33:
285:
160:
Sulfides are characterized by their strong odors, which are similar to thiol odor. This odor limits the applications of volatile sulfides. In terms of their physical properties they resemble ethers, but are less volatile, higher melting, and less hydrophilic. These properties follow from the
184:
into the π-system. As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. Upon
82:
suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.
704:
is useful for stoichiometric reactions in organic synthesis whereas molybdenum-based catalysts are used to "sweeten" petroleum fractions, in the process called
347:
Such reactions are usually conducted in the presence of a base, which converts the thiol into the more nucleophilic thiolate. Analogously, the reaction of
90:
Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH
1106:
2025:
1068:
Brendsma, L.; Arens, J. F. (1967). "The chemistry of thioethers; differences and analogies with ethers". In Patai, Saul (ed.).
2030:
971:
908:
D. Landini; F. Rolla (1978). "Sulfide
Synthesis In Preparation Of Dialkyl And Alkyl Aryl Sulfides: Neopentyl Phenyl Sulfide".
788:
780:
661:
981:
757:
881:
Chauhan, Pankaj; Mahajan, Suruchi; Enders, Dieter (2014). "Organocatalytic Carbon–Sulfur Bond-Forming
Reactions".
776:
Systematic
Nomenclature of Organic Chemistry: A Directory to Comprehension and Application of its Basic Principles
1099:
1929:
449:
An unusual but well tested method for the synthesis of thioethers involves addition of alkenes, especially
149:
Sulfide is an angular functional group, the C–S–C angle approaching 90° The C–S bonds are about 180
1072:. The Chemistry of Functional Groups. London: Interscience / William Clowes and Sons. pp. 555–559.
153:. For the prototype, dimethylsulfide, the C-S-C angles is 99°, which is smaller than the C-O-C angle in
2058:
1502:
1092:
78:
except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the
513:
458:
71:
17:
1539:
673:
102:. Some sulfides are named by modifying the common name for the corresponding ether. For example, C
2012:
216:
1912:
774:
410:
161:
polarizability of the divalent sulfur center, which is greater than that for oxygen in ethers.
2019:
1907:
508:
lone pairs on sulfur dominate the sulfides' reactivity. Sulfides readily alkylate to stable
428:
352:
305:
227:
173:
413:. Trialkysulfonium salts react with nucleophiles with a dialkyl sulfide as a leaving group:
1988:
1433:
705:
372:
Alternatively, sulfides can be synthesized by the addition of a thiol to an alkene in the
8:
2053:
1294:
749:
189:
664:. Consequently Lewis acids do not decompose thioethers as they do ethers. Sulfides are
373:
1978:
1948:
1706:
1328:
1073:
977:
952:
935:
Hoyle, Charles E.; Bowman, Christopher N. (2010-02-22). "Thiol-Ene Click
Chemistry".
784:
753:
567:
454:
41:
1683:
1177:
1115:
944:
917:
890:
861:
716:
571:
366:
334:
63:
1902:
1661:
1656:
1639:
1622:
1423:
1172:
289:
137:
The modern systematic nomenclature in chemistry for the trival name thioether is
99:
49:
32:
1973:
1968:
1844:
1839:
1834:
1627:
1594:
1378:
1360:
1350:
680:
423:
This reaction is exploited in biological systems as a means of transferring an
403:
278:
79:
2047:
1993:
1941:
1872:
1758:
1748:
1743:
1733:
1728:
1678:
1673:
1589:
1584:
1574:
1428:
1383:
1345:
1333:
1304:
1182:
921:
185:
180:
character, they are non-nucleophilic. The nonbonding electrons on sulfur are
1924:
1811:
1806:
1783:
1534:
1373:
1299:
1236:
1231:
1209:
1165:
1150:
1140:
956:
948:
701:
439:
399:
60:
1983:
1936:
1897:
1778:
1666:
1651:
1646:
1634:
1199:
1194:
1160:
1155:
1145:
1123:
866:
849:
505:
462:
435:
115:
1892:
1883:
1763:
1718:
1614:
1579:
1569:
1509:
1445:
1368:
1316:
318:
297:
293:
231:
212:
209:
181:
894:
1859:
1773:
1738:
1723:
1711:
1554:
1529:
1338:
669:
660:
In analogy to their easy alkylation, sulfides bind to metals to form
547:
509:
348:
330:
223:
169:
150:
36:
General structure of a sulfide with the blue marked functional group.
