Physicochemical Characterization of the Loganic Acid–IR, Raman, UV-Vis and Luminescence Spectra Analyzed in Terms of Quantum Chemical DFT Approach
Abstract
:1. Introduction
2. Results and Discussion
2.1. Molecular Geometry
2.2. Vibrational Spectra
2.2.1. Vibrations of the Cyclopentane[c]pyran System (Φ, φ and Coupled Φφ)
2.2.2. Vibrations of the Pyran Ring
2.2.3. Carboxylic Group Vibrations
2.2.4. Vibrations of the C–O–C, i.e., θ-O-ΦBridged Bond
2.2.5. Vibrations of the CH, CH2, and CH3 Chromophores
2.3. UV-Vis and Luminescence Spectra-Electron States and NBO Analysis
- The polar character of the C–O–C bridge follows from the positive 0.437 and 0.456 values of the charges on the carbon Cθand CΦatoms and the negative value of −0.591 on the oxygen atom.
- Oxygen atoms inside the θring and Φring exhibit the charges −0.61 and −0.59, respectively, i.e., they have similar character.
- All the hydroxyl groups appearing in the loganic molecule exhibit similar electron properties—the atomic charges of the oxygen atoms take the values from −0.735 to −0.755.
- The charges of the carbon atoms differ depending on the place inside the ring and substituent bonded to this atom. The carbon atoms of the pyran θring have positive charge (0.095, 0.107, 0.115, 0.105, and 0.437)—the greatest value corresponds to the atom bonded to the bridging oxygen. Another situation appears in the coupled cyclopentane-pyran Φφsystem. Its carbon atoms change their charge from positive values, 0.456, 0.259, and 0.202, to negative, −0.220, −0.224, −0.245, −0.255, and −0.403. The greatest value appears for the carbon joining the bridging oxygen atom and the smallest value belongs to the C15 atom in the φring.
- The peculiar situation is observed for the carboxyl group where the C25 atom has charge 0.822, the O9 oxygen atom of the C=O group has charge −0.633, the O8 oxygen atom of the OH group has charge ™0.711, and the H49 hydrogen atom has charge 0.483 (see atomic numbering in Figure 1).
3. Materials and Methods
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Bond Distances | Calc. | Exp. | Bond Angles | Calc. | Exp. |
---|---|---|---|---|---|
O1—C16 | 1.442 | 1.426 | C11—O1—C19 | 115.5 | 114.7 |
O2—C16 | 1.475 | 1.432 | O1—C16—O2 | 108.7 | 109.6 |
O2—C20 | 1.374 | 1.357 | C16—O2—C20 | 116.6 | 115.0 |
C20—C17 | 1.354 | 1.333 | O2—C20—C17 | 125.1 | 124.4 |
C17—C12 | 1.502 | 1.510 | C20—C17—C12 | 122.0 | 123.2 |
C12—C11 | 1.561 | 1.549 | C17—C12—C11 | 110.7 | 110.7 |
