ELECTRONIC SUPPLEMENTARY MATERIAL for
Investigation of aromatic hydrocarbons inclusion into cyclodextrins by Raman spectroscopy and thermal analysis
Inga Tijunelytea, Nathalie Duponta, Irena Milosevica, Carole Barbeya Emmanuel Rinnertb Nathalie Lidgi-Guiguia, Erwann Guenina, Marc Lamy de la Chapellea
a. Laboratoire CSPBAT UMR CNRS 7244, UFR Santé Médecine Biologie Humaine, Université. Paris13, 74 rue Marcel Cachin, 93017 Bobigny, France
b. IFREMER, Laboratoire Détection, Capteurs et Mesures, Unité Recherches et Développements Technologiques, CS10070, 29280 Plouzané, France
Corresponding author: marc.lamydelachapelle@univ-paris13.fr
Submitted to Environmental Science and Pollution Research
Table 6 Calculated frequencies and intensities for the most important normal modes of TOL (among 39 normal modes in Cs representation), experimental data for TOL alone and TOL engaged in complexes with and CD
N°
|
Sym.
|
Calcul.
|
R.I.
|
Assigm.
|
TOL
|
R.I.
|
CD:TOL
|
CD: TOL
|
CD: TOL
|
1
|
A’
|
518
|
4,30
|
(CC stretch.)
|
516
|
1,54
|
520
|
519
|
518
|
2
|
A’
|
783
|
4,00
|
(ring breath.)
|
781
|
5,21
|
787
|
779
|
780
|
3
|
A’
|
999
|
4,19
|
|
999
|
5,20
|
997
|
998
|
998
|
4
|
A’
|
1031
|
1,55
|
|
1026
|
1,29
|
1027
|
1026
|
1026
|
5
|
A’
|
1157
|
0,44
|
(CH sciss.)
|
1152
|
0,43
|
-
|
-
|
-
|
6
|
A’
|
1179
|
0,53
|
(CH sciss.)
|
1175
|
0,38
|
-
|
-
|
-
|
7
|
A’
|
1203
|
1,09
|
(CC stretch.)
|
1206
|
1,52
|
-
|
1204
|
1204
|
8
|
A’
|
1594
|
0,38
|
|
1582
|
0,62
|
1580
|
1581
|
1582
|
9
|
A’
|
1616
|
1
|
|
1603
|
1,00
|
1603
|
1603
|
1603
|
10
|
A’
|
2933
|
1,92
|
(CH sym. stretch. CH3)
|
2921
|
3,62
|
-
|
-
|
|
11
|
A’
|
3060
|
2,39
|
(CH sym. stretch. ring)
|
3058
|
5,53
|
3056
|
3051
|
3053
|
out plane of the molecule
in plane of the molecule
Table 7 Calculated frequencies and intensities for the most important normal modes of NAP (among 48 normal modes in D2h representation), experimental data for NAP alone and NAP engaged in complexes with and CD
N°
|
Sym.
|
Calcul.
|
R.I.
|
Assigm.
|
NAP
|
R.I.
|
CD:NAP
|
R.I.
|
CD:NAP
|
R.I.
|
CD:NAP
|
R.I.
|
1
|
B3g Ag
|
509 (2 bands)
|
1,25;2,32
|
|
508
|
0,42
|
509
|
2,07
|
510
|
1,19
|
510
|
1,50
|
2
|
Ag
|
758
|
2,33
|
(CC stretch.)
|
761
|
1,73
|
763
|
2,39
|
758
|
1,65
|
759
|
1,40
|
3
|
B2g
|
771
|
0,10
|
|
781
|
0,17
|
773
|
0,07
|
773
|
0,16
|
769
|
0,32
|
4
|
Ag
|
1025
|
1,00
|
(CC stretch.)
|
1019
|
1,00
|
1025
|
1,00
|
1024
|
1,00
|
1025
|
1,00
|
5
|
Ag
|
1370
|
2,45
|
(CC stretch.)
|
1379
|
0,88
|
1381
|
2,09
|
1376
|
2,83
|
1376
|
2,80
|
6
|
Ag
|
1582
|
0,34
|
|
1575
|
0,52
|
1578
|
0,79
|
1576
|
0,37
|
1577
|
0,29
|
7
|
B3g
|
1637
|
0,08
|
|
1627
|
0,05
|
1630
|
0,16
|
1629
|
0,14
|
1629
|
0,14
|
8
|
|
|
|
(CH Sym. stretch.)
