from 3600–3400
cm-1 [12] because of lower reduced mass. In this study, Picric
Acid showed very strong absorption peaks at 3283cm-1and
3250cm-1by 6-311G (d, p) and 6-311++G (d, p) respectively
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International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
which is due to the O–H stretching vibration. The observed
frequency range is different from experimental one and
probably this is due to the low scattering factor for hydrogen
and also the intermolecular interaction occurring in the
molecule which overestimates the stretching modes. The
various bending vibrations of the hydroxyl groups are also
found to be in good agreement with the Observed spectra and
literature [10-11.].
Electronic Properties
Fig-5 3D Plot of MESP of Picric Acid
Fig-3 Band gap between HOMO-LUMO
The frontier orbitals, HOMO and LUMO determine the way
the molecule interacts with other species. The frontier orbital
gap helps to characterize the chemical reactivity and kinetic
stability of the molecule. A molecule which has a larger orbital
gap is more polarized having more reactive part as far as
reaction is concerned [13]. According to the present Picric
Acid calculations, the frontier orbital gap in case of the given
molecule is 10.09 and 11.15 eV6-311G (d, p) and 6-311++G
(d, p) respectively, for Picric Acid . The 3D and 2D plots of
the HOMO, LUMO and electrostatic potential for both the
molecules are shown in Figures-3-5For Picric acid , HOMO
is located over whole molecule However LUMO is shifted
From para NO2 MESP have been shown to correlate well with
experimentally based quantities such a pKa and other donor
and acceptor values [14]. The MESP is an important factor by
which we can confirm the electrostatic potential region
distribution of size and shape of molecules as well as the total
physiology of the molecules. We have plotted electrostatic
potential contour plots of picric acid as shown in Fig.4.In the
2D plot electric line of field are concentric along Oxygen atom
this indicate that oxygen of O-H acts a negative charge canter.
Conclusion
Fig-4 2D Contour Plot of Picric Acid
ISSN: 2231-5381
In the present work for the proper frequency assignments for
Picric Acid from the FTIR and FT-Raman spectra. The
equilibrium geometries and harmonic frequencies of Picric
Acid were determined and analyzed at DFT level of theory
utilizing 6-311G (d, p) and 6-311++G (d, p) respectively as the
basis set. The present work might encourage the need for an
extensive study by the experimentalists interested in the
vibrational spectra and the structure of these compounds.
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International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
Table-1
Optimized bond length (A0) bond angle of Picric Acid at
B3LYP/6-311++G(d, p)and 6-311G(d, p) level
Bond Length
,Bond Angle
R(1,3)
R(1,4)
R(2,5)
R(2,17)
R(3,6)
R(3,7)
R(4,11)
R(4,12)
R(5,8)
R(5,9)
R(6,8)
R(6,10)
R(7,18)
R(8,19)
R(9,13)
R(9,14)
R(10,15)
R(10,16)
R(11,18)
A(2,1,3)
A(2,1,4)
A(3,1,4)
A(1,2,5)
A(1,2,17)
A(5,2,17)
A(1,3,6)
A(1,3,7)
A(6,3,7)
A(1,4,11)
A(1,4,12)
A(11,4,12)
A(2,5,8)
A(2,5,9)
A(8,5,9)
A(3,6,8)
A(3,6,10)
A(8,6,10)
A(3,7,18)
A(5,8,6)
A(5,8,19)
A(6,8,19)
A(5,9,13)
A(5,9,14)
A(13,9,14)
A(6,10,15)
A(6,10,16)
b3lyp/6311g(d,p)
1.4215
1.4647
1.3811
1.0811
1.4143
1.3169
1.2437
1.2131
1.3932
1.477
1.3783
1.4807
0.9864
1.0817
1.2223
1.222
1.2176
1.2225
1.6953
122.2574
117.4418
120.3007
118.7977
120.2212
120.9795
115.869
124.3682
119.7356
117.4845
118.8784
123.6371
121.5275
119.2561
119.2157
122.5912
120.0272
117.3815
107.6094
118.9276
120.5811
120.4912
117.1181
117.295
125.587
117.3396
116.4019
b3lyp/6-311++g(d,p)
1.3904
1.4215
1.4647
1.3811
1.0811
1.4143
1.3169
1.2437
1.2131
1.3932
1.477
1.3783
1.4807
0.9864
1.0817
1.2223
1.222
1.2176
1.2225
1.6953
122.2574
117.4418
120.3007
118.7977
120.2212
120.9795
115.869
124.3682
119.7356
117.4845
118.8784
123.6371
121.5275
119.2561
119.2157
122.5912
120.0272
117.3815
107.6094
118.9276
120.5811
120.4912
117.1181
117.295
125.587
117.3396
Hratchian,J.B. Cross, C. Adamo,Jaramillo, Gomperts, R.E.Stratmann, O.