C11—C16 | 1.515 | 1.509 | C17—C12—C15 | 113.9 | 112.3 |
C12—C15 | 1.551 | 1.551 | C12—C11—C16 | 113.2 | 113.0 |
C15—C14 | 1.139 | 1.522 | C11—C16—O2 | 111.6 | 113.1 |
C14—C13 | 1.562 | 1.522 | O1—C19—O4 | 107.7 | 107.5 |
C13—C11 | 1.566 | 1.535 | C19—O4—C24 | 1132 | 111.7 |
C17—C25 | 1.466 | 1.482 | O4—C24—C23 | 107.5 | 108.8 |
C25—O9 | 1.243 | 1.197 | C24—C23—C22 | 110.0 | 110.7 |
C25—O8 | 1.389 | 1.341 | C23—C22—C21 | 111.3 | 111.1 |
C14—O3 | 1.457 | 1.439 | C22—C21—C19 | 109.1 | 108.4 |
C13—C18 | 1.537 | 1.528 | C12—C15—C14 | 104.8 | 106.3 |
O1—C19 | 1.432 | 1.396 | C15—C14—C13 | 105.8 | 103.9 |
O4—C19 | 1.448 | 1.433 | C12—C11—C13 | 106.8 | 104.4 |
O4—C24 | 1.473 | 1.422 | C16—C11—C13 | 112.6 | 114.2 |
C23—C24 | 1.534 | 1.530 | C20—C17—C25 | 115.5 | 120.0 |
C23—C22 | 1.526 | 1.529 | C17—C25—O9 | 126.7 | 123.5 |
C22—C21 | 1.522 | 1.515 | C17—C25—O8 | 113.0 | 113.4 |
C21—C19 | 1.523 | 1.511 | C15—C14—O3 | 113.1 | 111.9 |
C24—C26 | 1.512 | 1.507 | C14—C13—C18 | 114.1 | 115.5 |
C26—O10 | 1.453 | 1.418 | O4—C24—C26 | 107.8 | 107.0 |
C23—O7 | 1.447 | 1.415 | C24—C23—O7 | 108.2 | 112.1 |
C22—O6 | 1.450 | 1.414 | C23—C22—O6 | 106.6 | 111.1 |
C21—O5 | 1.449 | 1.419 | C22—C21—O5 | 106.3 | 108.7 |
Torsion angles | Calc. | Exp. | |||
C20—C17—C12—C15 | −122.4 | −117.3 | |||
O2—C16—C11—C13 | 68.0 | 67.5 | |||
C16—O1—C19—O4 | −67.2 | −87.5 | |||
C16—O1—C19—C21 | 174.9 | 153.2 | |||
C14—C13—C11—C16 | −138.5 | −165.4 |
No. | Calculated | Experimental | Assignment for Monomer | |||
---|---|---|---|---|---|---|
dimer | monomer | IR | RS | |||
1 | 3582 | 3582 | 3695(12,2) | ν(OH)-θ(99) | ||
2 | 3579 | 3579 | 3684(11,2) | ν(OH)-φ(98) | ||
3 | 3571 | 3571 | 3653(17,1) | ν(OH)-φ(99) | ||
4 | 3570 | 3570 | 3650(6,0) | ν(OH)-θ(98) | ||
5 | 3551 | 3551 | 3642(17,1) | 3400 sh | ν(OH⋅⋅⋅O)-θ(99) | |
6 | 3208 | 3208 | 3613(28,2) | 3334 vs,b | ν(OH⋅⋅⋅O)-Φ(98) (A group) | |
7 | 3098 | 3098 | 3081(0,2) | ν(CH)-Φ(99) | ||
8 | 3091 | 3091 | 2995(7,2) | 3086 sh | 3083 w | ν(CH)-Φ(99) |
9 | 3089 | 3089 | 2993(7,2) | νas(CH3)-Φ(99) | ||
10 | 3061 | 3061 | 2998(3,2) | νas(CH2)-φ(89) | ||
11 | 3026 | 3026 | 2974(10,1) | νas(CH3)-φ(97) | ||
12 | 3025 | 3025 | 2964(5,1) | ν(CH)-Φ(94) | ||
13 | 3014, 3008 | 3014, 3008 | 2946(10,3) | νas(CH2)-θ(93) | ||
14 | 2999 | 2999 | 2936(2,1) | ν(CH)-Φ(92) | ||
15 | 2997 | 2997 | 2934(10,2) | ν(CH)-θ(74) | ||
16 | 2992 | 2992 | 2925(6,2) | νas(CH2)-φ(82) | ||
17 | 2987 | 2987 | 2922(4,3) | ν(CH)-θ(85) | ||
