Synthesis and Ab Initio/DFT Studies on 2-(4-methoxyphenyl)benzo[d]thiazole
Abstract
:1. Introduction
2. Results and Discussion
2.1. Conformational stability
2.2. Molecular geometry
2.3. Vibrational assignments
3. Experimental Section
3.1. Synthesis of 2-(4-methoxyphenyl)benzothiazol
3.2. Instrumentation
3.3. Calculation details
Conformer | E (Hartree) | ΔE (kcal/mol) | Dipole moment (D) |
---|---|---|---|
1 | −1063.40977 | 0.0000 | 2.2783 |
2 | −1063.40973 | 0.0249 | 1.3747 |
Parameters | Calculated | Experimental | ||||
---|---|---|---|---|---|---|
HF | DFT | |||||
BLYP | B3LYP | B3PW91 | mPW1PW91 | |||
Bond lengths (Å) | ||||||
R(1,2) | 1.388 | 1.403 | 1.394 | 1.392 | 1.391 | 1.394(2)a |
R(1,6) | 1.378 | 1.401 | 1.390 | 1.388 | 1.386 | 1.384(2)a |
R(2,3) | 1.391 | 1.428 | 1.414 | 1.412 | 1.410 | 1.402(17)a |
R(2,12) | 1.743 | 1.767 | 1.750 | 1.740 | 1.737 | 1.7367(13)a |
R(3,4) | 1.393 | 1.411 | 1.401 | 1.399 | 1.397 | 1.3950(18)a |
R(3,11) | 1.382 | 1.387 | 1.379 | 1.374 | 1.373 | 1.3854(16)a |
R(4,5) | 1.377 | 1.397 | 1.387 | 1.384 | 1.382 | 1.381(2)a |
R(5,6) | 1.397 | 1.412 | 1.403 | 1.401 | 1.400 | 1.390(2)a |
R(11,13) | 1.270 | 1.308 | 1.295 | 1.295 | 1.293 | 1.3150(15)a |
R(12,13) | 1.766 | 1.822 | 1.792 | 1.778 | 1.772 | 1.764(4)a |
R(13,14) | 1.475 | 1.469 | 1.464 | 1.461 | 1.459 | 1.463(2)b |
R(14,15) | 1.394 | 1.416 | 1.405 | 1.402 | 1.400 | 1.400(4)c |
R(14,16) | 1.387 | 1.413 | 1.401 | 1.398 | 1.396 | 1.377(4)c |
R(15,17) | 1.374 | 1.392 | 1.383 | 1.381 | 1.379 | 1.381(4)c |
R(16,19) | 1.384 | 1.398 | 1.389 | 1.387 | 1.386 | 1.375(5)c |
R(17,21) | 1.392 | 1.412 | 1.402 | 1.400 | 1.398 | 1.391(4)c |
R(19,21) | 1.388 | 1.411 | 1.400 | 1.398 | 1.396 | 1.376(5)c |
R(21,24) | 1.341 | 1.374 | 1.359 | 1.353 | 1.350 | 1.352(4)c |
R(24,25) | 1.401 | 1.442 | 1.423 | 1.416 | 1.412 | 1.424(4)c |
Bond angles (o) | ||||||
A(2,1,6) | 118.08 | 118.16 | 118.12 | 118.05 | 118.03 | 117.95(14)a |
A(1,2,3) | 121.65 | 121.50 | 121.54 | 121.61 | 121.62 | 121.44(12)a |
A(1,2,12) | 129.51 | 129.12 | 129.28 | 129.27 | 129.29 | 129.55(10)a |
A(3,2,12) | 108.84 | 109.39 | 109.18 | 109.12 | 109.09 | 109.01(9)a |
A(2,3,4) | 119.73 | 119.26 | 119.37 | 119.33 | 119.35 | 119.31(1)a |
A(2,3,11) | 115.26 | 115.51 | 115.35 | 115.33 | 115.34 | 115.97(11)a |
A(4,3,11) | 125.00 | 125.23 | 125.28 | 125.34 | 125.31 | 124.70(11)a |
A(3,4,5) | 118.86 | 119.20 | 119.12 | 119.10 | 119.08 | 119.31(13)a |
A(4,5,6) | 120.90 | 120.87 | 120.88 | 120.92 | 120.92 | 120.74(14)a |
