405:
1678:
1529:
1597:
1434:
345:
596:
compounds are less commonly encountered than organosodium compounds and are of limited utility. These compounds can be prepared by treatment of alkyl lithium compounds with the potassium, rubidium, and caesium alkoxides. Alternatively they arise from the organomercury compound, although this method
732:
Dietmar
Seyferth "Alkyl and Aryl Derivatives of the Alkali Metals: Strong Bases and Reactive Nucleophiles. 2. Wilhelm Schlenk's Organoalkali-Metal Chemistry. The Metal Displacement and the Transmetalation Reactions. Metalation of Weakly Acidic Hydrocarbons. Superbases" Organometallics 2009, volume
811:
William Clegg, Ben Conway, Alan R. Kennedy, Jan Klett, Robert E. Mulvey, Luca Russo "Synthesis and
Structures of sodium and -potassium with Bi- and Tridentate N-Donor Ligands" Eur. J. Inorg. Chem. 2011, pp. 721â726.
335:
Structural studies show however that sodium naphthalene has no Na-C bond, the sodium is invariably coordinated by ether or amine ligands. The related anthracene as well as lithium derivatives are well known.
376:
Simple organosodium compounds such as the alkyl and aryl derivatives are generally insoluble polymers. Because of its large radius, Na prefers a higher coordination number than does lithium in
928:
VrĂĄna, Jan; Jambor, Roman; RĹŻĹžiÄka, AleĹĄ; DostĂĄl, Libor (2018). "New
Synthetic Strategies Leading to [RNPNR]â Anions and the Isolation of the [P(Nt-Bu)3]3â Trianion".
669:
congested conformation. Several crystal structures of organopotassium compounds have been reported, establishing that they, like the sodium compounds, are polymeric.
1112:
965:
E. Weiss, "Structures of Organo Alkali Metal
Complexes and Related Compounds" Angewandte Chemie International Edition in English, 1993, volume 32, pages 1501â1523.
388:, the derivatives are more soluble. For example, TMEDA is soluble in hexane. Crystals have been shown to consist of chains of alternating Na(TMEDA) and CH
828:
Tarun K. Panda, Michael T. Gamer, and Peter W. Roesky "An
Improved Synthesis of Sodium and Potassium Cyclopentadienide" Organometallics 2003, 22, 877-878.
114:
CNa. One consequence of the highly polarized Na-C bond is that simple organosodium compounds often exist as polymers that are poorly soluble in solvents.
905:
Bock, Hans; Arad, Claudia; Näther, Christian; Havlas, Zdenek (1995). "The
Structures of Solvent-Separated Naphthalene and Anthracene Radical Anions".
773:. P. Schorigin, "Ăber die Natriumalkyl-Verbindungen und Ăźber die mit ihrer Hilfe ausgefĂźhrten Synthesen" Berichte, 1908, vol. 41, 2717.
1105:
1044:
Rolf
Ackermann, Ludwig Lange "Sodium Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim.
549:
Although organosodium chemistry has been described to be of "little industrial importance", it once was central to the production of
718:
749:
P. Schorigin, "Beiträge zur
Kenntnis der Kondensationen, welche durch Natrium bewirkt werden" Chem. Berichte 1907, vol. 40, 3111.
1810:
430:
304:
127:
In the original work the alkylsodium compound was accessed from the dialkylmercury compound by transmetallation. For example,
1098:
234:
789:. P. Schorigin, "Neue Synthese aromatischer Carbonsäuren aus den Kohlenwasserstoffen" Chem. Berichte 1908, vol. 41, 2723.
982:
SchĂźmann, Uwe; Behrens, Ulrich; Weiss, Erwin (April 1989). "Synthese und
Struktur von Bis, einem Phenylnatrium-Solvat".
605:(M = K, Rb, Cs) has six alkali metal centers bound to each methyl group. The methyl groups are pyramidal, as expected.