18 | 2980 | 2980 | 2917(7,3) | ν(CH)-φ(75) | ||
19 | 2971 | 2971 | 2889(28,1) | νs(CH3)-φ(93) | ||
20 | 2967 | 2967 | 2885(8,1) | 2963 s | 2963 sh | ν(CH)-θ(98) |
21 | 2958 | 2958 | 2876(2,3) | ν(CH)-θ(90) | ||
22 | 2956 | 2956 | 2868(2,3) | 2928 s | 2936 vs | νs(CH2)-θ(91) |
23 | 2867 | 2833(16,3) | 2882 s | 2884 s | ν(CH)-θ(96) | |
24 | 2726 | 2822(2,0) | νs(CH2)-φ(89) | |||
25 | 1644 | 1638 | 1747(92,2) | 1677 s | 1682 s | ν(C=O)-Φ(A group) (69) |
26 | 1615 | 1605 | 1623(100,8) | 1632 s | 1634 vs | ν(Φ) (45) + ν(C=O) (A group) (17) |
27 | 1519 | 1519 | 1486(2,1) | 1517 vw | 1526 vw | δas(CH2)-θ(75) + δ(COH)-θ(11) |
28 | 1517 | 1517 | 1481(1,1) | δas(CH2)-φ(77) | ||
29 | 1511 | 1511 | 1477(2,1) | 1490 sh | δas(CH3)-φ(87) | |
30 | 1503 | 1503 | 1468(2,1) | 1481 sh | δas(CH3)-φ(90) | |
31 | 1460 | 1442(1,0) | 1458 w | 1459 m | δ(CH2OH)-θ(72) | |
32 | 1449 | 1449 | 1415(2,1) | 1454 sh | δ(COH)-θ(42) + δ(CCH)-θ(31) | |
33 | 1439 | 1404(9,0) | δs(CH3)-φ(56) + δ(CCH)-φ(24) | |||
34 | 1435 | 1434 | 1405(1,0) | δ(COH)-θ(53) + δ(CCH)-θ(34) | ||
35 | 1425 | 1425 | 1404(1,1) | ν(θ) (49) + ν(COC) (25) | ||
36 | 1416 | 1416 | 1396(1,1) | 1416 w | 1416 sh | ν(θ) (43) + ν(COC) (30) |
37 | 1410 | 1410 | 1394(7,0) | 1412 sh | 1408 sh | ν(φ) (59) |
38 | 1403 | 1403 | 1385(1,0) | ν(φ) (49) + δ(COH)-φ(34) | ||
39 | 1403 | 1402 | 1377(6,0) | 1405 sh | ν(θ) (58) + δ(CCH)-θ(24) | |
40 | 1397 | 1397 | 1375(0,1) | ν(Φ) (93) | ||
41 | 1382 | 1382 | 1368(5,1) | 1384 sh | ν(φ) (84) | |
42 | 1376 | 1376 | 1363(9,1) | 1378 sh | ν(φ) (78) | |
43 | 1371 | 1371 | 1349(9,0) | 1374 w | 1372 m | ν(φ) (38) + δ(CCH)-φ(29) |
44 | 1369 | 1369 | 1347(13,0) | 1363 sh | ν(θ) (54) + δ(CCH)-θ(27) | |
45 | 1355 | 1355 | 1341(2,0) | ν(COC) (27) + δ(CCH)-Φ(25) | ||
46 | 1353 | 1353 | 1337(4,1) | ν(COC) (29) + ν(Φ) (25) | ||
47 | 1351 | 1351 | 1329(3,1) | ν(Φ) (72) | ||
48 | 1345 | 1345 | 1325(5,0) | 1347 w | ν(θ) (50) + δ(COH)-θ(25) | |
49 | 1337 | 1337 | 1324(16,0) | 1340 sh | ν(θ) (55) + ν(COC) (32) | |
50 | 1330 | 1330 | 1304(14,0) | 1331 w | ν(φ) (44) + δ(CCH)-φ(23) | |
51 | 1323 | 1323 | 1299(2,0) | ν(θ) (60) + δ(COH)-θ(21) | ||
52 | 1308 | 1308 | 1284(6,0) | 1310 sh | ν(φ) (41) + δ(CCH)-φ(35) | |
53 | 1301 | 1295 | 1267(1,1) | ν(Φ) (47) + δ(CCH)-Φ(22) | ||
54 | 1295 | 1294 | 1264(2,0) | 1295 sh | ν(φ) (35) + δ(CCH)-φ(24) | |
55 | 1293 | 1292 | 1254(11,0) | ν(C-CH3)-θ(54) + δ(COH)-θ((19) | ||