A(1,6,5) | 120.78 | 121.01 | 120.97 | 121.00 | 121.00 | 121.22(14)a |
A(3,11,13) | 112.11 | 112.43 | 112.21 | 111.89 | 111.78 | 110.72(10)a |
A(2,12,13) | 88.78 | 88.38 | 88.66 | 88.85 | 88.88 | 89.50(6)a |
A(11,13,12) | 115.01 | 114.30 | 114.59 | 114.80 | 114.92 | 114.78(9)a |
A(11,13,14) | 123.50 | 124.51 | 124.16 | 124.07 | 123.95 | 122.78(19)b |
A(12,13,14) | 121.49 | 121.19 | 121.26 | 121.13 | 121.13 | 121.84(15)b |
A(13,14,15) | 122.42 | 122.64 | 122.53 | 122.51 | 122.46 | 121.80(17)b |
A(13,14,16) | 119.38 | 119.35 | 119.30 | 119.24 | 119.21 | 119.73(18)b |
A(15,14,16) | 118.20 | 118.01 | 118.17 | 118.25 | 118.33 | 118.48(17)b |
A(14,15,17) | 121.07 | 121.13 | 121.05 | 121.02 | 120.98 | 119.71(18)b |
A(14,16,19) | 121.36 | 121.37 | 121.30 | 121.26 | 121.22 | 121.56(19)b |
A(15,17,21) | 120.19 | 120.23 | 120.23 | 120.21 | 120.19 | 120.0(3)c |
A(16,19,21) | 119.74 | 119.81 | 119.81 | 119.80 | 119.78 | 120.0(3)c |
A(17,21,19) | 119.45 | 119.45 | 119.45 | 119.46 | 119.50 | 118.9(3)c |
A(17,21,24) | 115.93 | 115.54 | 115.79 | 115.86 | 115.88 | 115.8(3)c |
A(19,21,24) | 124.62 | 125.00 | 124.75 | 124.68 | 124.62 | 125.1(3)c |
A(21,24,25) | 120.11 | 118.40 | 118.70 | 118.37 | 118.30 | 118.3(3)c |
No | Exp. | HF | DFT | Assignments, PED (%)g | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
BLYP | B3LYP | B3PW91 | mPW1PW91 | ||||||||||||||
Wave numbera | Rel. Inten. | Wave numbera | Rel. Inten. | Wave numbera | Rel. Inten. | Wave numbera | Rel. Inten. | Wave numbera | Rel. Inten. | ||||||||
Unscal. | Scaledb | Unscal. | Scaledc | Unscal. | Scaledd | Unscal. | Scalede | Unscal. | Scaledf | ||||||||
1 | 3111 | 3380 | 3059 | 2 | 3131 | 3110 | 4 | 3211 | 3108 | 3 | 3219 | 3101 | 3 | 3238 | 3098 | 3 | νCH, sym, ring 1, (99) |
2 | 3084 | 3363 | 3044 | 1 | 3118 | 3097 | 2 | 3198 | 3095 | 1 | 3210 | 3092 | 4 | 3229 | 3090 | 4 | νCH, asym, ring 1, (93) |
3 | 3084 | 3362 | 3043 | 1 | 3117 | 3097 | 6 | 3198 | 3095 | 5 | 3210 | 3091 | 1 | 3229 | 3089 | 1 | νCH, sym, ring 2, (87) |
4 | 3084 | 3359 | 3040 | 3 | 3117 | 3096 | 5 | 3197 | 3094 | 2 | 3205 | 3087 | 1 | 3224 | 3084 | 1 | νCH, asym, ring 1, (89) |
5 | 3084 | 3351 | 3033 | 5 | 3110 | 3090 | 9 | 3190 | 3088 | 6 | 3203 | 3085 | 5 | 3223 | 3083 | 5 | νCH, asym, ring 2, (99) |
6 | 3076 | 3338 | 3021 | 2 | 3100 | 3079 | 4 | 3180 | 3078 | 2 | 3192 | 3075 | 2 | 3212 | 3073 | 2 | νCH, asym, ring 2, (100) |