|
-
|
-
|
3044
|
0,17
|
3045
|
0,20
|
3039
|
0,16
|
9
|
Ag
|
3060
|
0,99
|
(CH Sym. stretch.)
|
3050
|
0,72
|
3057
|
0,62
|
3055
|
0,47
|
3055
|
0,55
|
out plane of the molecule
in plane of the molecule
Table 8 Calculated frequencies and intensities for the 72 normal modes of FL, experimental data for FL alone and FL in complex. Vibrational modes which are most impacted (demonstrated important shift or strongly vary in relative intensity) by complex formation are marked in bold
N°
|
Sym.
|
Calcul.
|
R.I. (reg.1101)
|
Assigm.
|
FL
|
R.I. (reg.1101)
|
Complex
|
R.I. (reg.1102)
|
1
|
B1
|
101
|
0.04
|
|
|
|
|
|
2
|
A2
|
119
|
0.28
|
|
|
|
|
|
3
|
B1
|
163
|
0.02
|
(Rings A)
|
|
|
|
|
4
|
B2
|
204
|
0.28
|
|
204
|
0.11
|
202
|
0.09
|
5
|
A2
|
251
|
---
|
(Rings A)
|
261
|
0.31
|
268
|
0.29
|
6
|
B1
|
293
|
0.66
|
|
300
|
0.70
|
296
|
0.32
|
7
|
A1
|
349
|
0.45
|
|
352
|
0.50
|
350
|
0.39
|
8
|
B1
|
428
|
0.03
|
(Ring B)
|
|
|
|
|
9
|
A2
|
429
|
0.15
|
|
428
|
0.26
|
---
|
---
|
10
|
B1
|
458
|
---
|
(Rings A)
|
452
|
0.10
|
437
|
0.05
|
11
|
B2
|
468
|
0.46
|
|
471
|
0.39
|
469
|
0.27
|
12
|
A1
|
484
|
0.16
|
(Rings A)
|
484
|
0.40
|
479
|
0.77
|
13
|
B2
|
559
|
0.02
|
|
|
|
|
|
14
|
A1
|
560
|
0.58
|
(Rings A)
|
560
|
1.41
|
559
|
0.62
|
15
|
A2
|
564
|
0.01
|
|
|
|
|
|
16
|
B2
|
615
|
---
|
|
|
|
|
|
17
|
B1
|
619
|
---
|
A
|
|
|
|
|
18
|
A2
|
638
|
0.01
|
|
|
|
|
|
19
|
A1
|
672
|
0.45
|
(Ring B)
|
669
|
2.73
|
669
|
0.65
|
20
|
A2
|
736
|
0.01
|
(Rings A)
|
734
|
0.11
|
|
|
21
|
B1
|
742
|
0.01
|
(Ring B)
|
|
|
|
|
22
|
B2
|
762
|
0.01
|
|
|
|
|
|
23
|
B1
|
775
|
0.01
|
(Rings A)
|
778
|
0.20
|
|
|
24
|
A2
|
781
|
---
|
|
|
|
|
|
25
|
A1
|
801
|
0.20
|
(Rings A)
|
801
|
0.58
|
802
|
0.24
|
26
|
B1
|
824
|
0.01
|
(Rings A)
|
825
|
0.12
|
824
|
0.02
|
27
|
A2
|
867
|
0.01
|
(Ring B)
|
|
|
|
|
28
|
A1
|
889
|
0.03
|
|
|
|
|
|
29
|
A2
|
897
|
---
|
(Rings A)
|
|
|
|
|
30
|
B1
|
905
|
0.02
|
(Rings A)
|
904
|
0.17
|
|
|
31
|
B1
|
929
|
---
|
(Ring B)
|
|
|
|
|
32
|
A2
|
957
|
---
|
(Rings A)
|
|
|
|
|
33
|
B1
|
966
|
0.01
|
(Rings A)
|
|
|
|
|
34
|
A2
|
967
|
---
|
(Ring B)
|
|
|
|
|
35
|
B2