56 | 1283 | 1283 | 1241(5,0) | 1276 m | 1276 sh | δ(CH2)-θ(64) + δ(COH)-θ(34) |
57 | 1261 | 1261 | 1238(12,1) | 1260 sh | 1264 w | δ(COH)-θ(55) |
58 | 1239 | 1239 | 1223(6,0) | 1254 sh | ν(φ)-(49) + δ(CCH)-φ(29) | |
59 | 1238 | 1238 | 1221(8,0) | δ(COH)-φ(44) + δ(CCH)-φ(35) | ||
60 | 1230 | 1230 | 1219(12,1) | δ(CCH)-θ(71) + ν(C–C)-θ(24) | ||
61 | 1222 | 1222 | 1201(15,0) | ν(φ) (35) + δ(CCH)–Φ(34) + ν(Φ) (29) | ||
62 | 1220 | 1239 | 1180(31,0) | ν(θ) (53) + δ(CCH)-θ(27) + δ(COH)-θ(10) | ||
63 | 1196 | 1194 | 1177(33,1) | 1202 sh | 1200 w | ν(φ) (47) + δ(C-COOH)-Φ(38) |
64 | 1191 | 1191 | 1163(22,0) | 1182 m | 1185 sh | δ(C-COOH)-Φ(44) + ν(Φ) (41) |
65 | 1163 | 1162 | 1148(9,1) | ν(Φ) (41) + δ(CCH)-Φ(36) | ||
66 | 1149 | 1148 | 1134(7,2) | 1153 m | 1150 sh | νas(C–O–C) (53) + ν(C-COH)-θ(41) |
67 | 1138 | 1138 | 1130 (4,0) | ν(C-CH3)-φ(76) + ν(C-C)-θ(22) | ||
68 | 1136 | 1136 | 1117(11,0) | ν(θ) (96) | ||
69 | 1121 | 1121 | 1108(10,1) | 1121 sh | 1124 sh | ν(C-CH3)-φ(65) + ν(C-OH)-φ(30) |
70 | 1101 | 1101 | 1097(20,1) | 1117 m | ν(C-OH) θ(51) + ν(θ) (45) | |
71 | 1088 | 1088 | 1091(1,1) | 1099 sh | ν(θ) (55) + δ(COH)-θ(42) | |
72 | 1080 | 1078 | 1083(10,1) | 1083 m | ν(θ) (74) + δ(COH)-θ(22) | |
73 | 1077 | 1075 | 1077(51,3) | ν(θ) (52) + δ(COH)-θ(46) | ||
74 | 1072 | 1069 | 1068(92,0) | 1067 w | δ(COH)-θ(54) + ν(C–C)-θ(42) | |
75 | 1066 | 1064 | 1058(9,1) | 1066 vs | ν(φ) (71) + δ(CCH)-φ(26) | |
76 | 1059 | 1058 | 1049(37,1) | ν(θ) (53) + ν(COH)-θ(43) | ||
77 | 1051 | 1051 | 1046(20,1) | 1047 sh | ν(C-OH)-φ(48) + ν(C-CH3)-φ(41) | |
78 | 1043 | 1042 | 1040(56,0) | ν(φ) (54) + δ(CCH)-φ(44) | ||
79 | 1035 | 1034 | 1039(54,1) | ν(θ) (94) | ||
80 | 1026 | 1026 | 1029(50,0) | 1028 vs | 1029 sh | ν(φ) (46) + ν(Φ) (45) |
81 | 1021 | 1019 | 1018(49,0) | ν(C-OH)-φ(51) + δ(C-CH3)-φ(44) | ||
82 | 1015 | 999(39,0) | 1016 sh | δ(φ) (96) | ||
83 | 1006 | 1006 | 990(28,0) | δ(θ) (96) | ||
84 | 997 | 997 | 979(6,0) | 995 vs | 999 w | δ(Φ) (97) |
85 | 994 | 993 | 978(11,1) | δ(θ) (55) + νs(C–O–C) (43) | ||
86 | 978 | 977 | 977(36,1) | 978 sh | 979 vw | δ(θ) (66) + νs(C–O–C) (32) |
87 | 971 | 971 | 971(11.1) | 967 sh | 968 sh | δ(θ) (52) + ν(C-OH) (41) |
88 | 959 | 958 | 952(2,0) | 937 w | 937 sh | νs(C–O–C) (52) + δ(Φ + φ) (46) |
89 | 917 | 916 | 918(11,0) | 901 sh | γ(C-CH3)-φ(74) + δ(φ) (23) | |
90 | 895 | 894 | 897(3,1) | 894 m | 897 w | δ(θ) (55) + δ(C-CH3)-θ(41) |
91 | 876 | 876 | 886(25,1) | 864 m | 865 w | δ(φ) (94) |
92 | 846 | 846 | 843(4,2) | 835 w | 837 w | γ(Φ) (95) |