Yazyev, A.J. Austin, R. Cammi, C.Pomelli,J.W.Ochterski, P.Y. Ayala, K.
Morokuma, G.A. Voth, P.Salvador, J.J. Dannenberg,V.G.Zakrzewski, S.
Dapprich, A.D.Daniels, M.C. Strain, O. Farkas, D.K. Malick,
A.D.Rabuck,K.Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui,
A.G.Baboul, S Clifford, J.Cioslowski, B.B.Stefanov, G. Liu, A.Liashenko,
P. Piskorz, I. Komaromi, R.L. Martin, D.J.Fox,T. Keith, M.A., Al-Laham,
C.Y. Peng, A. Nanayakkara, M.Challacombe, P.M.W. Gill, B.Johnson,
W.Chen, M.W. Wong,C. Gonzalez, J.A. Pople, Gaussian03 D.01,
Gaussian, Inc.:Pittsburgh, PA, (2003).
[6] H. B. Schlegel, J. Comput. Chem., 3, 214 (1982).
[7] F. Jensen, Introduction to Computational Chemistry, Wiley, New York,
(1999), p. 162.
[8] P.L. Fast, J. Corchado, M.L. Sanches, D.G. Truhlar, J. Phys. Chem.A 103
(1999) 3139.
[9] A.Frisch, A.B.Nelson, AJ.Holder, Gauss view, Inc.Pittsburgh PA, (2000).
[12] V. Krishnakumar and R. Ramasamy, Spectrochim. Acta A61 (2005),
673.
[13] I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John
Wiley and Sons, New York,NY, USA, 1976.
[14] J.S. Murray, T. Brinck, M.E. Grice and P.J. Politzer, J. Mol. Struct. 256
(1992), 29–45.
Reference
[1] Brown, G.I. (1998) The Big Bang: a History of Explosives Sutton
Publishing ISBN 0-7509-1878-0 pp.151-163
[2] John Philip Wisser (1901). The second Boer War, 1899-1900. HudsonKimberly. p. 243. Retrieved 2009-07-22.
[3] Dunnite Smashes Strongest Armor, The New York Times, August 18, 1907
[4] Marc Ferro. The Great War. London and New York: Routeladge Classics,
p. 98.
[5] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A.Robb, J.R.
Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N.Kudin, J.C. Burant,
J.M. Millam, S.S. Iyengar, J.Tomasi,V.Barone, B. Mennucci, M. Cossi, G.
Scalmani, N. Rega, G.A.Petersson, H. Nakatsuji,M.Hada, M. Ehara, K.
Toyota, R.Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y.
Honda,RO.Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P.
ISSN: 2231-5381
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International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
Table-2
Vibrational wave numbers obtained for Picric Acid at B3LYP/6-311++G (d, p) in cm−1 from FT-IR spectra in cm−1, IR intensities
(Km mol−1) and assignment
S.N
.
1
2
3
4
5
6
7
8
9
10
11
12
13
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
Calculate
Frequency
3358
3238
3233
1628
1652
1631
1612
1595
1506
1469
1425
1383
1370
1351
1319
1303
1187
1174
1091
975
960
950
931
849
840
809
781
745
744
728
721
706
646
547
533
511
511
446
402
379
346
340
321
310
198
183
150
124
95
59
51
Scaled
Frequency
3250
3134
3129
1576
1599
1578
1560
1543
1458
1423
1374
1339
1326
1307
1276
1260
1148
1137
1056
944
929
920
901
822
813
783
756
721
720
704
697
683
626
530
516
494
494
431
389
367
335
329
311
300
192
177
145
120
92
57
50
