434:
17:
60:
332:
67:
Dithiocarbamates are anions. Because of the pi-donor properties of the amino substituent, the two sulfur centers show enhanced basicity. This situation is represented by the zwitterionic resonance structure that depicts a positive charge on N and negative charges on both sulfurs. This N to C
549:. Metal thiocarbamates are also used in metal-to-metal lubrication proposes, mainly as an anti-oxidation or anti-extreme pressure (EP) additive. 1-2% of such compounds can be added to internal combustion engine lubricant to increase extreme pressure performance in high operational temperatures.
72:
results in partial double bond character. Consequently, barriers to rotational about this bond are elevated. Another consequence of their high basicity, dithiocarbamates often stabilize complexes in uncharacteristically high oxidation state (e.g., Fe(IV), Co(IV), Ni(III), Cu(III)).
837:
Colapietro, M.; Vaciago, A.; Bradley, D. C.; Hursthouse, M. B.; Rendall, I. F. (1972). "Structural studies of metal dithiocarbamates. Part VI. The crystal and molecular structure of tetrakis(NN-diethyldithiocarbamato)titanium(IV)".
896:
Nagy, Eszter M.; Pettenuzzo, Andrea; Boscutti, Giulia; Marchiò, Luciano; Dalla Via, Lisa; Fregona, Dolores (2012). "Ruthenium(II/III)-Based
Compounds with Encouraging Antiproliferative Activity against Non-small-Cell Lung Cancer".
676:"Variation of M···H–C Interactions in Square-Planar Complexes of Nickel(II), Palladium(II), and Platinum(II) Probed by Luminescence Spectroscopy and X-ray Diffraction at Variable Pressure"
1549:
1586:
977:
1010:
Shah, Faiz Ullah; Glavatskih, Sergei; Antzutkin, Oleg N. (2012). "Novel
Alkylborate–Dithiocarbamate Lubricant Additives: Synthesis and Tribophysical Characterization".
1090:
1436:
1616:
152:
Dithiocarbamates are classified as derivatives of dithiocarbamic acid. Their properties as ligands resemble the conjugate bases of many related "1,1-dithioacids":
1653:
932:
Sarker, Jagodish C.; Hogarth, Graeme (2021). "Dithiocarbamate
Complexes as Single Source Precursors to Nanoscale Binary, Ternary and Quaternary Metal Sulfides".
446:
Dithiocarbamate complexes do not undergo characteristic reactions. They can be removed from complexes by oxidation, as illustrated by the iodination of the
721:
Wang, Chen; Niu, Jiao; Li, Jun; Ma, Xiaoxun (2017). "Synthesis, Structures and
Properties of Three Copper Complexes with Dibutyldithiocarbamate Ligand".
1743:
1467:
861:
Hendrickson, Alan R.; Martin, Raymond L.; Taylor, Donald (1975). "Synthesis and
Properties of Dimeric Cobalt(III) Dithiocarbamate Complexes [Co
1608:
675:
1416:
1287:
658:
1722:
1573:
1494:
1441:
1083:
810:
Elliot, R. L.; West, B. O.; Snow, M. R.; Tiekink, E. R. T. (1986). "A Second
Polymorph of Tris(N,N-diethyldithiocarbamato)manganese(III)".
674:
Poirier, Stéphanie; Lynn, Hudson; Reber, Christian; Tailleur, Elodie; Marchivie, Mathieu; Guionneau, Philippe; Probert, Michael R. (2018).
1459:
1411:
388:
357:
1734:
1689:
1645:
1629:
1431:
1398:
1388:
1275:
994:
536:
1775:
1684:
1541:
1340:
588:
529:
447:
420:
382:
21:
1637:
1600:
1595:
1561:
1403:
1352:
1317:
1300:
1292:
1228:
1168:
1045:
Shekarriz, Marzieh (2016). "An
Investigation of Antioxidant Properties of Zinc and Molybdenum Dithiocarbamates in Hydrocarbons".
414:
1446:
1219:
1207:
1178:
1173:
1076:
284:
1522:
1426:
1380:
1263:
1183:
1137:
756:
Zhu, H.-P.; Deng, Y.-H.; Huang, X.-Y.; Chen, C.-N.; Liu, Q.-T. (1997). "Tris(N,N-diethyldithiocarbamato-S,S')vanadium(III)".