|
970
|
0.01
|
|
970
|
0.01
|
|
|
36
|
B2
|
1018
|
0.01
|
(Rings A)
|
|
|
|
|
37
|
A1
|
1023
|
0.34
|
(Ring B)
|
1018
|
1.25
|
1016
|
0.35
|
38
|
A1
|
1041
|
0.12
|
(Rings A)
|
1036
|
0.42
|
1033
|
0.10
|
39
|
B2
|
1084
|
---
|
(Ring B)
|
|
|
|
|
40
|
A1
|
1101
|
1.00
|
|
1101
|
1.00
|
1102
|
1.00
|
41
|
B2
|
1139
|
0.07
|
|
1134
|
0.32
|
1135
|
0.11
|
42
|
A1
|
1159
|
0.03
|
(Ring B)
|
1153
|
0.27
|
1155
|
0.05
|
43
|
B2
|
1161
|
0.01
|
|
|
|
|
|
44
|
A1
|
1184
|
0.10
|
(Rings A)
|
1182
|
0.08
|
1182
|
0.03
|
45
|
B2
|
1210
|
0.13
|
|
1215
|
0.12
|
|
|
46
|
B2
|
1229
|
---
|
(Rings A)
|
1236
|
0.10
|
|
|
47
|
A1
|
1267
|
0.79
|
(Rings A)
|
1269
|
0.70
|
1267
|
0.70
|
48
|
B2
|
1291
|
0.02
|
(Ring B)
|
1299
|
0.12
|
|
|
49
|
A1
|
1314
|
0.02
|
|
1309
|
0.14
|
|
|
50
|
B2
|
1369
|
0.06
|
(Rings A)
|
1361
|
0.18
|
|
|
51
|
A1
|
1375
|
0.18
|
|
1372
|
0.40
|
1372
|
0.40
|
52
|
A1
|
1414
|
0.48
|
|
1409
|
1.71
|
1410
|
0.67
|
53
|
A1
|
1425
|
0.31
|
(Rings A)
|
1423
|
1.20
|
1424
|
1.07
|
54
|
B2
|
1443
|
0.02
|
|
1436
|
0.32
|
|
|
55
|
A1
|
1457
|
0.40
|
|
1455
|
0.90
|
1453
|
0.85
|
56
|
B2
|
1477
|
---
|
|
|
|
|
|
57
|
B2
|
1493
|
0.01
|
|
|
|
|
|
58
|
A1
|
1584
|
0.03
|
(Ring B)
|
1587
|
0.21
|
1590
|
0.16
|
59
|
A1
|
1609
|
0.24
|
CC str.+ CCC Scis. + CCH Scis. (Rings A)
|
1601
|
0.67
|
1604
|
0.25
|
60
|
A1
|
1611
|
0.95
|
CC str.+ CCC.+ CCH Scis. (Rings A)
|
1608
|
1.72
|
1610
|
1.14
|
61
|
B2
|
1614
|
0.23
|
CC str. (Ring B)
|
1620
|
0.12
|
1621
|
0.26
|
62
|
B2
|
1626
|
0.01
|
CC str. (Rings A)
|
|
|
|
|
63
|
B2
|
3034
|
0.03
|
CH str.
|
3022
|
0.17
|
3037
|
0.05
|
64
|
B2
|
3034
|
0.02
|
CH str
|
65
|
A1
|
3034
|
---
|
CH str. (Rings A)
|
66
|
A1
|
3040
|
0.02
|
CH str. (Ring B)
|
3034
|
0.09
|
3051
|
0.24
|
67
|
B2
|
3044
|
0.02
|
CH str. (Rings A)
|
3048
|
0.83
|
3059
|
0.05
|
68
|
A1
|
3045
|
0.08
|
CH str. (Rings A)
|
69
|
B2
|
3050
|
0.05
|
CH str. (Ring B)
|
70
|
B2
|
3056
|
0.02
|
CH str. (Rings A)
|
|
|
|
|
71
|
A1
|
3057
|
0.16
|
CH str. (Rings A)
|
3062
|
0.20
|
3068
|
0.04
|
72
|
A1
|
3061
|
0.15
|
CH str. (Ring B)
|
out plane of the molecule
in plane of the molecule
S
|