425:
Organosodium compounds are traditionally used as strong bases, although this application has been supplanted by other
1667:
1662:
1657:
1652:
1647:
1642:
1637:
1632:
1627:
1622:
1617:
1612:
1602:
1545:
1439:
1360:
1355:
1212:
436:
The higher alkali metals are known to metalate even some unactivated hydrocarbons and are known to self-metalate:
1703:
1405:
1375:
1365:
1345:
1333:
1301:
1266:
1234:
1202:
1197:
1157:
665:
is fast with lithium and sodium, but slow with the higher alkali metals. The higher alkali metals also favor the
1172:
1136:
1090:
67:
can also be classified as an organosodium compound since in the solid state sodium is bound to the aryl groups.
1748:
1743:
1738:
1733:
1728:
1723:
1718:
1713:
1708:
1693:
1683:
1534:
1509:
1504:
1489:
1474:
1454:
1449:
1400:
1328:
1311:
1261:
1256:
1251:
1246:
1222:
1182:
196:
64:
60:
38:
1698:
1688:
1499:
1484:
1469:
1459:
1444:
1385:
1370:
1350:
1340:
1321:
1316:
1306:
1296:
1239:
1207:
620:
384:
clusters. When the organic substituents are bulky and especially in the presence of chelating ligands like
107:
1177:
1167:
650:
Evidence for the formation of heavy alkali metal-organic intermediates is provided by the equilibration of
1607:
1522:
1464:
1427:
1422:
1410:
1390:
1380:
1286:
1281:
1276:
1217:
377:
308:
53:
1415:
1227:
1162:
1152:
781:. P. Schorigin, "Synthesen mittels Natrium und Halogenalkylen" Chem. Berichte, 1908, volume 41, 2711.
1494:
1479:
1291:
1271:
991:
195:
For some acidic organic compounds, the corresponding organosodium compounds arise by deprotonation.
52:. The application of organosodium compounds in chemistry is limited in part due to competition from
1395:
609:
558:
316:
238:
233:
Sodium acetylides form similarly. Often strong sodium bases are employed in place of the metal.
945:
878:
851:
714:
79:
71:
167:
The high solubility of lithium alkoxides in hexane is the basis of a useful synthetic route:
1074:
1045:
999:
966:
937:
910:
887:
829:
813:
790:
782:
774:
766:
750:
734:
666:
632:
518:
511:
404:
598:
200:
75:
364:("trityl sodium"), omitting all but the oxygen of the thf ligands. Selected distances: r
995:
17:
613:
554:
550:
476:
242:
128:
597:
is dated. The solid methyl derivatives adopt polymeric structures. Reminiscent of the
1804:
1767:
1016:
662:
49:
409:
846:
312:
794:
786:
778:
770:
678:
1049:
1003:
891:
765:
P. Schorigin, "Synthesen mittels
Natrium und Halogenalkylen" Ber. 41, 2711.
754:
1079:
1062:
103:
91:
34:
970:
949:
817:
380:. Methyl sodium adopts a polymeric structure consisting of interconnected
56:, which are commercially available and exhibit more convenient reactivity.
577:
The polymerization of butadiene and styrene is catalyzed by sodium metal.
914:
224:
95:
941:
628:
426:
99:
83:
833:
738:
1122:
876:
W. B. Renfrow Jr & C. R. Hauser (1939). "Triphenylmethylsodium".
651:
87:
46:
42:
1033:
The Merck index of chemicals and drugs: an encyclopedia for chemists
608:
A notable reagent that is based on a heavier alkali metal alkyl is
413:
403:
385:
344:
343:
401:
groups with NaâC distances ranging from 2.523(9) to 2.643(9) Ă
.
59:
The principal organosodium compound of commercial importance is
1094:
282:
Trityl sodium can be prepared by sodium-halogen exchange:
27:
Study of chemical compounds containing carbon-sodium bonds
698:
Synthesis of Organometallic Compounds: A Practical Guide
557:-like reaction is the basis of the industrial route to
70:
Organometal bonds in group 1 are characterised by high
106:
nature of organosodium compounds can be minimized by
78:
on carbon. This polarity results from the disparate
1759:
581:Organic derivatives of the heavier alkali metals
871:
869:
199:is thus prepared by treating sodium metal and
1106:
711:Organometallics : A Concise Introduction
319:, which is used as a soluble reducing agent:
8:
661:-but-2-ene catalysed by alkali metals. The
416:adduct, hydrogen atoms omitted for clarity.