93 | 812 | 811 | 826(36,1) | 806 vw | γ(Φ-φ) (88) | |
94 | 789 | 789 | 784(2,3) | 772 w | 796 vw | γ(Φ-COOH) (68) + γ(Φ) (31) |
95 | 757 | 756 | 772(12,1) | 752 w | 759 m | γ(Φ-COOH) (48) + γ(Φ) (46) |
96 | 741 | 729 | 730(1,5) | 726 w | 725 vw | γ(Φ-COOH) (61) + γ(Φ) (33) |
97 | 704 | 701 | 700(2,1) | 704 vw | δ(C–O–C) (49) + τ(Φ-COOH) (43) | |
98 | 682 | 679 | 669(22,2) | 673 w | 678 vw | δ(C–O–C) (78) + ρ(Φ-COOH) (21) |
99 | 650 | 650 | 660(1,0) | 667 sh | τ(Φ-COOH) (86) + γ(φ) (13) | |
100 | 615 | 615 | 614(10,0) | 634 w | 631 vw | τ(θ-CH2OH) (48) + τ(φ-COOH) (43) |
101 | 609 | 609 | 606(11,1) | 623 w | 614 vw | τ(Φ-COOH) (61) + γ(φ) (33) |
102 | 603(5,0) | 601 vw | γ(C–O–C) (51) + τ(Φ-COOH) (38) | |||
103 | 590 | 590 | 598(8,2) | 593 vw | γ(θ) (47) + γ(θ-OH) (44) | |
104 | 583 | 583 | 587(6,1) | 587 sh | γ(φ) (58) + τ(φ-CH3) (43) | |
105 | 564 | 560 | 560 (1,1) | 573 w | γ(θ-O-Φ) (93) | |
106 | 551 | 538 | 540(16,1) | 538 sh | γ(Φ) (89) | |
107 | 532 | 526 | 523(2,2) | 532 w 530 w | 533 m | τ(Φ-COOH) (64) + γ(Φ-C–O–C) (32) |
108 | 517 | 505 | 497(2,1) | 522 sh 505 w | τ(θ-OH) (39) + τ(θ-CH2OH) (37) + γ(θ) (20) | |
109 | 476 | 471 | 472(3,1) | 487 w | 485 w | γ(φ) (56) + τ(θ-OH) (37) |
110 | 465 | 462 | 451(2,2) | 475 vw | τ(θ-OH) (61) + γ(θ) (37) | |
111 | 452 | 448 | 442(1,1) | 455 vw | τ(θ-OH) (54) + γ(θ) (36) | |
112 | 441 | 441 | 428(5,2) | τ(θ-OH) (62) + τ(θ) (31) | ||
113 | 433 | 433 | 417(20,3) | τ(θ) (47) + γ(θ-O-Φ) (43) | ||
114 | 425 | 424 | 409(17,1) | 421 w | τ(φ-OH) (34) + γ(Φ) (32) + τ(θ) (31) | |
115 | 417 | 416 | 389(4,1) | 419 vw | γ(θ) (51) + τ(θ-OH) (43) | |
116 | 400 | 399 | 380(35,4) | τ(φ-OH)(31) + τ(φ-CH3) (30) + τ(θ-CH2OH) (29) | ||
117 | 386 | 382 | 371(1,1) | τ(φ-CH3) (33) + τ(θ-OH) (32) + τ(θ-O-Φ) (32) | ||
118 | 370 | 368 | 337(6,5) | 362 sh | γ(θ) (64) + τ(θ-CH2OH) (32) | |
119 | 336 | 335 | 312(1,2) | 333 w | ω(θ-O-Φφ) (94) | |
120 | 329 | 319 | 307(2,1) | 328 vw | τ(HO-θ-OH) (48) + τ(HO-φ/Φ) (45) | |
121 | 310 | 302 | 291(1,3) | τ(HO-φ-CH3) (94) | ||
122 | 298 | 292 | 287(1,1) | τ(HO-φ-CH3) (68) + ρ(θ-OH) (37) | ||
123 | 287 | 287 | 281(2,1) | ρ(φ-CH3) (38) + ρ(θ-OH) ((29) + ρ(φ-OH) (29) | ||
124 | 284 | 283 | 263(21,0) | τ(φ-OH) (95) | ||
125 | 270 | 268 | 244(3,1) | 266 w | τ(HO-θ-OH) (53) + τ(θ) (41) | |
126 | 263 | 251 | 233(8,2) | τ(θ-CH2OH) (57) + τ(HO-θ-OH) (41) | ||
127 | 244 | 244 | 228(5,2) | τ(φ) (47) + τ(φ-COOH) (45) | ||
128 | 234 | 233 | 224(18,3) | τ(φ-CH3) (96) | ||