1084:
1867:
1821:
1788:
1484:
1390:
1264:
1219:
1204:
450:
284:
177:
1829:
1753:
1604:
1599:
1564:
1549:
1544:
1514:
1497:
1321:
1248:
1214:
555:
409:
Sulfides can also be prepared by many other methods, such as the
326:
274:
119:
1077:
1050:
1026:
70:
as shown on right. Like many other sulfur-containing compounds,
1917:
1849:
1693:
1402:
1395:
1289:
1270:
1259:
1243:
1189:
724:
720:
712:
301:
219:
1798:
1768:
1701:
1559:
1524:
1519:
1492:
1440:
1407:
1311:
1135:
668:
ligands, but their affinity for metals is lower than typical
424:
325:. Alkylating agents include not only alkyl halides, but also
322:
154:
75:
1038:
1014:
727:
atom are labile, and can be deprotonated with strong bases.
1226:
1002:
990:
665:
973:
Weapons of mass casualties and terrorism response handbook
963:
226:
contains many organosulfur compounds, including sulfides.
157:(~110°). The C-S distance in dimethylsulfide is 1.81 Å.
114:
is methyl phenyl sulfide, but is more commonly called
827:
substituted at both ends are named substitutively as
74:
sulfides have foul odors. A sulfide is similar to an
880:
969:
847:
907:
457:. This method has been used in the production of
208:Sulfides are important in biology, notably in the
200:S, which indeed does behave as a typical sulfide.
2045:
823:, in the same way as their ether counterparts.
554:), which can themselves be further oxidized to
766:
203:
1100:
1067:
1056:
1044:
1032:
1020:
1008:
996:
850:"The Molecular Structure of Dimethyl Sulfide"
118:, since its structure is related to that for
848:Iijima, T.; Tsuchiy, S.; Kimura, M. (1977).
365:Analogous reactions are known starting with
934:
715:, thioethers are stable in the presence of
144:
1107:
1093:
976:. Boston: Jones and Bartlett. p. 47.
772:
672:. Chelating thioethers are known, such as
172:are a special class of sulfide-containing
865:
746:An Introduction to Organosulfur Chemistry
283:
31:
937:Angewandte Chemie International Edition
743:
570:is a typical oxidant—for example, with
14:
2046:
277:(i.e. natural gas) via the process of
230:is a useful high temperature plastic.
1114:
1088:
807:derivatives, respectively (formerly:
799:can again most uniformly be named as
781:Springer Science & Business Media
398:This reaction is often catalysed by
683:in the presence of certain metals:
317:Sulfides are typically prepared by
24:
1070:The Chemistry of the Ether Linkage
27:Organic compound with an –S– group
25:
2070:
773:Hellwinkel, Dieter (2012-12-06).
795:Individual species of the genus
546:Sulfides also oxidize easily to
288:Selected thioethers, from left:
85:
928:
901:
874:
841:
737:
312:
304:, and the engineering plastic
13:
1:
815:derivatives, respectively).
730:
164:
970:Stewart, Charles D. (2006).
819:(thioethers) are treated as
499:
360:RCLi + RS-SR → RCSR + RSLi
7:
204:Occurrence and applications
10:
2075:
2002:
1961:
1881:
1858:
1820:
1797:
1692:
1613:
1483:
1460:
1416:
1359:
1282:
1257:
1122:
1057:Brendsma & Arens 1967
1045:Brendsma & Arens 1967
1033:Brendsma & Arens 1967
1021:Brendsma & Arens 1967
1009:Brendsma & Arens 1967
997:Brendsma & Arens 1967
514:trimethylsulfonium iodide
459:bis(2-chloroethyl)sulfide
342:RBr + HSR' → RSR' + HBr
922:10.15227/orgsyn.058.0143
674:1,4,7-trithiacyclononane
453:across the S-Cl bond of
145:Structure and properties
2013:chemical classification
744:Cremlyn, R. J. (1996).