1113:
1099:
1091:
728:
726:
713:(2nd Ed) (1992) from Wiley-VCH: Weinheim.
1125:with other elements in the periodic table
1078:
475:(1858) organosodium compounds react with
961:
959:
807:
805:
803:
690:
517:Some organosodium compounds degrade by
315:, it forms the deeply coloured radical
1142:
7:
1784:Academic research, no widespread use
1063:"Superbases for organic synthesis"
25:
1676:
1595:
1527:
1432:
1132:
631:to form the red-orange compound
305:polycyclic aromatic hydrocarbons
431:sodium bis(trimethylsilyl)amide
235:Sodium methylsulfinylmethylide
1:
82:of carbon (2.55) and that of
907:J. Chem. Soc., Chem. Commun.
847:"2,3-Diphenyl-1,3-Butadiene"
709:C. Elschenbroich, A. Salzer
514:undergo a similar reaction.
627:. This reagent reacts with
179:+ NaOâtâBu â LiOtâBu + NaCH
1827:
1061:Manfred Schlosser (1988).
861:, vol. 6, p. 531
845:Iwai, I.; Ide, J. (1988).
1673:
1592:
1144:
1140:
1130:
795:10.1002/cber.190804102210
787:10.1002/cber.190804102208
779:10.1002/cber.190804102209
771:10.1002/cber.190804102208
1050:10.1002/14356007.a24_341
1004:10.1002/ange.19891010420
892:10.15227/orgsyn.019.0083
755:10.1002/cber.19070400371
700:Sanshiro Komiya Ed. 1997
372:= 298 pm (avg of three).
303:Sodium also reacts with
237:is prepared by treating
197:Sodium cyclopentadienide
74:with corresponding high
65:Sodium tetraphenylborate
61:sodium cyclopentadienide
39:organometallic compounds
18:Organopotassium compound
1080:10.1351/pac198860111627
545:Industrial applications
378:organolithium compounds
123:Transmetallation routes
108:resonance stabilization
54:organolithium compounds
1811:Organosodium compounds
1779:Many uses in chemistry
1774:Core organic chemistry
971:10.1002/anie.199315013
818:10.1002/ejic.201000983
479:to give carboxylates:
417:
373:
309:one-electron reduction
278:Metal-halogen exchange
31:Organosodium chemistry
407:
347:
915:10.1039/C39950002393
311:. With solutions of
191:Deprotonation routes
996:1989AngCh.101..481S
930:Dalton Transactions
942:10.1039/C8DT02141D
559:triphenylphosphine
418:
374:
317:sodium naphthalene
133:Schorigin reaction
1798:
1797:
1754:
1753:
1073:(11): 1627â1634.
1035:, Paul G. Stecher
984:Angewandte Chemie
936:(25): 8434â8441.
909:(23): 2393â2394.
879:Organic Syntheses
859:Collected Volumes
852:Organic Syntheses
834:10.1021/om0207865
739:10.1021/om801047n
512:Grignard reagents
408:Structure of the
299:Electron transfer
137:Shorygin reaction
110:, for example, Ph
80:electronegativity
16:(Redirected from
1818:
1790:
1785:
1780:
1775:
1680:
1679:
1599:
1598:
1531:
1530:
1436:
1435:
1133:
1115:
1108:
1101:
1092:
1085:
1084:
1082:
1058:
1052:
1042:
1036:
1030:
1024:
1014:
1008:
1007:
979:
973:
963:
954:
953:
925:
919:
918:
902:
896:
894:
873:
864:
862:
855:
842:
836:
826:
820:
809:
798:
763:
757:
747:
741:
730:
721:
707:
701:
695:
633:benzyl potassium
610:Schlosser's base
519:beta-elimination
473:Wanklyn reaction
400:
399:
269:
268:
21:
1826:
1825:
1821:
1820:
1819:
1817:
1816:
1815:
1801:
1800:
1799:
1794:
1793:
1788:
1783:
1778:
1773:
1755:
1677:
1596:
1528:
1433:
1126:
1119:
1089:
1088:
1067:Pure Appl. Chem