7 | 3076 | 3337 | 3020 | 2 | 3093 | 3073 | 3 | 3172 | 3070 | 3 | 3180 | 3063 | 1 | 3200 | 3061 | 1 | νCH, asym, ring 1, (100) |
8 | 3062 | 3324 | 3008 | 0 | 3088 | 3068 | 0 | 3168 | 3066 | 0 | 3180 | 3063 | 2 | 3198 | 3060 | 3 | νCH, asym, ring 2, (95) |
9 | 3034 | 3289 | 2977 | 9 | 3061 | 3041 | 9 | 3137 | 3037 | 8 | 3152 | 3036 | 7 | 3171 | 3034 | 8 | νCH, asym, CH3, (92) |
10 | 2968 | 3230 | 2923 | 10 | 2988 | 2969 | 15 | 3067 | 2969 | 12 | 3082 | 2969 | 11 | 3100 | 2966 | 12 | νCH, asym, CH3, (100) |
11 | 2910 | 3167 | 2867 | 11 | 2932 | 2912 | 29 | 3007 | 2911 | 21 | 3015 | 2904 | 21 | 3032 | 2901 | 22 | νCH, sym, CH3, (92) |
12 | 1604 | 1797 | 1627 | 43 | 1585 | 1574 | 63 | 1651 | 1598 | 62 | 1666 | 1604 | 66 | 1681 | 1608 | 73 | νC=C, ring 1, (43) |
13 | 1591 | 1790 | 1620 | 4 | 1571 | 1560 | 2 | 1638 | 1586 | 2 | 1653 | 1592 | 2 | 1669 | 1597 | 2 | νC=C, ring 2, (59) + νCN (10) |
14 | 1571 | 1759 | 1592 | 11 | 1540 | 1530 | 2 | 1608 | 1556 | 3 | 1623 | 1563 | 4 | 1639 | 1568 | 4 | νC=C, ring 1, (42) + δCCC (12) |
15 | 1558 | 1749 | 1583 | 1 | 1533 | 1523 | 2 | 1597 | 1546 | 2 | 1611 | 1551 | 2 | 1626 | 1555 | 2 | νC=C, ring 2, (57) + νCN (13) |
16 | 1521 | 1728 | 1564 | 13 | 1495 | 1485 | 8 | 1560 | 1510 | 5 | 1575 | 1517 | 6 | 1591 | 1522 | 7 | νCN (38)+νCC (12)+ δCCC (23) |
17 | 1483 | 1676 | 1517 | 55 | 1471 | 1462 | 22 | 1533 | 1483 | 67 | 1540 | 1483 | 77 | 1552 | 1485 | 89 | νCN (31) + δCH3, deform. (26) |
18 | 1467 | 1630 | 1476 | 9 | 1463 | 1453 | 58 | 1505 | 1457 | 24 | 1501 | 1445 | 23 | 1509 | 1444 | 24 | νCN (12) + δCH3, deform. (58) |
19 | 1454 | 1622 | 1468 | 1 | 1453 | 1444 | 3 | 1494 | 1446 | 3 | 1493 | 1438 | 3 | 1504 | 1439 | 3 | δCH3, deform. (91) |
20 | 1442 | 1609 | 1457 | 4 | 1440 | 1430 | 3 | 1489 | 1441 | 3 | 1489 | 1434 | 3 | 1497 | 1432 | 3 | νCC, ring 2, (26) + δCH (47) |
21 | 1433 | 1608 | 1455 | 8 | 1435 | 1426 | 12 | 1480 | 1433 | 6 | 1475 | 1421 | 4 | 1484 | 1420 | 3 | δCH3, umbrella (76) |
22 | 1412 | 1600 | 1448 | 12 | 1413 | 1404 | 9 | 1465 | 1418 | 12 | 1470 | 1415 | 11 | 1481 | 1416 | 14 | δCH, ring 2, (45) |
23 | 1400 | 1560 | 1412 | 3 | 1404 | 1394 | 9 | 1450 | 1404 | 5 | 1456 | 1402 | 3 | 1465 | 1402 | 3 | νCC, ring 1, (40) + δCH (13) |
24 | 1309 | 1448 | 1310 | 6 | 1312 | 1304 | 3 | 1346 | 1303 | 2 | 1369 | 1318 | 5 | 1377 | 1317 | 5 | νCC, ring 2, (52) |
25 | 1303 | 1422 | 1287 | 100 | 1307 | 1299 | 27 | 1342 | 1299 | 39 | 1366 | 1316 | 28 | 1375 | 1315 | 35 | νCC, ring 1, (53) |