IR
Intensity
409.91
27.88
23.56
277.33
300.12
156.23
38.12
33.34
94.34
215.55
34.58
105.07
379.37
206.09
95.99
154.83
19.88
45.51
91.97
1.54
21.61
42.39
73.44
2.46
.93
87.61
15.34
41.04
7.01
29.74
41.53
4.46
8.48
1.71
5.02
0.81
409.91
27.88
6.36
0.10
0.60
2.16
0.77
0.57
0.29
3.05
2.46
6.39
3.18
0.61
0.24
Raman
Intensity
136.34
28.00
38.67
9.80
1.53
16.77
67.74
39.65
1.23
2.72
9.94
156.30
113.23
16.77
16.00
150.10
37.06
16.36
3.64
.93
.89
.53
4.81
16.69
9.75
1.13
1.16
1.41
2.28
0.68
3.14
1.78
0.47
1.22
0.14
2.35
136.34
28.00
.30
2.01
2.85
8.39
.67
1.54
1.97
0.50
0.25
0.30
0.13
1.74
1.80
Modes of Vibration
ν(7O-18H)
ν(2C-17H)
ν(8C-19H)
ν(CCC)R+ β(2C-17)+ β(7O-8H)
β(8C-19H)+ β(7O-18H)+ ν(CCC)R
νa s(16O-10N-15O)+ νas(1O-4N-12O)+ β(8C-19H)
ν(16O-10N-15O)+ ν(14O-9N-13O)+ β(CH)R+ β(CCC)R
β(CH)R+ β(CCC)R+ ν(14O-9N-13O)
β(CH)R+ β(8C-19O)+ ν(4N-12O)
β (7O-18H) +β(CH)R
β (7O-18H) +β(CH)R+ β(CCC)R
β (7O-18H) +β(8C-19H)R+S(15O-10N-14O)
S(13O-9N-14O)+S(15O-10N-16O)
β(CH)R+ β(CCC)R
β(CH)R+ β(CCC)R+ β(2C-17H)+ β(7O-18H)
β(CH)R+ β(7O-18H)
β(CCC)+ β(CH)R+ β(7O-18H)+ ν(10N-6C)
β(7O-18H)+ β(CH)R
β(CH)R
γ(CH)R
γ(CH)R+ γ(CCC)R
γ(2C-5C-8C)+ γ(CH)R
S(16O-10N-15O)+ β(CH)R+ β(7O-18H)
S (NO2) adjR+ Ring Bending
β(CH)R+Ring Breeding
γ(CH)R+ γ(CCC)R
γ(7O-18H)
β(CH)R+S(15O-10N-16O)
γ(7O-18H)R+ γ(CCC)R+ γ(2C-17H)
γ(13O-9N-14O)+ γ(12O-4N-11O) γ(CCC)R+ γ(8C-19H)
γ(NO2)adjR+ γ(2C-17H)+ β(7O-18H)
γ(7O-18H)+ γ(CH)R+ γ(CCC)R
γ(6C-3C-1C)+ β(2C-17H)R
Ring Breeding
γ(CCC)R
γ(2C-5C-8C)+ γ(8C-19H)
γ(R)+ γ(7C-18H)
γ(CH)R+ γ(CCC)R
Ring R bending+ β(7H-18O)
Ring R breeding
Ring Twist
γ(CCC)R
Ring Twist+ γ(NO2)adj R
γ(2C-17H)+ γ(8C-19H)
Rocking(NO2)adjR
γ(CCC)R+ γ(CH)R
γ(4N-11O)+R(16O-10N-15O)
Ring Twist
T(12O-4N-11O)+ γ(7O-18H)
T(13O-9N-14O)+T(15O-10N-16O)
T(13O-9N-14O)+T(15O-10N-16O)
Polarization
vector
Along 8C-19H
Along 5C-10N
Along 5C-10N
Along 3C-7O
Along 6C-10N
Per R
Making 45with R
Along3C-7O
Along1C-4N
Along 6C-10H
Along 2C-17H
Along 1C-4N
Per to 5C-2C
Along 8C-19H
Along6C-10H
In bett.5C-8C
In bett.3C-6C
Along 5C-9N
Along 3C-17O
45 with R
Per R
Along 5C-9N
Along 2C-17H
Along 8C-19H
Along 5C-9N
Per R
Per R
along 1C-2C
Along 3C-7O
Along 3C-7O
Per R
Along 3C-7O
Along 1C-4N
Along 5C-9N
Per R
Along 2C-5C
450with5C-2C
In plane 2N-5C
Along 5C-2N
450withR
Per. Down.R
Along 1C-4N
Per R
Per R
450withR
Per R
Along R
Notes: ν – stretching; νs – symmetric stretching; νas – asymmetric stretching; β – in-plane-bending; γ – out-of-plane bending; ω –
wagging; R – rocking; T– twisting; τ – torsion, s – scissoring.
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International Journal of Engineering Trends and Technology (IJETT) – Volume 6 Number 3- Dec 2013
Table-3
Vibrational wave numbers obtained for Picric Acid at B3LYP/6-31G (d, p) in cm−1, from FT-IR spectra in cm−1, IR intensities (Km
mol−1) and assignment
S.N.