621:
1195:
1714:
1536:
1250:
1806:
525:
1698:
1258:
1113:
194:
1486:
360:, palladium bis(dimethyldithiocarbamate), platinum bis(dimethyldithiocarbamate), all square-planar complexes
429:
diruthenium pentakis(diethyldithiocarbamate) cation, with a pair of octahedral Ru(III) centers, two isomers
1581:
1393:
1421:
567:
Coucouvanis, Dimitri (1979). "The
Chemistry of the Dithioacid and 1,1-Dithiolate Complexes, 1968–1977".
385:, ruthenium tris(diethyldithiocarbamate), osmium tris(diethyldithiocarbamate), all octahedral complexes
873:]: X-Ray Structural Analysis of Pentakis(diethyldithiocarbamato)dicobalt(III) Tetrafluoroborate".
391:, rhodium tris(diethyldithiocarbamate), iridium tris(diethyldithiocarbamate), all octahedral complexes
1372:
1099:
730:
32:
1762:
783:
Raston, CL; White, AH (1977). "Crystal
Structure of Tris(N,N-diethyldithiocarbamato)chromium(III)".
1780:
637:
Ileperuma, O. A.; Feltham, R. D. (1976). "Dithiocarbamate
Complexes of Iron and Cobalt Nitrosyls".
1785:
1767:
1513:
1118:
1027:
957:
703:
241:
990:
949:
914:
695:
654:
617:
584:
245:
178:
116:
A wide variety of secondary amines give the corresponding dtc ligand. Popular amines include
1054:
1019:
982:
941:
906:
878:
843:
819:
792:
765:
738:
687:
646:
609:
576:
288:
85:
81:
426:
dicobalt pentakis(diethyldithiocarbamate) cation, with a pair of octahedral Co(III) centers
165:
36:
734:
237:
In some cases, the dithiocarbamate serves as a reductant, followed by its complexation.
1531:
1245:
433:
1800:
1240:
1145:
961:
117:
1031:
707:
742:
540:
125:
43:
dtc. Many complexes are known. Several homoleptic derivatives have the formula M(R
986:
691:
1305:
945:
133:
1023:
823:
769:
650:
580:
613:
546:
511:
1058:
953:
918:
910:
699:
59:
16:
1068:
882:
847:
156:
76:
Dithiocarbamate salts are easily synthesized. Many primary and secondary
975:
Engels, Hans-Wilhelm; et al. "Rubber, 4. Chemicals and Additives".
69:
796:
515:
331:
519:
432:
77:
58:
812:
Acta Crystallographica Section C Crystal Structure Communications
758:
Acta Crystallographica Section C Crystal Structure Communications
604:
Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives".
1072:
379:
manganese tris(dimthylthtiocarbamate), an octahedral complex
373:
vanadium tris(diethyldithiocarbamate), an octahedral complex
376:
chromium tris(diethylditiocarbamate), an octahedral complex
363:
copper bis(diethyldithiocarbamate), a square-planar complex
63:
Main resonance structures of a dithiocarbamate anion.
875:
Journal of the Chemical Society, Dalton Transactions
840:
Journal of the Chemical Society, Dalton Transactions
1755:
1665:
1506:
1479:
1365:
1333:
1161:
1130:
1106:
193:Commonly, metal dithiocarbamates are prepared by
978:Ullmann's Encyclopedia of Industrial Chemistry
606:Ullmann's Encyclopedia of Industrial Chemistry
1084:
514:in the form of the iron and zinc derivatives
499:They degrade to metal sulfides upon heating.
8:
1047:Journal of Petroleum Science and Technology
404:molybdenum tetrakis(diethyldithiocarbamate)
1091:
1077:
1069:
401:titanium tetrakis(dimethyldithiocarbamate)
29:Transition metal dithiocarbamate complexes
507:Dtc complexes find several applications:
39:ligand, which are typically abbreviated R
492:
488:
484:
480:
476:
472:
468:
464:
460:
456:
330:
15:
559:
197:using alkali metal dithiocarbamates:
7:
571:. Progress in Inorganic Chemistry.