1060:
1059:
1055:
1043:
1039:
1031:
1027:
1015:
1011:
981:
980:
976:
964:
957:
927:
926:
922:
904:
903:
899:
875:
874:
867:
857:
844:
843:
839:
827:
823:
810:
801:
764:
760:
748:
744:
731:
724:
708:
704:
696:
692:
687:
675:
646:
642:
638:
612:, a mixture of
604:
599:nickel arsenide
586:Organopotassium
583:
572:
568:
547:
540:
536:
532:
528:
506:
502:
498:
494:
490:
486:
467:
463:
459:
455:
451:
447:
443:
423:
398:
395:
394:
393:
391:
383:
371:
367:
363:
359:
355:
351:
348:Structure of (C
342:
330:
326:
301:
293:
290:CCl + 2 Na â Ph
289:
280:
273:
267:
264:
263:
262:
260:
256:
252:
228:
222:
218:
214:
210:
201:cyclopentadiene
193:
186:
182:
178:
174:
162:
158:
155:Hg + 2 Na â 2 C
154:
150:
146:
125:
120:
113:
76:nucleophilicity
28:
23:
22:
15:
12:
11:
5:
1824:
1822:
1814:
1813:
1803:
1802:
1796:
1795:
1792:
1791:
1786:
1781:
1776:
1771:
1768:Chemical bonds
1764:
1763:
1761:
1757:
1756:
1752:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1674:
1671:
1670:
1665:
1660:
1655:
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1610:
1605:
1600:
1593:
1590:
1589:
1585:
1584:
1581:
1578:
1575:
1572:
1569:
1566:
1563:
1560:
1557:
1554:
1551:
1548:
1543:
1540:
1537:
1532:
1525:
1520:
1516:
1515:
1512:
1507:
1502:
1497:
1492:
1487:
1482:
1477:
1472:
1467:
1462:
1457:
1452:
1447:
1442:
1437:
1430:
1425:
1419:
1418:
1413:
1408:
1403:
1398:
1393:
1388:
1383:
1378:
1373:
1368:
1363:
1358:
1353:
1348:
1343:
1338:
1336:
1331:
1325:
1324:
1319:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1274:
1269:
1264:
1259:
1254:
1249:
1244:
1242:
1237:
1231:
1230:
1225:
1220:
1215:
1210:
1205:
1200:
1195:
1189:
1188:
1185:
1180:
1175:
1170:
1165:
1160:
1155:
1149:
1148:
1145:
1143:
1141:
1139:
1131:
1128:
1127:
1120:
1118:
1117:
1110:
1103:
1095:
1087:
1086:
1053:
1037:
1025:
1009:
990:(4): 481â482.
974:
955:
920:
897:
865:
837:
821:
799:
758:
742:
722:
702:
689:
688:
686:
683:
682:
681:
674:
671:
644:
640:
636:
602:
601:structure, MCH
590:organorubidium
582:
579:
575:
574:
570:
566:
555:Wurtz coupling
551:tetraethyllead
546:
543:
542:
541:
538:
534:
530:
526:
509:
508:
504:
500:
496:
492:
488:
484:
477:carbon dioxide
469:
468:
465:
461:
457:
453:
449:
445:
441:
422:
419:
396:
389:
381:
369:
365:
361:
357:
353:
349:
341:
338:
333:
332:
328:
324:
300:
297:
296:
295:
291:
287:
279:
276:
275:
274:
271:
265:
258:
254:
250:
243:sodium hydride
231:
230:
226:
220:
216:
212:
208:
192:
189:
188:
187:
184:
180:
176:
172:
165:
164:
160:
156:
152:
148:
144:
129:diethylmercury
124:
121:
119:
116:
111:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1823:
1812:
1809:
1808:
1806:
1787:
1782:
1777:
1772:
1769:
1766:
1765:
1762:
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1710:
1707:
1705:
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1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1675:
1672:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1594:
1591:
1587:
1586:
1582:
1579:
1576:
1573:
1570:
1567:
1564:
1561:
1558:
1555:
1552:
1549:
1547:
1544:
1541:
1538:
1536:
1533:
1526:
1524:
1521:
1518:
1517:
1513:
1511:
1508:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1488:
1486:
1483:
1481:
1478:
1476:
1473:
1471:
1468:
1466:
1463:
1461:
1458:
1456:
1453:
1451:
1448:
1446:
1443:
1441:
1438:
1431:
1429:
1426:
1424:
1421:
1420:
1417:
1414:
1412:
1409:
1407:
1404:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1382:
1379:
1377:
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1357:
1354:
1352:
1349:
1347:
1344:
1342:
1339:
1337:
1335:
1332:
1330:
1327:
1326:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1253:
1250:
1248:
1245:
1243:
1241:
1238:
1236:
1233:
1232:
1229:
1226:
1224:
1221:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1190:
1186:
1184:
1181:
1179:
1176:
1174:
1171:
1169:
1166:
1164:
1161:
1159:
1156:
1154:
1151:
1150:
1146:
1138:
1135:
1134:
1129:
1124:
1121:Compounds of
1116:
1111:
1109:
1104:
1102:
1097:
1096:
1093:
1081:
1076:
1072:
1068:
1064:
1057:
1054:
1051:
1047:
1041:
1038:
1034:
1029:
1026:
1022:
1018:
1017:J. A. Wanklyn
1013:
1010:
1005:
1001:
997:
993:
989:
985:
978:
975:
972:
968:
962:
960:
956:
951:
947:
943:
939:
935:
931:
924:
921:
916:
912:
908:
901:
898:
893:
889:
885:
881:
880:
872:
870:
866:
860:
854:
853:
848:
841:
838:
835:
831:
825:
822:
819:
815:
808:
806:
804:
800:
796:
792:
788:
784:
780:
776:
772:
768:
762:
759:
756:
752:
746:
743:
740:
736:
733:28, pp 2â33.
729:
727:
723:
720:
719:3-527-28165-7
716:
712:
706:
703:
699:
694:
691:
684:
680:
677:
676:
672:
670:
668:
664:
663:isomerization
660:
656:
654:
648:
634:
630:
626:
624:
618:
617:-butyllithium
616:
611:
606:
600:
595:
594:organocaesium
591:
587:
580:
578:
569:+ 6 Na â PPh
564:
563:
562:
560:
556:
552:
544:
524:
523:
522:
520:
515:
513:
482:
481:
480:
478:
474:
439:
438:
437:
434:
432:
428:
420:
415:
411:
406:
402:
387:
379:
366:Na-C(central)
346:
339:
337:
322:
321:
320:
318:
314:
310:
306:
298:
285:
284:
283:
277:
248:
247:
246:
244:
240:
236:
229:
206:
205:
204:
202:
198:
190:
170:
169:
168:
142:
141:
140:
138:
134:
130:
122:
117:
115:
109:
105:
101:
97:
93:
89:
85:
81:
77:
73:
68:
66:
62:
57:
55:
51:
50:chemical bond
48:
44:
41:containing a
40:
36:
32:
19:
1789:Bond unknown
1192:
1070:
1066:
1056:
1040:
1032:
1028:
1023:, 125 (1858)
1020:
1012:
987:
983:
977:
933:
929:
923:
906:
900:
883:
877:
858:
850:
840:
824:
761:
745:
710:
705:
697:
693:
658:
652:
649:
622:
614:
607:
593:
589:
585:
584:
576:
565:3 PhCl + PCl
553:. A similar
548:
516:
510:
472:
470:
435:
424:
410:phenylsodium
375:
334:
302:
281:
232:
194:
166:
136:
132:
126:
69:
58:
30:
29:
313:naphthalene
294:C Na + NaCl
104:carbanionic
102:0.79). The
685:References
679:Alkynation
667:sterically
655:-but-2-ene
621:potassium
370:Na-C(ipso)
368:=256 pm, r
340:Structures
257:+ NaH â CH
1770:to carbon
625:-butoxide
533:â NaH + C
421:Reactions
331:+ Na â Na
207:2 Na+ 2 C
118:Synthesis
92:potassium
35:chemistry
1805:Category
950:29897357
673:See also
573:+ 6 NaCl
429:such as
427:reagents
360:CNa(thf)
215:â 2 Na C
96:rubidium
72:polarity
1588:
1019:, Ann.
992:Bibcode
629:toluene
491:Na + CO
471:In the
163:Na + Hg
131:in the
100:caesium
84:lithium
33:is the
1760:Legend
1123:carbon
948:
886:: 83.