949:10.1002/anie.200903924
418:Nu + RS → Nu-R + RSR
411:Pummerer rearrangement
353:organolithium reagents
309:
273:, is the precursor to
174:heterocyclic compounds
66:with the connectivity
37:
2020:chemical nomenclature
355:produces thioethers:
306:polyphenylene sulfide
287:
228:Polyphenylene sulfide
35:
867:10.1246/bcsj.50.2564
854:Bull. Chem. Soc. Jpn
706:hydrodesulfurization
1476:not C, H or O)
1059:, pp. 555–559.
1035:, pp. 576–578.
750:John Wiley and Sons
662:thioether complexes
432:-adenosylmethionine
190:tetrahydrothiophene
176:. Because of their
1918:Hypervalent iodine
374:thiol-ene reaction
310:
188:, thiophene gives
38:
2059:Functional groups
2041:
2040:
1979:Sulfenyl chloride
1957:
1956:
1456:
1455:
1275:(only C, H and O)
1116:Functional groups
895:10.1021/cr500235v
889:(18): 8807–8864.
717:Grignard reagents
679:Sulfides undergo
568:Hydrogen peroxide
455:sulfur dichloride
436:methylating agent
367:Grignard reagents
335:Michael acceptors
296:, the amino acid
42:organic chemistry
16:(Redirected from
2066:
2008:
1913:Trifluoromethoxy
1481:
1480:
1477:
1280:
1279:
1276:
1129:
1109:
1102:
1095:
1086:
1085:
1081:
1060:
1054:
1048:
1042:
1036:
1030:
1024:
1018:
1012:
1006:
1000:
994:
988:
987:
967:
961:
960:
943:(9): 1540–1573.
932:
926:
925:
905:
899:
898:
883:Chemical Reviews
878:
872:
871:
869:
845:
839:
837:
790:978-3-64256765-0
770:
764:
763:
741:
723:adjacent to the
697:
656:
619:
584:
572:dimethyl sulfide
565:
553:
542:
495:
419:
402:produced from a
394:
385:+ H-SR' → R-CH
361:
343:
272:
271:
270:
262:
261:
253:
252:
244:
243:
69:
64:functional group
21:
2074:
2073:
2069:
2068:
2067:
2065:
2064:
2063:
2044:
2043:
2042:
2037:
2006:
1998:
1953:
1908:Trichloromethyl
1903:Trifluoromethyl
1877:
1854:
1816:
1793:
1688:
1657:Phosphine oxide
1609:
1475:
1473:
1472:
1470:
1468:
1466:
1464:
1462:
1452:
1412:
1355:
1274:
1273:
1268:
1263:
1253:
1127:
1126:
1118:
1113:
1064:
1063:
1055:
1051:
1043:
1039:
1031:
1027:
1019:
1015:
1007:
1003:
995:
991:
984:
968:
964:
933:
929:
906:
902:
879:
875:
846:
842:
833:...polysulfides
829:...polysulfanes
817:Cyclic sulfides
793:. p. 131:
791:
783:. p. 131.
771:
767:
760:
742:
738:
733:
695:
692:→ RH + R'H + H
691:
687:
654:
650:
646:
642:
638:
634:
630:
626:
622:
617:
613:
609:
605:
601:
597:
593:
589:
583:
579:
575:
563:
559:
551:
540:
536:
533:I → [S(CH
532:
528:
524:
520:
512:salts, such as
502:
493:
489:
485:
481:
477:
473:
469:
443:
427:. For example,
417:
392:
388:
384:
380:
359:
341:
315:
290:dimethylsulfide
269:
266:
265:
264:
260:
257:
256:
255:
251:
248:
247:
246:
242:
239:
238:
237:
235:
206:
199:
195:
167:
147:
133:
129:
125:
113:
109:
105:
100:dimethylsulfide
97:
93:
88:
67:
50:British English
28:
23:
22:
15:
12:
11:
5:
2072:
2062:
2061:
2056:
2039:
2038:
2036:
2035:
2034:
2033:
2028:
2016:
2009:
2003:
2000:
1999:
1997:
1996:
1994:Sulfinylamines
1991:
1986:
1981:
1976:
1974:Phosphoramides
1971:
1969:Isothiocyanate
1965:
1963:
1959:
1958:
1955:
1954:
1952:
1951:
1946:
1945:
1944:
1934:
1933:
1932:
1922:
1921:
1920:
1915:
1910:
1905:
1900:
1889:
1887:
1879:
1878:
1876:
1875:
1870:
1864:
1862:
1856:
1855:
1853:
1852:
1847:
1845:Selenenic acid
1842:
1840:Seleninic acid
1837:
1835:Selenonic acid
1832:
1826:
1824:
1818:
1817:
1815:
1814:
1809:
1803:
1801:
1795:
1794:
1792:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1715:
1714:
1704:
1698:
1696:
1690:
1689:
1687:
1686:
1681:
1676:
1671:
1670:
1669:
1659:
1654:
1649:
1644:
1643:
1642:
1632:
1631:
1630:
1628:Phosphodiester