26 | 1286 | 1414 | 1280 | 1 | 1297 | 1288 | 1 | 1334 | 1291 | 1 | 1329 | 1280 | 15 | 1340 | 1282 | 25 | δCH, ring 1, (80) |
27 | 1267 | 1372 | 1242 | 11 | 1272 | 1264 | 3 | 1316 | 1273 | 9 | 1325 | 1276 | 10 | 1333 | 1275 | 11 | νCC,ring 2, (13)+δCH (15)+νCN(19) |
28 | 1253 | 1367 | 1237 | 8 | 1235 | 1227 | 21 | 1289 | 1247 | 100 | 1302 | 1254 | 100 | 1314 | 1257 | 100 | νCN (13) + δCH (18), ring 2 |
29 | 1224 | 1335 | 1208 | 1 | 1229 | 1221 | 100 | 1274 | 1234 | 3 | 1277 | 1230 | 2 | 1285 | 1230 | 2 | νCO (39) + δCH (20), ring 1 |
30 | 1207 | 1322 | 1196 | 11 | 1201 | 1193 | 15 | 1250 | 1210 | 24 | 1262 | 1216 | 18 | 1274 | 1219 | 20 | νCN (21) + νCC (29) |
31 | 1170 | 1287 | 1165 | 29 | 1168 | 1160 | 1 | 1206 | 1167 | 1 | 1205 | 1160 | 1 | 1213 | 1160 | 2 | δCH, (74) |
32 | 1157 | 1282 | 1161 | 1 | 1158 | 1151 | 83 | 1193 | 1155 | 51 | 1190 | 1146 | 38 | 1196 | 1145 | 40 | δCH (51), ring 1 |
33 | 1141 | 1270 | 1149 | 2 | 1155 | 1147 | 0 | 1183 | 1145 | 1 | 1183 | 1139 | 2 | 1188 | 1137 | 2 | δCH (73), ring 2 |
34 | 1122 | 1240 | 1122 | 2 | 1130 | 1123 | 0 | 1171 | 1134 | 0 | 1171 | 1128 | 0 | 1179 | 1128 | 0 | δCH3, rock. (99) |
35 | 1114 | 1209 | 1094 | 1 | 1110 | 1103 | 2 | 1144 | 1107 | 2 | 1146 | 1104 | 2 | 1153 | 1103 | 2 | νCC (28) + δCH (32), ring 2 |
36 | 1084 | 1200 | 1087 | 2 | 1108 | 1100 | 5 | 1139 | 1102 | 4 | 1136 | 1094 | 4 | 1141 | 1092 | 4 | δCH (29), ring 1 |
37 | 1037 | 1174 | 1062 | 7 | 1040 | 1033 | 3 | 1082 | 1048 | 2 | 1089 | 1049 | 2 | 1098 | 1050 | 3 | νSC (22) + δCCC (46) |
38 | 1026 | 1169 | 1058 | 5 | 1007 | 1000 | 3 | 1060 | 1026 | 20 | 1079 | 1039 | 18 | 1093 | 1046 | 18 | νCC (29) + δCH (52), ring 2 |
39 | 1010 | 1107 | 1002 | 1 | 997 | 990 | 13 | 1039 | 1005 | 2 | 1043 | 1005 | 2 | 1050 | 1005 | 2 | νCC (11) + νO-CH3 (45) |
40 | 985 | 1104 | 999 | 0 | 993 | 986 | 15 | 1026 | 993 | 1 | 1026 | 988 | 1 | 1033 | 988 | 1 | νO-CH3 (30) + δCCC (55) |
41 | 968 | 1104 | 999 | 0 | 946 | 940 | 0 | 989 | 957 | 0 | 990 | 953 | 0 | 998 | 955 | 0 | γCH, (85), ring 2 |
42 | 947 | 1103 | 998 | 1 | 943 | 936 | 0 | 985 | 953 | 0 | 983 | 947 | 0 | 992 | 949 | 0 | γCH, (89), ring 1 |
43 | 941 | 1072 | 970 | 0 | 927 | 921 | 25 | 970 | 939 | 20 | 976 | 940 | 18 | 985 | 942 | 19 | νCC (11) +δCNC (34) + δCCN (11) |
44 | 925 | 1069 | 967 | 0 | 916 | 910 | 0 | 957 | 926 | 0 | 956 | 921 | 0 | 964 | 922 | 0 | γCH, (86), ring 1 |
45 | 910 | 1058 | 958 | 10 | 906 | 900 | 1 | 950 | 919 | 0 | 952 | 916 | 0 | 960 | 918 | 1 | γCH, (81), ring 2 |
