Vibrational Spectroscopic Investigation and Conformational Analysis of Methacrylamidoantipyrine: A Comparative Density Functional Study
Table 2
Experimental and calculated vibrational wavenumbers (cm−1) of MAAP.
Mode
P.E.D (≥5%)
Experimental
B3LYP/6-31G++(d,p)
IR
Raman
NH(100)
3249 s, b
3254 s, b
3588
3426
38.29
16.36
CH(97)
3239
3093
0.43
12.83
CH(100)
3094 w
3235
3090
13.53
17.90
CH(89)
3080 vs
3218
3073
3.23
25.29
CH(89)
3059 m
3207
3062
25.36
40.11
CH(90)
3193
3049
13.87
25.64
CH(93)
3044 w
3183
3040
1.14
12.12
CH(87)
3172
3029
2.42
13.11
CH(95)
3167
3025
8.58
8.38
CH(99)
3005 s
3154
3012
4.74
32.59
CH(94)
3136
2995
14.79
17.50
CH(96)
3132
2991
12.80
14.93
CH(99)
2969 s
2968 m
3111
2971
12.02
17.64
CH(92)
3104
2964
12.55
15.67
CH(91)
2919 s
2934 vs
3051
2914
18.10
52.55
CH(98)
3042
2905
21.81
39.66
CH(96)
2863 m
3028
2892
50.02
29.76
OC(74)
1673 vs
1683 s
1743
1703
152.72
26.56
OC(74)
1648 vs
1631 vs
1734
1694
363.40
52.85
CC(69)-5
1702
1663
40.11
111.41
CC(76)
1620 vs
1691
1652
100.80
34.41
CC(65) + HCC(19)
1592 vs
1605 vs
1647
1609
53.05
79.10
CC(69) + HCC(10)
1570 m
1633
1595
2.13
4.99
HNC(58) + CN(10)
1491 vs
1556
1520
352.19
41.25
HCC(60) + CC(10)
1531
1496
105.42
13.21
HCH(85)
1515
1481
15.71
6.95
HCH(84)
1500
1465
2.85
7.29
HCC(81)
1455 vs
1466 m, sh
1499
1465
68.70
2.59
HCC(60) + CC(23)
1491
1457
7.98
1.88
HCH(78)
1484
1450
4.60
13.15
HCH(87)
1477
1443
12.74
7.51
HCH(77)
1446 w
1477
1443
4.71
5.30
HCH(80)
1456
1423
8.18
7.40
HCH(75)
1426 s
1454
1421
7.77
21.77
HCH(67) + CC(11)
1433
1400
76.53
29.21
HCH(77)
1414
1382
5.79
5.84
CC(30) + HCH(19)
1407 s
1392
1360
178.18
19.77
NC(59)
1368 s
1368 vs
1371
1339
88.20
122.68
δHCC(63) + νCC(22)
1360
1329
1.59
2.24
CC(52) + HCC(21)
1310 vs, sh
1303 s
1340
1309
78.89
32.98
CC(42) + HCC(18)
1325
1295
7.14
10.34
NC(39)
1295 vs
1245 w, sh
1292
1263
218.19
34.06
1285 vs
NN(36) + NC(11)
1200 s
1233
1205
85.54
0.69
NN(61) + NC(12)
1211 m
1219
1191
43.20
36.30
HCC(71) + CC(20)
1170 m
1200
1173
1.88
4.90
HCC(78)
1184
1157
0.60
4.78
NC(41) + HCN(16) + HCC(10)
1126 w
1164
1138
5.43
2.93
HCN(55)
1136 s
1156
1130
16.14
8.01
HCN(55) + NC(10)
1105 m
1130
1104
14.51
7.56
CC(38) + HCC(28)
1074 w
1069 w
1104
1079
12.00
0.64
NC(35) + HCC(18)
1060 m
1082
1058
13.07
0.41
HCC(83)
1071
1047
0.12
2.18
HCC(26) + NC(13)