1619:
1617:
1611:
1610:
1608:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1532:
1527:
1522:
1517:
1512:
1507:
1506:
1505:
1500:
1489:
1487:
1478:
1474:(one element,
1458:
1457:
1454:
1453:
1451:
1450:
1449:
1448:
1438:
1437:
1436:
1431:
1420:
1418:
1414:
1413:
1411:
1410:
1405:
1400:
1399:
1398:
1388:
1387:
1386:
1381:
1376:
1365:
1363:
1357:
1356:
1354:
1353:
1351:Methylenedioxy
1348:
1343:
1342:
1341:
1336:
1326:
1325:
1324:
1319:
1309:
1308:
1307:
1297:
1292:
1286:
1284:
1277:
1255:
1254:
1252:
1251:
1246:
1241:
1240:
1239:
1234:
1224:
1223:
1222:
1217:
1212:
1207:
1202:
1197:
1187:
1186:
1185:
1180:
1170:
1169:
1168:
1163:
1158:
1153:
1148:
1143:
1132:
1130:
1128:(only C and H)
1120:
1119:
1112:
1111:
1104:
1097:
1089:
1083:
1082:
1062:
1061:
1049:
1047:, p. 581.
1037:
1025:
1023:, p. 587.
1013:
1011:, p. 601.
1001:
999:, p. 596.
989:
982:
962:
927:
900:
873:
840:
789:
779:(1 ed.).
765:
758:
748:. Chichester:
735:
734:
732:
729:
699:
698:
693:
689:
681:hydrogenolysis
658:
657:
652:
648:
644:
640:
636:
632:
628:
624:
620:
615:
611:
607:
603:
599:
595:
591:
581:
577:
561:
544:
543:
538:
534:
530:
526:
522:
501:
498:
497:
496:
491:
487:
483:
479:
475:
471:
441:
438:in biological
421:
420:
404:photoinitiator
396:
395:
390:
386:
382:
363:
362:
345:
344:
314:
311:
300:, the vitamin
279:methanogenesis
267:
258:
249:
240:
205:
202:
197:
193:
166:
163:
146:
143:
131:
127:
123:
111:
107:
103:
95:
91:
87:
84:
80:periodic table
26:
9:
6:
4:
3:
2:
2071:
2060:
2057:
2055:
2052:
2051:
2049:
2032:
2029:
2027:
2024:
2023:
2022:
2021:
2017:
2015:
2014:
2010:
2005:
2004:
2001:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1966:
1964:
1960:
1950:
1947:
1943:
1940:
1939:
1938:
1935:
1931:
1928:
1927:
1926:
1923:
1919:
1916:
1914:
1911:
1909:
1906:
1904:
1901:
1899:
1896:
1895:
1894:
1891:
1890:
1888:
1886:
1885:
1880:
1874:
1873:Telluroketone
1871:
1869:
1866:
1865:
1863:
1861:
1857:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1827:
1825:
1823:
1819:
1813:
1810:
1808:
1805:
1804:
1802:
1800:
1796:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1759:Sulfonic acid
1757:
1755:
1752:
1750:
1749:Sulfinic acid
1747:
1745:
1744:Thiosulfonate
1742:
1740:
1737:
1735:
1734:Thiosulfinate
1732:
1730:
1729:Sulfenic acid
1727:
1725:
1722:
1720:
1717:
1713:
1710:
1709:
1708:
1705:
1703:
1700:
1699:
1697:
1695:
1691:
1685:
1684:Phosphaallene
1682:
1680:
1679:Phosphaalkyne
1677:
1675:
1674:Phosphaalkene
1672:
1668:
1665:
1664:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1641:
1638:
1637:
1636:
1633:
1629:
1626:
1625:
1624:
1621:
1620:
1618:
1616:
1612:
1606:
1603:
1601:
1598:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1541:
1538:
1536:
1533:
1531:
1528:
1526:
1523:
1521:
1518:
1516:
1513:
1511:
1508:
1504:
1501:
1499:
1496:
1495:
1494:
1491:
1490:
1488:
1486:
1482:
1479:
1459:
1447:
1444:
1443:
1442:
1439:
1435:
1432:
1430:
1427:
1426:
1425:
1422:
1421:
1419:
1415:
1409:
1406:
1404:
1401:
1397:
1394:
1393:
1392:
1389:
1385:
1382:
1380:
1377:
1375:
1372:
1371:
1370:
1367:
1366:
1364:
1362:
1358:
1352:
1349:
1347:
1346:Ethylenedioxy
1344:
1340:
1337:
1335:
1332:
1331:
1330:
1327:
1323:
1320:
1318:
1315:
1314:
1313:
1310:
1306:
1303:
1302:
1301:
1298:
1296:
1293:
1291:
1288:
1287:
1285:
1281:
1278:
1272:
1266:
1261:
1256:
1250:
1247:
1245:
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1046:
1041:
1034:
1029:
1022:
1017:
1010:
1005:
998:
993:
985:
983:0-7637-2425-4
979:
975:
974:
966:
958:
954:
950:
946:
942:
938:
931:
923:
919:
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904:
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868:
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844:
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786:
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778:
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769:
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759:0-471-95512-4
755:
751:
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736:
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686:
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621:
588:
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569:
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507:
468:
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407:
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400:free radicals
379:
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186:hydrogenation
183:
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83:
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54:
51:
47:
43:
34:
30:
19:
2018:
2011:
1925:Vinyl halide
1882:
1812:Borinic acid
1807:Boronic acid
1784:Thioxanthate
1124:Hydrocarbons
1069:
1052:
1040:
1028:
1016:
1004:
992:
972:
965:
940:
936:
930:
913:
909:
903:
886:
882:
876:
860:(10): 2564.
857:
853:
843:
832:
828:
825:Polysulfides
824:
821:heterocycles
820:
816:
812:
808:
804:
800:
796:
794:
775:
768:
745:
739:
710:
702:Raney nickel
700:
688:R-S-R' + 2 H
678:
659:
545:
503:
448:
429:
422:
408:
397:
371:
364:
346:
316:
207:
168:
159:
148:
138:
136:
98:S is called
89:
86:Nomenclature
61:organosulfur
56:
52:
45:
39:
29:
1989:Thiocyanate
1984:Sulfonamide
1949:Perchlorate
1937:Acyl halide
1898:Fluoroethyl
1779:Thionoester
1667:Phosphonium
1652:Phosphinate
1647:Phosphonous
1635:Phosphonate
1334:Hydroperoxy
1156:Cyclopropyl
838:(230 pages)
831:(formerly:
809:...sulfides
805:...sulfanyl
506:Lewis basic
463:mustard gas
444:2 reactions
425:alkyl group
313:Preparation
182:delocalized
116:thioanisole
2054:Thioethers
2048:Categories
1893:Haloalkane
1764:Thioketone
1719:Persulfide
1615:Phosphorus
1580:Isocyanate
1570:Isonitrile
1471:or oxygen
1469:hydrogen,
1465:not being
1446:Orthoester
1339:Dioxiranes
1317:Enol ether
1205:1-Propenyl
910:Org. Synth
801:...sulfane
731:References
670:phosphines
548:sulfoxides
434:acts as a
349:disulfides
331:aziridines
319:alkylation
298:methionine
294:coenzyme-M
232:Coenzyme M
213:methionine
210:amino acid
170:Thiophenes
165:Thiophenes
2026:inorganic
1860:Tellurium
1774:Thioester
1739:Sulfoxide
1724:Disulfide
1712:Sulfonium
1662:Phosphine
1640:Phosphite
1623:Phosphate
1555:Carbamate
1530:Hydrazone
1463:element,
1461:Only one
1434:Anhydride
1173:Methylene
797:thioether
552:R−S(=O)−R
510:sulfonium
500:Reactions
224:Petroleum
57:thioether
18:Thioether
2007:See also
1942:Chloride
1868:Tellurol
1822:Selenium
1789:Xanthate
1503:Ammonium
1485:Nitrogen
1467:carbon,
1424:Carboxyl
1391:Aldehyde
1379:Acryloyl
1361:carbonyl
1265:hydrogen
1220:Cumulene
1078:66-30401
957:20166107
606:→ OS(CH
556:sulfones
451:ethylene
327:epoxides
217:cofactor
215:and the
178:aromatic
72:volatile
53:sulphide
2031:organic
1830:Selenol
1754:Sulfone
1707:Sulfide
1605:NONOate
1600:Nitroso
1590:Nitrite
1585:Nitrate
1575:Cyanate
1565:Nitrile
1550:Amidine
1545:Imidate
1515:Nitrene
1510:Hydrazo
1498:Enamine
1429:Acetoxy
1417:carboxy
1384:Benzoyl
1322:Epoxide
1305:Methoxy
1295:Alcohol
1249:Carbene
1183:Methine
916:: 143.