46 | 858 | 968 | 876 | 0 | 845 | 839 | 0 | 873 | 845 | 0 | 876 | 844 | 0 | 882 | 844 | 0 | νCN (12) + δCCC (32) |
47 | 831 | 942 | 853 | 14 | 830 | 825 | 1 | 866 | 838 | 1 | 866 | 834 | 1 | 873 | 835 | 1 | γCH, (87), ring 2 |
48 | 815 | 930 | 842 | 1 | 812 | 807 | 19 | 848 | 821 | 18 | 847 | 816 | 19 | 854 | 817 | 20 | γCH, (49), ring 1 |
49 | 791 | 918 | 831 | 0 | 787 | 782 | 0 | 822 | 795 | 0 | 821 | 791 | 0 | 828 | 793 | 0 | γCH, (98), ring 1 |
50 | 779 | 866 | 784 | 2 | 774 | 769 | 3 | 805 | 780 | 3 | 811 | 781 | 3 | 818 | 782 | 3 | νCN (34) +νCO (20) |
51 | 756 | 852 | 771 | 13 | 742 | 738 | 16 | 772 | 747 | 14 | 772 | 744 | 15 | 778 | 744 | 17 | γCH, (53), ring 2+ γC, (17) |
52 | 729 | 812 | 735 | 4 | 710 | 705 | 6 | 738 | 714 | 7 | 737 | 709 | 7 | 742 | 710 | 7 | γC (21) + γCH, (10) |
53 | 709 | 797 | 722 | 0 | 705 | 701 | 2 | 732 | 708 | 1 | 730 | 703 | 1 | 735 | 704 | 1 | γC, (46) |
54 | 692 | 771 | 698 | 0 | 690 | 686 | 1 | 717 | 694 | 0 | 721 | 694 | 0 | 726 | 695 | 0 | νCS (23) + δCCC (47) |
55 | 662 | 748 | 677 | 4 | 658 | 654 | 4 | 689 | 667 | 6 | 697 | 671 | 7 | 704 | 673 | 8 | δCCC (33) + δCCN (16) |
56 | 623 | 689 | 624 | 2 | 619 | 615 | 1 | 640 | 619 | 4 | 639 | 615 | 6 | 643 | 615 | 6 | δCCC (54) |
57 | 617 | 688 | 623 | 3 | 611 | 607 | 11 | 635 | 614 | 5 | 634 | 611 | 1 | 638 | 610 | 1 | δCNC (11) + δCCN (11) + δCCC (26) |
58 | 605 | 680 | 615 | 1 | 600 | 596 | 1 | 625 | 605 | 1 | 626 | 603 | 1 | 631 | 604 | 1 | γC (52) + τCN (25) |
59 | 551 | 613 | 555 | 2 | 546 | 543 | 12 | 564 | 546 | 8 | 562 | 542 | 7 | 565 | 541 | 8 | δCCC (15) + δCCO (15) + δCOC (18) |
60 | 540 | 604 | 546 | 4 | 540 | 536 | 2 | 561 | 543 | 2 | 560 | 539 | 2 | 564 | 539 | 2 | τCC (26) + γC (10) |
61 | - | 566 | 512 | 2 | 494 | 491 | 3 | 514 | 498 | 3 | 514 | 495 | 3 | 518 | 496 | 3 | τCN (10) + γC (35) |
62 | - | 550 | 497 | 0 | 490 | 486 | 1 | 509 | 493 | 0 | 512 | 493 | 0 | 516 | 494 | 0 | νCS (30) + δCCC (28) + δSCC (19) |
63 | - | 507 | 459 | 0 | 460 | 457 | 0 | 476 | 461 | 0 | 476 | 459 | 0 | 480 | 459 | 0 | δC-O-CH3 (25) +δCCC (10)+δCCO (15) |
64 | - | 482 | 436 | 1 | 422 | 419 | 2 | 438 | 424 | 1 | 436 | 420 | 2 | 439 | 420 | 2 | τCC (81), ring 2 |
65 | - | 459 | 416 | 0 | 406 | 403 | 0 | 421 | 407 | 0 | 422 | 406 | 1 | 425 | 407 | 1 | τCC (93), ring 1 |
66 | - | 451 | 408 | 1 | 399 | 396 | 0 | 418 | 405 | 0 | 419 | 403 | 0 | 422 | 403 | 0 | δSCC (38) + δCCN (12) |
67 | - | 398 | 360 | 0 | 349 | 347 | 0 | 363 | 352 | 0 | 364 | 350 | 0 | 367 | 351 | 0 | τCN (101) + τCC (26) |