129 | 230 | 230 | 217(10,3) | 227 vw | τ(θ-CH2OH) (53) + τ(HO-θ-OH) (46) | |
130 | 221 | 218 | 202(7,3) | τ(φ-COOH) (66) + τ(φ) (31) | ||
131 | 215 | 214 | 191(0,2) | 204 sh | τ(θ-CH2OH) (93) | |
132 | 184 | 184 | 171(7,3) | τ(Φ + φ) (98) | ||
133 | 171 | 170 | 165(23,14) | 175 w | τ(θ-O-Φ) (96) | |
134 | 161 | 160 | 160(2,6) | 150 vw | 146 w | τ(θ) (56) + τ(θ-CH2OH) (29) + τ(θ-O-Φ) (11) |
135 | 132, 126 | 130 | 128(1,1) | 125 w | τ(θ-CH2OH) (49) + τ(HO-θ-OH) (43) | |
136 | 115 | 116 | 115(1,4) | 115 sh | τ(HO-θ-OH) (34) + τ(θ-CH2OH) (36)+ τ(θ-O-Φ) (23) | |
137 | 107 | 101 | 106(2,1) | τ(Φ-φ) (42) + τ(C-COOH)-Φ(33) | ||
138 | 102, 97 | 89 | 103(2.2) | τ(θ-COH) (49) + τ(θ-CH2) (45) | ||
139 | 78 | 80 | 82(0,3) | τ(Φ-COOH) (58) + τ(Φ) (44) | ||
140 | 73 | 72 | 74(0,5) | τ(Φ) (54) + ρ(C-COOH)-Φ(33) | ||
141 | 65 | 64 | 65(1,21) | τ(θ) (48) + ρ(COH)-θ(40) | ||
142 | 39 | 38 | 39(0,32) | τ(θ-Φ) (57) + ρ(COH)-φ(36) | ||
143 | 33 | 30 | 32(0,25) | τ(θ-Φφ(70) + τ(COH)-φ(19) | ||
144 | 24 | 22 | 21(0,100) | τ(θ-Φφ) (79) |
Atomic Numbering | Mulliken Atomic Charges | NBO Atomic Charge | Atomic Numbering | Mulliken Atomic Charges | NBO Atomic Charge |
---|---|---|---|---|---|
O1 | −0.548 | −0.591 | C26 | 0.251 | −0.015 |
O2 | −0.470 | −0.549 | H27 | 0.037 | 0.223 |
O3 | −0.503 | −0.749 | H28 | 0.058 | 0.225 |
O4 | −0.548 | −0.610 | H29 | 0.049 | 0.200 |
O5 | −0.522 | −0.736 | H30 | 0.035 | 0.161 |
O6 | −0.544 | −0.755 | H31 | 0.049 | 0.202 |
O7 | −0.545 | −0.748 | H32 | 0.047 | 0.211 |
O8 | −0.430 | −0.711 | H33 | 0.063 | 0.191 |
O9 | −0.430 | −0.633 | H34 | 0.061 | 0.197 |
O10 | −0.500 | −0.735 | H35 | 0.063 | 0.208 |
C11 | −0.083 | −0.245 | H36 | 0.057 | 0.192 |
C12 | −0.085 | −0224 | H37 | 0.002 | 0.144 |
C13 | −0.127 | −0.220 | H38 | 0.073 | 0.201 |
C14 | 0.278 | 0.166 | H39 | 0.057 | 0.196 |
C15 | −0.067 | −0.403 | H40 | 0.235 | 0.455 |
C16 | 0.591 | 0.456 | H41 | 0.022 | 0.157 |
C 17 | −0.201 | −0.255 | H42 | 0.036 | 0.169 |
C18 | −0.119 | −0.563 | H43 | 0.041 | 0.179 |
C19 | 0.473 | 0.437 | H44 | 0.033 | 0.160 |
C20 | 0.275 | 0.259 | H45 | 0.042 | 0.176 |
C21 | 0.246 | 0.095 | H46 | 0.247 | 0.454 |
C22 | 0.246 | 0.107 | H47 | 0.256 | 0.470 |
C23 | 0.275 | 0.115 | H48 | 0.263 | 0.470 |
C24 | 0.180 | 0.105 | H49 | 0.249 | 0.483 |
C25 | 0.594 | 0.822 | H50 | 0.243 | 0.455 |
No | Molecular Orbitals | Energy | Energy Gap | Ionization Potential I | Electron Affinity A | Global Hardness η | Chemical Potential μ | Electro-Negativity χ | Global Softness σ | Global Electrophilicity ω |