813:...thio
721:protons
719:. The
711:Unlike
560:R−S(=O)
482:→ (ClC
381:R-CH=CH
275:methane
139:sulfane
120:anisole
46:sulfide
1930:Iodide
1850:Selone
1694:Sulfur
1403:Ketone
1396:Ketene
1374:Acetyl
1329:Peroxy
1300:Alkoxy
1290:Acetal
1271:oxygen
1260:carbon
1244:Alkyne
1237:Benzyl
1232:Phenyl
1215:Allene
1210:Crotyl
1190:Alkene
1178:Bridge
1166:Pentyl
1151:Propyl
1141:Methyl
1076:
980:
955:
787:
756:
725:sulfur
713:ethers
333:, and
323:thiols
302:biotin
220:biotin
68:R−S−R'
59:is an
1962:Other
1799:Boron
1769:Thial
1702:Thiol
1595:Nitro
1560:Imide
1540:Amide
1525:Oxime
1520:Imine
1493:Amine
1441:Ester
1408:Ynone
1312:Ether
1283:R-O-R
1258:Only
1200:Allyl
1195:Vinyl
1161:Butyl
1146:Ethyl
1136:Alkyl
623:OS(CH
474:+ 2 C
393:-S-R'
351:with
155:ether
76:ether
55:) or
1884:Halo
1369:Acyl
1269:and
1227:Aryl
1074:LCCN
978:ISBN
953:PMID
811:and
803:and
785:ISBN
754:ISBN
676:.
666:soft
651:+ H
643:S(CH
639:→ O
590:S(CH
576:S(CH
529:+ CH
521:S(CH
504:The
461:, a
44:, a
1535:Azo
945:doi
918:doi
891:doi
887:114
862:doi
631:+ H
614:+ H
598:+ H
585:):
566:).
470:SCl
389:-CH
321:of
245:SCH
192:, C
130:OCH
122:, C
110:SCH
40:In
2050::
1267:,
1262:,
951:.
941:49
939:.
914:58
912:.
885:.
858:50
856:.
852:.
835:).
752:.
708:.
564:−R
541:]I
516::
465::
446:.
406:.
376::
369:.
337:.
329:,
292:,
281:.
263:SO
254:CH
236:CH
234:,
222:.
151:pm
141:.
134:.
1108:e
1101:t
1094:v
1080:.
986:.
959:.
947::
924:.
920::
897:.
893::
870:.
864::
762:.
696:S
694:2
690:2
655:O
653:2
649:2
647:)
645:3
641:2
637:2
635:O
633:2
629:2
627:)
625:3
618:O
616:2
612:2
610:)
608:3
604:2
602:O
600:2
596:2
594:)
592:3
582:2
580:)
578:3
574:(
562:2
558:(
550:(
539:3
537:)
535:3
531:3
527:2
525:)
523:3
494:S
492:2
490:)
488:4
486:H
484:2
480:4
478:H
476:2
472:2
442:N
440:S
430:S
391:2
387:2
383:2
308:.
268:3
259:2
250:2
241:3
198:8
196:H
194:4
132:3
128:5
126:H
124:6
112:3
108:5
106:H
104:6
96:2
94:)
92:3
48:(
20:)
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