717:
592:, and
270:Na + H
88:sodium
86:0.98,
47:sodium
43:carbon
659:trans
440:2 NaC
414:PMDTA
386:TMEDA
241:with
98:0.82
94:0.82
90:0.93
946:PMID
715:ISBN
657:and
635:(KCH
623:tert
619:and
448:â C
392:SiMe
307:via
261:SOCH
253:SOCH
239:DMSO
183:SiMe
175:SiMe
171:LiCH
1734:CEs
1729:CCf
1724:CBk
1719:CCm
1714:CAm
1709:CPu
1704:CNp
1694:CPa
1689:CTh
1668:CYb
1663:CTm
1658:CEr
1653:CHo
1648:CDy
1643:CTb
1638:CGd
1633:CEu
1628:CSm
1623:CPm
1618:CNd
1613:CPr
1608:CCe
1603:CLa
1583:Og
1580:Ts
1577:Lv
1574:Mc
1571:Fl
1568:Nh
1565:Cn
1562:Rg
1559:Ds
1556:Mt
1553:Hs
1550:Bh
1546:CSg
1542:Db
1539:Rf
1523:CRa
1519:Fr
1514:Rn
1510:CAt
1505:CPo
1500:CBi
1495:CPb
1490:CTl
1485:CHg
1480:CAu
1475:CPt
1470:CIr
1465:COs
1460:CRe
1450:CTa
1445:CHf
1440:CLu
1428:CBa
1423:CCs
1416:CXe
1406:CTe
1401:CSb
1396:CSn
1391:CIn
1386:CCd
1381:CAg
1376:CPd
1371:CRh
1366:CRu
1361:CTc
1356:CMo
1351:CNb
1346:CZr
1334:CSr
1329:CRb
1322:CKr
1317:CBr
1312:CSe
1307:CAs
1302:CGe
1297:CGa
1292:CZn
1287:CCu
1282:CNi
1277:CCo
1272:CFe
1267:CMn
1262:CCr
1252:CTi
1247:CSc
1240:CCa
1228:CAr
1223:CCl
1208:CSi
1203:CAl
1198:CMg
1193:CNa
1187:Ne
1158:CBe
1153:CLi
1147:He
1075:doi
1046:doi
1021:107
1000:doi
988:101
967:doi
938:doi
911:doi
888:doi
830:doi
814:doi
791:doi
783:doi
775:doi
767:doi
751:doi
735:doi
653:cis
647:).
525:NaC
495:â C
460:+ C
203::
135:or
45:to
37:of
1807::
1749:No
1744:Md
1739:Fm
1699:CU
1684:Ac
1535:Lr
1455:CW
1411:CI
1341:CY
1257:CV
1235:CK
1218:CS
1213:CP
1183:CF
1178:CO
1173:CN
1168:CC
1163:CB
1137:CH
1071:60
1069:.
1065:.
998:.
986:.
958:^
944:.
934:47
932:.
884:19
882:.
868:^
856:;
849:.
802:^
725:^
588:,
561::
521::
507:Na
503:CO
456:Na
433:.
325:10
286:Ph
249:CH
245::
223:+
143:(C
139::
63:.
1114:e
1107:t
1100:v
1083:.
1077::
1048::
1006:.
1002::
994::
969::
952:.
940::
917:.
913::
895:.
890::
863:.
832::
816::
797:.
793::
785::
777::
769::
753::
737::
645:5
643:H
641:6
639:C
637:2
615:n
603:3
571:3
567:3
539:4
537:H
535:2
531:5
529:H
527:2
505:2
501:5
499:H
497:2
493:2
489:5
487:H
485:2
483:C
466:6
464:H
462:2
458:2
454:4
452:H
450:2
446:5
444:H
442:2
412:-
397:3
390:2
382:4
362:3
358:3
356:)
354:5
352:H
350:6
329:8
327:H
323:C
292:3
288:3
272:2
266:2
259:3
255:3
251:3
227:2
225:H
221:5
219:H
217:5
213:6
211:H
209:5
185:3
181:2
177:3
173:2
161:5
159:H
157:2
153:2
151:)
149:5
147:H
145:2
112:3
20:)
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