68 | - | 349 | 316 | 1 | 314 | 312 | 1 | 326 | 315 | 1 | 326 | 314 | 1 | 329 | 314 | 1 | δCCN (19) + δCCC (21) + δCOC (16) |
69 | - | 300 | 272 | 0 | 262 | 260 | 0 | 274 | 265 | 0 | 275 | 264 | 0 | 277 | 265 | 0 | τCO (17) + τCC (17) + τCN (18) |
70 | - | 267 | 242 | 0 | 245 | 243 | 1 | 252 | 244 | 1 | 253 | 244 | 1 | 255 | 244 | 1 | τCC (18) + δCCC (22) + δCCO (11) |
71 | - | 252 | 228 | 0 | 219 | 217 | 0 | 230 | 222 | 0 | 232 | 223 | 0 | 234 | 224 | 0 | τCO (47) |
72 | - | 227 | 206 | 0 | 205 | 204 | 0 | 213 | 206 | 0 | 214 | 206 | 0 | 216 | 207 | 0 | δCNC (15) + δOCC (22) + δCOC (21) |
73 | - | 209 | 189 | 0 | 185 | 184 | 1 | 192 | 186 | 0 | 193 | 186 | 1 | 194 | 186 | 1 | τCC (57) + γC (30) |
74 | - | 147 | 133 | 1 | 136 | 135 | 1 | 140 | 136 | 1 | 142 | 137 | 1 | 143 | 137 | 1 | τCC (22) + τCO (31) |
75 | - | 90 | 81 | 0 | 92 | 91 | 0 | 93 | 90 | 0 | 94 | 91 | 0 | 95 | 91 | 0 | τCN (13) + τCO (51) |
76 | - | 87 | 79 | 0 | 81 | 80 | 0 | 83 | 81 | 0 | 83 | 79 | 0 | 83 | 79 | 0 | δCNC (42) + δCCC (38) |
77 | - | 47 | 42 | 0 | 43 | 43 | 0 | 45 | 43 | 0 | 45 | 43 | 0 | 45 | 43 | 0 | τCC (11) + τCN (35) +γC (26) |
78 | - | 17 | 16 | 0 | 30 | 30 | 0 | 29 | 28 | 0 | 30 | 29 | 0 | 31 | 30 | 0 | τCC (91) |
HF | BLYP | B3LYP | B3PW91 | mPW1PW91 | ||||||
---|---|---|---|---|---|---|---|---|---|---|
Mean absolute deviation | 153.80 | 23.14 | 12.90 | 12.90 | 48.68 | 6.62 | 54.13 | 7.14 | 64.50 | 7.46 |
RMSmol | 167.10 | 28.19 | 17.37 | 16.25 | 57.50 | 8.73 | 64.00 | 9.02 | 75.23 | 9.22 |
RMSover | 146.56 | 24.72 | 15.23 | 14.25 | 50.43 | 7.65 | 56.13 | 7.91 | 65.98 | 8.09 |
Scaling Factor | 1.0000 | 0.9051 | 1.0000 | 0.9934 | 1.0000 | 0.9679 | 1.0000 | 0.9631 | 1.0000 | 0.9567 |
r | 0.9997 | 0.9999 | 0.9999 | 0.9999 | 0.9999 |
Acknowledgements
References
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Arslan, H.; Algül, Ö. Synthesis and Ab Initio/DFT Studies on 2-(4-methoxyphenyl)benzo[d]thiazole. Int. J. Mol. Sci. 2007, 8, 760-776. https://doi.org/10.3390/i8080760
Arslan H, Algül Ö. Synthesis and Ab Initio/DFT Studies on 2-(4-methoxyphenyl)benzo[d]thiazole. International Journal of Molecular Sciences. 2007; 8(8):760-776. https://doi.org/10.3390/i8080760
Chicago/Turabian StyleArslan, Hakan, and Öztekin Algül. 2007. "Synthesis and Ab Initio/DFT Studies on 2-(4-methoxyphenyl)benzo[d]thiazole" International Journal of Molecular Sciences 8, no. 8: 760-776. https://doi.org/10.3390/i8080760