389:cobalt tris(diethyldithiocarbamate)
358:nickel bis(dimethyldithiocarbamate)
537:iron tris(dimethyldithiocarbamate)
14:
530:zinc bis(dimethyldithiocarbamate)
448:iron tris(diethyldithiocarbamate)
421:zinc bis(dimethyldithiocarbamate)
383:iron tris(diethyldithiocarbamate)
22:iron tris(diethyldithiocarbamate)
415:iron bis(diethyldithiocarbamate)
240:A complementary method entails
785:Australian Journal of Chemistry
285:tetrakis(dimethylamido)titanium
283:Metal amido complexes, such as
248:to low-valent metal complexes:
88:to form dithiocarbamate salts:
899:Chemistry - A European Journal
743:10.1016/j.molstruc.2017.01.021
723:Journal of Molecular Structure
1:
987:10.1002/14356007.a23_365.pub2
692:10.1021/acs.inorgchem.8b00724
946:10.1021/acs.chemrev.0c01183
1823:
526:vulcanization accelerators
423:, pentacoordinate Zn dimer
417:, pentacoordinate Fe dimer
1024:10.1007/s11249-011-9855-x
824:10.1107/S0108270186094635
770:10.1107/S0108270196015065
651:10.1002/9780470132470.ch2
581:10.1002/9780470166277.ch5
195:salt metathesis reactions
614:10.1002/14356007.a09_001
981:. Weinheim: Wiley-VCH.
608:. Weinheim: Wiley-VCH.
35:containing one or more
1100:Coordination complexes
1059:10.22078/jpst.2016.669
911:10.1002/chem.201202171
438:
348:
64:
55:Ligand characteristics
33:coordination complexes
25:
436:
334:
62:
19:
883:10.1039/dt9750002182
848:10.1039/DT9720001052
409:Dimetallic complexes
327:Homoleptic complexes
905:(45): 14464–14472.
735:2017JMoSt1135...75W
680:Inorganic Chemistry
639:Inorganic Syntheses
51:where n = 2 and 3.
439:
396:Tetrakis complexes
349:
246:thiuram disulfides
242:oxidative addition
179:Dithiocarboxylates
65:
26:
1794:
1793:
1012:Tribology Letters
940:(10): 6057–6123.
797:10.1071/CH9772091
686:(13): 7713–7723.
660:978-0-470-13178-7
569:Prog. Inorg. Chem
335:Structure of Ti(S
189:Synthetic methods
1814:
1807:Dithiocarbamates
1093:
1086:
1079:
1070:
1063:
1062:
1042:
1036:
1035:
1007:
1001:
1000:
972:
966:
965:
934:Chemical Reviews
929:
923:
922:
893:
887:
886:
858:
852:
851:
834:
828:
827:
807:
801:
800:
780:
774:
773:
753:
747:
746:
718:
712:
711:
671:
665:
664:
634:
628:
627:
601:
595:
594:
564:
495:
306:
289:carbon disulfide
278:
259:
232:
208:
166:Dithiophosphates
86:sodium hydroxide
82:carbon disulfide
1822:
1821:
1817:
1816:
1815:
1813:
1812:
1811:
1797:
1796:
1795:
1790:
1771:
1751:
1738:
1730:
1726:
1718:
1710:
1706:
1702:
1693:
1680:
1676:
1661:
1657:
1649:
1641:
1633:
1624:
1620:
1612:
1604:
1590:
1577:
1569:
1565:
1557:
1553:
1545:
1526:
1517:
1502:
1498:
1490:
1475:
1463:
1454:
1450:
1407:
1384:
1376:
1361:
1356:
1348:
1344:
1329:
1325:
1321:
1313:
1309:
1296:
1283:
1279:
1271:
1267:
1254:
1236:
1232:
1223:
1215:
1211:
1203:
1199:
1191:
1187:
1157:
1153:
1149:
1141:
1126:
1122:
1102:
1097:
1067:
1066:
1044:
1043:
1039:
1009:
1008:
1004:
997:
974:
973:
969:
931:
930:
926:
895:
894:
890:
872:
868:
864:
860:
859:
855:
836:
835:
831:
809:
808:
804:
782:
781:
777:
755:
754:
750:
720:
719:
715:
673:
672:
668:
661:
636:
635:
631:
624:
603:
602:
598:
591:
566:
565:
561:
556:
505:
494:
490:
486:
482:
478:
474:
470:
466:
462:
458:
454:
444:
346:
342:
338:
329:
322:
318:
314:
310:
304:
302:
298:
276:
274:
270:
266:
262:
257:
255:
230:
228:
224:
220:
216:
212:
206:
204:
191:
184:
175:
171:
162:
148:Related ligands
143:
139:
131:
123:
111:
107:
103:
100:+ NaOH → R
99:
95:
57:
50:
46:
42:
37:dithiocarbamate
12:
11:
5:
1820:
1818:
1810:
1809:
1799:
1798:
1792:
1791:
1789:
1788:
1783:
1778:
1773:
1769:
1765:
1759:
1757:
1756:Halide donors:
1753:
1752:
1750:
1749:
1741:
1736:
1732:
1728:
1724:
1720:
1716:
1712:
1708:
1704:
1700:
1696:
1691:
1687:
1682:
1678:
1674:
1669:
1667:
1663:
1662:
1660:
1659:
1655:
1651:
1647:
1643:
1639:
1635:
1631:
1627:
1622:
1618:
1614:
1610:
1606:
1602:
1598:
1593:
1588:
1584:
1579:
1575:
1571:
1567:
1563:
1559:
1555:
1551:
1547:
1543:
1539:
1534:
1529:
1524:
1520:
1515:
1510:
1508:
1504:
1503:
1501:
1500:
1496:
1492:
1488:
1483:
1481:
1477:
1476:
1474:
1473:
1465:
1461:
1457:
1452:
1448:
1444:
1439:
1434:
1429:
1424:
1419:
1414:
1409:
1405:
1401:
1396:
1391:
1386:
1382:
1378:
1374:
1369:
1367:
1363:
1362:
1360:
1359:
1354:
1350:
1346:
1342:
1337:
1335:
1331:
1330:
1328:
1327:
1323:
1319:
1315:
1311:
1307:
1303:
1298:
1294:
1290:
1285:
1281:
1277:
1273:
1269:
1265:
1261:
1256:
1252:
1248:
1243:
1238:
1234:
1230:
1226:
1221:
1217:
1213:
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1181:
1176:
1171:
1165:
1163:
1159:
1158:
1156:
1155:
1151:
1147:
1143:
1139:
1134:
1132:
1128:
1127:
1125:
1124:
1120:
1116:
1110:
1108:
1104:
1103:
1098:
1096:
1095:
1088:
1081:
1073:
1065:
1064:
1037:
1002:
996:978-3527306732
995:
967:
924:
888:
870:
866:
862:
853:
829:
818:(6): 763–764.
802:
775:
764:(6): 692–693.
748:
713:
666:
659:
629:
622:
596:
589:
558:
557:
555:
552:
551:
550:
544:
533:
523:
522:, respectively
504:
501:
497:
496:
443:
440:
431:
430:
427:
424:
418:
411:
410:
406:
405:
402:
398:
397:
393:
392:
386:
380:
377:
374:
370:
369:
368:Tris complexes
365:
364:
361:
354:
353:
344:
340:
336:
328:
325:
324:
323:
320:
316:
312:
308:
300:
296:
281:
280:
272:
268:
264:
260:
253:
235:
234:
226:
222:
218:
214:
210:
202:
190:
187:
186:
185:
182:
176:
173:
169:
163:
160:
150:
149:
141:
137:
129:
121:
114:
113:
109:
105:
101:
97:
93:
56:
53:
48:
44:
40:
13:
10:
9:
6:
4:
3:
2:
1819:
1808:
1805:
1804:
1802:
1787:
1784:
1782:
1779:
1777:
1774:
1772:
1766:
1764:
1761:
1760:
1758:
1754:
1748:
1747:
1742:
1740:
1733:
1731:
1721:
1719:
1713:
1711:
1697:
1695:
1688:
1686:
1683:
1681:
1671:
1670:
1668:
1664:
1658:
1652:
1650:
1644:
1642:
1636:
1634:
1628:
1626:
1615:
1613:
1607:
1605:
1599:
1597:
1594:
1592:
1585:
1583:
1580:
1578:
1572:
1570:
1560:
1558:
1548:
1546:
1540:
1538:
1535:
1533:
1530:
1528:
1521:
1519:
1512:
1511:
1509:
1505:
1499:
1493:
1491:
1485:
1484:
1482:
1478:
1472:
1470:
1466:
1464:
1458:
1456:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1402:
1400:
1397:
1395:
1392:
1390:
1387:
1385:
1379:
1377:
1371:
1370:
1368:
1364:
1358:
1351:
1349:
1339:
1338:
1336:
1332:
1326:
1316:
1314:
1304:
1302:
1299:
1297:
1291:
1289:
1286:
1284:
1274:
1272:
1262:
1260:
1257:
1255:
1249:
1247:
1244:
1242:
1239:
1237:
1227:
1225:
1218:
1216:
1206:
1204:
1194:
1192:
1182:
1180:
1177:
1175:
1172:
1170:
1167:
1166:
1164:
1160:
1154:
1144:
1142:
1136:
1135:
1133:
1129:
1123:
1117:
1115:
1112:
1111:
1109:
1105:
1101:
1094:
1089:
1087:
1082:
1080:
1075:
1074:
1071:
1060:
1056:
1052:
1048:
1041:
1038:
1033:
1029:
1025:
1021:
1017:
1013:
1006:
1003:
998:
992:
988:
984:
980:
979:
971:
968:
963:
959:
955:
951:
947:
943:
939:
935:
928:
925:
920:
916:
912:
908:
904:
900:
892:
889:
884:
880:
876:
857:
854:
849:
845:
841:
833:
830:
825:
821:
817:
813:
806:
803:
798:
794:
790:
786:
779:
776:
771:
767:
763:
759:
752:
749:
744:
740:
736:
732:
728:
724:
717:
714:
709:
705:
701:
697:
693:
689:
685:
681:
677:
670:
667:
662:
656:
652:
648:
644:
640:
633:
630:
625:
619:
615:
611:
607:
600:
597:
592:
590:9780470166277
586:
582:
578:
574:
570:
563:
560:
553:
548:
545:
542:
538:
534:
531:
527:
524:
521:
517:
513:
510:
509:
508:
502:
500:
453:
452:
451:
449:
441:
435:
428:
425:
422:
419:
416:
413:
412:
408:
407:
403:
400:
399:
395:
394:
390:
387:
384:
381:
378:
375:
372:
371:
367:
366:
362:
359:
356:
355:
352:Bis complexes
351:
350:
333:
326:
294:
293:
292:
290:
287:, react with
286:
251:
250:
249:
247:
243:
238:
200:
199:
198:
196:
188:
180:
177:
167:
164:
158:
155:
154:
153:
147:
146:
145:
135:
127:
119:
118:dimethylamine
91:
90:
89:
87:
83:
79:
74:
71:
61:
54:
52:
38:
34:
30:
23:
20:Structure of
18:
1745:
1672:
1468:
1050:
1046:
1040:
1015:
1011:
1005:
976:
970:
937:
933:
927:
902:
898:
891:
877:(21): 2182.
874:
856:
842:(10): 1052.
839:
832:
815:
811:
805:
788:
784:
778:
761:
757:
751:
726:
722:
716:
683:
679:
669:
642:
638:
632:
605:
599:
572:
568:
562:
541:nitric oxide
506:
503:Applications
498:
445:
437:Isomers of .
282:
239:
236:
192:
151:
126:diethylamine
115:
75:
66:
28:
27:
791:(9): 2091.
575:: 301–469.
483:I + 0.5 (S
134:pyrrolidine
80:react with
1417:amino acid
1334:Si donors:
623:3527306730
554:References
547:lubricants
543:scavenger.
535:medicine,
512:herbicides
70:pi-bonding
1666:S donors:
1507:O donors:
1480:P donors:
1442:porphyrin
1389:imidazole
1366:N donors:
1162:C donors:
1131:B donors:
1107:H donors:
1018:: 67–78.
962:233222937
729:: 75–81.
442:Reactions
157:Xanthates
132:NH), and
96:NH + CS
1801:Category
1032:98677629
954:33847480
919:23012112
708:48355413
700:29893549
471:→ Fe(S
467:+ 0.5 I
108:Na + H
1280:& C
731:Bibcode
645:: 5–8.
311:→ Ti(S
263:→ Mo(S
217:→ Ni(S
1188:＝CH-CH
1030:
993:
960:
952:
917:
706:
698:
657:
620:
587:
516:Ferbam
305:
295:Ti(NMe
277:
258:
252:Mo(CO)
231:
207:
168:, (RO)
159:, ROCS
78:amines
1179:HC(O)
1174:RC(O)
1053:(2).
1028:S2CID
958:S2CID
704:S2CID
539:as a
520:Zineb
181:, RCS
144:NH).