---|---|---|---|---|---|---|---|---|---|---|
[eV] | [eV] | [eV] | [eV] | [eV] | [eV] | [eV] | [eV] | [eV] | ||
1. | H | −6.62 | 5.68 | 6.62 | 0.94 | 2.84 | −3.78 | 3.78 | 0.18 | 2.52 |
L | −0.94 | |||||||||
2. | H − 1 | −7.30 | 7.74 | 7.30 | 0.44 | 3.87 | −3.43 | 3.43 | 0.13 | 1.53 |
L + 1 | 0.44 | |||||||||
3. | H − 2 | −7.42 | 8.15 | 7.42 | 0.73 | 4.08 | −3.35 | 3.35 | 0.12 | 1.38 |
L + 2 | 0.73 |
Electron Levels | eV | nm | cm−1 | Oscillator Strength |
---|---|---|---|---|
Singlets | ||||
S1 | 5.1236 | 241.99 | 41,324 | 0.0073 |
S2 | 5.3784 | 230.52 | 43,380 | 0.2038 |
S3 | 5.8312 | 212.62 | 47,032 | 0.0182 |
S4 | 5.8778 | 210.94 | 47,407 | 0.0516 |
S5 | 6.2700 | 197.74 | 50,571 | 0.0001 |
S6 | 6.3440 | 195.44 | 51,167 | 0.0008 |
S7 | 6.4366 | 192.62 | 51,916 | 0.0041 |
S8 | 6.5325 | 189.80 | 52,687 | 0.0020 |
S9 | 6.5971 | 187.94 | 53,208 | 0.0020 |
S10 | 6.6393 | 186.74 | 53,550 | 0.0004 |
Triplets | ||||
T1 | 3.4084 | 363.76 | 27,491 | 0.0000 |
T2 | 4.7521 | 260.90 | 38,329 | 0.0000 |
T3 | 5.5947 | 221.61 | 45,124 | 0.0000 |
T4 | 5.7579 | 215.33 | 46,440 | 0.0000 |
T5 | 5.8279 | 212.74 | 47,006 | 0.0000 |
T6 | 6.2618 | 198.00 | 50,505 | 0.0000 |
T7 | 6.3102 | 196.48 | 50,896 | 0.0000 |
T8 | 6.3757 | 194.46 | 51,424 | 0.0000 |
T9 | 6.4022 | 193.66 | 51,637 | 0.0000 |
T10 | 6.4411 | 192.49 | 51,951 | 0.0000 |
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Zając, A.; Michalski, J.; Ptak, M.; Dymińska, L.; Kucharska, A.Z.; Zierkiewicz, W.; Hanuza, J. Physicochemical Characterization of the Loganic Acid–IR, Raman, UV-Vis and Luminescence Spectra Analyzed in Terms of Quantum Chemical DFT Approach. Molecules 2021, 26, 7027. https://doi.org/10.3390/molecules26227027
Zając A, Michalski J, Ptak M, Dymińska L, Kucharska AZ, Zierkiewicz W, Hanuza J. Physicochemical Characterization of the Loganic Acid–IR, Raman, UV-Vis and Luminescence Spectra Analyzed in Terms of Quantum Chemical DFT Approach. Molecules. 2021; 26(22):7027. https://doi.org/10.3390/molecules26227027
Chicago/Turabian StyleZając, Adam, Jacek Michalski, Maciej Ptak, Lucyna Dymińska, Alicja Z. Kucharska, Wiktor Zierkiewicz, and Jerzy Hanuza. 2021. "Physicochemical Characterization of the Loganic Acid–IR, Raman, UV-Vis and Luminescence Spectra Analyzed in Terms of Quantum Chemical DFT Approach" Molecules 26, no. 22: 7027. https://doi.org/10.3390/molecules26227027