1060
1035
4.98
1.92
δHCC(59)
1057
1032
0.42
0.55
CC(45) + CCC(17)
1026 m
1008 vs
1041
1017
18.61
24.00
δHCC(80)
1001 w
1026
1002
6.02
2.76
CCC(62) + CC(21)
973 w
1014
990
0.17
68.48
HCC(95)
998
975
0.06
0.48
HCC(95)
980
958
0.21
0.17
HCC(32) + CC(22) + NC(11)
956 vw, sh
970
948
13.72
0.75
CC(87)
932 s
946 m
954
932
38.98
3.92
NC(28) + HCC(25)
943
921
6.80
9.61
HCC(79)
922
901
3.20
3.83
CC(28) + HCC(27)
892 w
902 m
907
886
1.89
20.36
HCCN(95)
842 m
858 m
848
829
0.20
3.18
HNCC(43)
806 w
838
819
6.14
4.33
HCCC(53) + CCCC(16)
783 w
803
785
11.75
2.48
HCCC(73)
763 vs
749 w
772
754
42.94
1.70
OCNC(81)
744 m
746
729
13.41
4.16
CC(35) + CNN(20) + HCCC(10)
708 s
705 vw
728
711
42.51
1.35
703 s
HCCC(84)
701
685
16.44
0.60
HCC(25) + CCCC(11)
685 s
678
662
2.43
13.74
HCC(28) + CNN(11)
666 m
656 m
668
653
6.92
5.11
CCC(60)
641 m
658
643
23.86
5.80
CCC(79)
630
616
1.15
7.40
HNCC(57)
603 s
1340
608
56.00
27.67
CCNN(21)
1325
590
11.65
5.02
CCN(30) + CCNN(20) + CC(10)
587 s
1292
575
25.19
15.04
CCO(27) + HNCC(12) + CCNN(10)
622
564
5.98
4.06
NCCC(76)
501 s
604
501
8.72
1.59
CCC(49)
476 w
588
478
8.40
2.76
CCCN(31)
436 m
577
447
19.92
15.42
CNC(26) + CCNC(23)
423 m
512
417
1.68
4.29
CCCC(94)
409 w
397 vw
489
409
0.58
1.88
CCN(49)
373 s
458
383
2.79
7.76
CCCC(32)
427
346
0.60
11.02
CNN(57)
331 m
335 w
419
336
9.39
1.00
CCC(65)
392
305
1.22
3.69
CCN(49)
289 s
295 w
354
284
12.51
4.15
CCC(35)
261 w
275 w
344
271
1.06
1.95
CCCN(41)
312
244
1.68
3.36
CCN(38) + NC(11)
225 vw
290
217
5.16
9.01
HCCC(79)
277
213
0.40
2.36
CCN(37)
200 m
250
207
3.45
21.32
HCCC(90)
169 vw
222
169
0.51
3.26
CCCC(58)
218
157
1.07
5.37
CCNC(47)
140 s
212
141
3.32
7.37
HCCC(54) + CCNC(11)
134 s
173
134
0.62
23.80
CCNC(27) + HCCC(14) + HCC(13)
111 m
160
113
4.87
17.07
CNCC(58)
144
77
1.35
138.91
CNCC(27) + CCNC(17) + CCN(10)
71 vw
137
68
5.61
39.27
CCNN(80)
60 vw
115
55
1.93
72.49
CNCC(56)
50 vw
79
46
2.34
115.46
CNCC(67)
41 vw
70
39
4.55
83.80
CCNC(49) + CNC(16)
57
24
1.74
72.73
: unscaled wavenumbers, : scaled with 0.955 above 1800 cm−1 and 0.977 under 1800 cm−1. IR and R: calculated infrared and Raman intensities. PED data are taken from VEDA4. v: very, s: strong, m: medium, w: weak, b: broad, and sh: shoulder. , , , and denote stretching, bending, torsion, and out modes, respectively.