124:NH),
1582:acac
1554:/HCO
1437:bipy
1196:C(CH
991:ISBN
950:PMID
915:PMID
869:dtc)
727:1135
696:PMID
655:ISBN
618:ISBN
585:ISBN
518:and
487:CNEt
475:CNEt
459:CNEt
455:Fe(S
339:CNEt
315:CNMe
303:+ 4
275:+ 6
267:CNMe
256:+ 2
233:NaCl
229:+ 2
221:CNMe
213:CNMe
205:+ 2
201:NiCl
136:((CH
84:and
47:dtc)
31:are
1677:NCS
1654:OPR
1630:OSR
1609:ClO
1596:ONO
1574:RCO
1451:Si)
1447:(Me
1432:RCN
1399:RNO
1347:4−n
1345:SiR
1301:≡CR
1293:=CR
1288:RNC
1212:＝CH
1055:doi
1020:doi
983:doi
942:doi
938:121
907:doi
879:doi
844:doi
820:doi
793:doi
766:doi
739:doi
688:doi
647:doi
610:doi
577:doi
244:of
209:NaS
128:(Et
120:(Me
104:NCS
1803::
1781:Br
1776:Cl
1744:NC
1735:SR
1715:SO
1685:RS
1646:PO
1638:SO
1625:NO
1601:NO
1591:CO
1550:CO
1532:RO
1495:PR
1487:PR
1471:CS
1427:RN
1412:py
1404:NO
1394:NO
1373:NH
1357:Si
1282:70
1278:60
1251:CO
1246:CO
1241:CN
1220:RC
1208:CH
1184:CH
1138:BR
1049:.
1026:.
1016:45
1014:.
989:.
956:.
948:.
936:.
913:.
903:18
901:.
865:(R
816:42
814:.
789:30
787:.
762:53
760:.
737:.
725:.
702:.
694:.
684:57
682:.
678:.
653:.
643:16
641:.
616:.
583:.
573:26
528:,
450::
307:CS
291::
279:CO
172:PS
1786:I
1770:2
1768:F
1763:F
1746:S
1739:O
1737:2
1729:3
1727:O
1725:2
1723:S
1717:2
1709:2
1707:S
1705:2
1703:C
1701:2
1699:R
1694:S
1692:2
1690:R
1679:2
1675:2
1673:R
1656:3
1648:4
1640:4
1632:2
1623:5
1621:H
1619:5
1617:C
1611:4
1603:3
1589:2
1587:R
1576:2
1568:4
1566:O
1564:2
1562:C
1556:3
1552:3
1544:2
1542:O
1537:O
1527:O
1525:2
1523:R
1518:O
1516:2
1514:H
1497:2
1489:3
1469:N
1462:2
1460:N
1455:N
1453:2
1449:3
1422:N
1406:2
1383:3
1381:N
1375:3
1355:3
1353:R
1343:n
1341:H
1324:7
1322:H
1320:9
1318:C
1312:5
1310:H
1308:5
1306:C
1295:2
1276:C
1270:6
1268:R
1266:6
1264:C
1259:C
1253:2
1235:4
1233:H
1231:6
1229:C
1224:R
1222:2
1214:2
1210:2
1202:3
1200:)
1198:2
1190:2
1186:2
1169:R
1152:n
1150:H
1148:m
1146:B
1140:2
1121:2
1119:H
1114:H
1092:e
1085:t
1078:v
1061:.
1057::
1051:6
1034:.
1022::
999:.
985::
964:.
944::
921:.
909::
885:.
881::
871:5
867:2
863:2
850:.
846::
826:.
822::
799:.
795::
772:.
768::
745:.
741::
733::
710:.
690::
663:.
649::
626:.
612::
593:.
579::
532:.
493:2
491:)
489:2
485:2
481:2
479:)
477:2
473:2
469:2
465:3
463:)
461:2
457:2
347:.
345:4
343:)
341:2
337:2
321:4
319:)
317:2
313:2
309:2
301:4
299:)
297:2
273:4
271:)
269:2
265:2
261:2
254:6
227:2
225:)
223:2
219:2
215:2
211:2
203:2
183:2
174:2
170:2
161:2
142:4
140:)
138:2
130:2
122:2
112:O
110:2
106:2
102:2
98:2
94:2
92:R
49:n
45:2
41:2
24:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