Calculated
Frequency
1
2
3
4
5
6
7
8
9
10
11
12
13
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
3358.67
3238.36
3233.36
1628.47
1652.54
1631.23
1612.70
1595.02
1506.45
1469.69
1420.04
1383.52
1370.85
1351.12
1319.09
1302.56
1187.09
1174.76
1091.96
975.76
960.05
950.56
931.15
849.27
840.51
809.76
781.376
745.185
744.244
728.202
721.019
706.432
646.918
547.789
533.182
511.128
446.274
402.214
379.655
346.888
340.563
321.603
310.346
198.424
183.902
150.34
124.015
95.2842
59.0355
51.8306
49.9625
Scaled
Frequency
ISSN: 2231-5381
IR
Intensity
Raman
Intensity
Modes of Vibration
Polarization vector
409.91
27.88
23.56
277.33
300.12
156.23
38.12
33.34
94.34
215.55
34.58
105.07
379.37
206.09
95.99
154.83
19.88
45.51
91.97
1.54
21.61
42.39
73.44
2.48
.934
87.61
15.3483
41.0484
7.0104
29.7478
41.5390
4.4633
8.4807
1.7100
5.0254
0.8148
1.5863
2.5443
5.5394
. 0.1528
0.7402
1.0671
0.5349
0.2933
3.0529
2.4653
6.3953
3.1875
0.6197
0.2840
0.0489
136.34
28.00
38.67
9.80
1.53
16.77
67.74
39.65
1.23
2.72
9.94
156.30
113.23
16.77
16.00
150.10
37.06
16.36
3.64
.9315
.898
.534
4.81
16.69
9.75
1.13
1.1694
1.4123
2.2800
0.6805
3.1498
1.7802
0.4702
1.2253
0.1433
2.3567
1.5863
3.1633
0.4735
2.7232
2.5705
7.7351
1.3078
1.9708
0.5000
0.2590
0.3005
0.1398
1.7463
1.8033
1.3573
ν(7O-18H)
ν(2C-17H)
ν(8C-19H)
ν(CCC)R+ β(2C-17)+ β(7O-8H)
β(8C-19H)+ β(7O-18H)+ ν(CCC)R
νa s(16O-10N-15O)+ νas(1O-4N-12O)+ β(8C-19H)
ν(16O-10N-15O)+ ν(14O-9N-13O)+ β(CH)R+ β(CCC)R
β(CH)R+ β(CCC)R+ ν(14O-9N-13O)
β(CH)R+ β(8C-19O)+ ν(4N-12O)
β (7O-18H) +β(CH)R+ β(CCC)R
β (7O-18H) +β(CH)R+ β(CCC)R
β (7O-18H) +β(8C-19H)R+S(15O-10N-14O)
S(13O-9N-14O)+S(15O-10N-16O)
β(CH)R+ β(CCC)R
β(CH)R+ β(CCC)R+ β(2C-17H)+ β(7O-18H)
β(CH)R+ β(7O-18H)
β(CCC)+ β(CH)R+ β(7O-18H)+ ν(10N-6C)
β(7O-18H)+ β(CH)R
β(CH)R
γ(CH)R
γ(CH)R+ γ(CCC)R
β(CH)R+ β(CCC)R+S(14O-9N-13O)
S(16O-10N-15O)+ β(CH)R+ β(7O-18H)+ ν(NO2-6C)
S (NO2) adjR+ β(CCC)R
β(CH)R+Ring Breeding
γ(7O-18H)
γ(7O-18H)
β(CH)R+S(15O-10N-16O)
γ(7O-18H)R+ γ(CCC)R+ γ(2C-17H)
γ(13O-9N-14O)+ γ(12O-4N-11O) γ(CCC)R+ γ(8C-19H)
γ(NO2)adjR+ γ(2C-17H)+ β(7O-18H)
γ(7O-18H)+ γ(CH)R+ γ(CCC)R
γ(6C-3C-1C)+ β(2C-17H)R
Ring Breeding
γ(CCC)R
γ(2C-5C-8C)+ γ(8C-19H)
γ(R)+ γ(7C-18H)
γ(CH)R+ γ(CCC)R
Ring R bending+ β(7H-18O)
Ring R breeding
Ring Twist
γ(CCC)R
Ring Twist+ γ(NO2)adj R
γ(2C-17H)+ γ(8C-19H)
Rocking(NO2)adjR
γ(CCC)R+ γ(CH)R
γ(4N-11O)+R(16O-10N-15O)
Ring Twist
T(12O-4N-11O)+ γ(7O-18H)
T(13O-9N-14O)+T(15O-10N-16O)
T(13O-9N-14O)+T(15O-10N-16O)
Along 8C-19H
Along 5C-10N
Along 5C-10N
Along 3C-7O
Along 6C-10N
Per R
Making 45with R
Along3C-7O
Along1C-4N
Along 6C-10H
Along 2C-17H
Along 1C-4N
Per to 5C-2C
Along 8C-19H
Along6C-10H
In bett.5C-8C
In bett.3C-6C
Along 5C-9N
Along 3C-17O
45 with R
Per R
Along 5C-9N
Along 2C-17H
Along 8C-19H
Along 5C-9N
Per R
Per R
along 1C-2C
Along 3C-7O
Along 3C-7O
http://www.ijettjournal.org
Per R
Along 3C-7O
Along 1C-4N
Along 5C-9N
Per R
Along 2C-5C
450with5C-2C
In plane 2N-5C
Along 5C-2N
450withR
Per. Down.R
Along 1C-4N
Per R
Per R
450withR
Per R
Along R
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