31:
278:
owes its inertness to two factors: (i) it is symmetrical so that the negative charge is distributed equally over four atoms, and (ii) it is composed of highly electronegative fluorine atoms, which diminish the basicity of the anion. In addition to the weakly coordinating nature of the anion,
234:
is also conveniently the smallest weakly coordinating anion from the point of view of equivalent weight, often making it the anion of choice for preparing cationic reagents or catalysts for use in synthesis, in the absence of other substantial differences in chemical or physical factors.
374:, BARF, or ) must be employed. Moreover, in other cases of ostensibly "cationic" complexes, the fluorine atom in fact acts as a bridging ligand between boron and the cationic center. For instance, the gold complex was found crystallographically to contain two Au–F–B bridges.
851:
Cresswell, Alexander J.; Davies, Stephen G.; Roberts, Paul M.; Thomson, James E. (2015-01-28). "Beyond the Balz–Schiemann
Reaction: The Utility of Tetrafluoroborates and Boron Trifluoride as Nucleophilic Fluoride Sources".
815:
Cresswell, Alexander J.; Davies, Stephen G.; Roberts, Paul M.; Thomson, James E. (2015). "Beyond the Balz–Schiemann
Reaction: The Utility of Tetrafluoroborates and Boron Trifluoride as Nucleophilic Fluoride Sources".
377:
Transition and heavy metal fluoroborates are produced in the same manner as other fluoroborate salts; the respective metal salts are added to reacted boric and hydrofluoric acids.
1037:
765:
Abadie, Marc-Antoine; Trivelli, Xavier; Medina, Florian; Capet, Frédéric; Roussel, Pascal; Agbossou-Niedercorn, Francine; Michon, Christophe (2014-08-01).
1555:
672:
767:"Asymmetric Intramolecular Hydroamination of Alkenes in Mild and Wet Conditions—Structure and Reactivity of Cationic Binuclear Gold(I) Catalysts"
969:
1493:
1481:
1470:
1458:
1446:
1434:
1423:
1336:
1259:
1248:
1117:
696:
693:
salt is highly toxic). Most other transition metal tetrafluoroborates only exist as solvates of water, alcohols, ethers, or nitriles.
225:
does not suffer from these problems. Safety considerations, however, overshadow this inconvenience. With a formula weight of 86.8, BF
1110:
1859:
1030:
339:, both of which are even more stable toward hydrolysis and other chemical reactions and whose salts tend to be more lipophilic.
1305:
1136:
587:
1348:
425:
for the synthesis of aryl fluorides is the best known example of such a reaction. Ether and halopyridine adducts of HBF
422:
1854:
1217:
1143:
1095:
1023:
601:
1271:
1616:
1643:
1631:
1283:
1154:
1325:
1313:
1513:
1400:
1185:
1081:
766:
1651:
1392:
1572:
1537:
1505:
1225:
1177:
686:
1580:
1525:
1294:
1015:
952:
Willem L. Driessen, Jan
Reedijk (1992). "Solid Solvates: The Use of Weak Ligands in Coordination Chemistry".
895:
Guo, Rui; Qi, Xiaotian; Xiang, Hengye; Geaneotes, Paul; Wang, Ruihan; Liu, Peng; Wang, Yi-Ming (2020-06-02).
250:
anion is less nucleophilic and basic (and therefore more weakly coordinating) than nitrates, halides or even
1360:
342:
Extremely reactive cations such as those derived from Ti, Zr, Hf, and Si do in fact abstract fluoride from
741:
367:
185:
in the laboratory as a weakly coordinating anion. With organic compounds, especially amine derivatives,
142:
131:, which is used in similar ways in the laboratory. It arises by the reaction of fluoride salts with the
706:
An electrochemical cycle involving ferrous/ferric tetrafluoroborate is being used to replace thermal
76:
442:
312:
100:
266:, it is usually assume that the cation is the reactive agent and this tetrahedral anion is inert.
30:
797:
551:
92:
1002:
965:
934:
916:
897:"Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents"
877:
869:
833:
789:
430:
150:
135:
1062:
994:
957:
924:
908:
861:
825:
781:
746:
522:
514:
Fluoroborate is often used to isolate highly electrophilic cations. Some examples include:
17:
985:
Möller, H.; Lutz, H. D. (2010). "Crystal structure of thallium tetrafluoroborate, TlBF4".
715:
591:
929:
896:
729:
689:
and thallium tetrafluoroborate are convenient halide abstracting agents (although the
1848:
725:
595:
569:
518:
72:
801:
115:) and is valence isoelectronic with many stable and important species including the
711:
492:
394:
998:
1124:
721:
661:
614:
116:
961:
291:
salts are often more soluble in organic solvents (lipophilic) than the related
210:
146:
132:
1006:
920:
873:
793:
608:
536:
500:
938:
912:
881:
837:
785:
707:
690:
504:
251:
496:
421:
serves as a fluorine source to deliver an equivalent of fluoride. The
292:
865:
829:
409:
Despite the low reactivity of the tetrafluoroborate anion in general,
680:
664:, a fluorination agent, and other N–F electrophilic fluorine sources.
508:
390:
386:
296:
57:
29:
382:
1019:
378:
197:
forms potentially explosive derivatives. Disadvantages to
213:
and decomposition via loss of a fluoride ligand, whereas
987:
429:
have been reported to be effective reagents for the
495:and ammonium ions crystallize as water-soluble
441:Potassium fluoroborate is obtained by treating
157:As an anion in inorganic and organic chemistry
1031:
584:, the strongest commercial alkylating agents.
8:
732:, are often isolated as tetrafluoroborates.
667:Bromonium and iodonium species, including py
397:of these metals in a solution containing HBF
1038:
1024:
1016:
928:
901:Angewandte Chemie International Edition
757:
728:salts, ionic liquids and precursors to
445:with boric acid and hydrofluoric acid.
1071:
1046:Salts and covalent derivatives of the
1735:
7:
1058:
393:fluoroborates are prepared through
956:. Vol. 29. pp. 111–118.
697:Transition metal nitrile complexes
647:, and other cationic metallocenes.
209:include its slight sensitivity to
25:
366:is not an "innocent" anion and
145:with base, or by treatment of
71:. This tetrahedral species is
1:
999:10.1524/zkri.1992.201.3-4.285
327:, and hexafluoroantimonate,
254:. Thus, when using salts of
173:has led to decreased use of
18:Potassium tetrafluoroborate
1876:
1737:
962:10.1002/9780470132609.ch27
368:weakly coordinating anions
1073:
1055:
687:Silver tetrafluoroborate
1860:Non-coordinating anions
423:Balz–Schiemann reaction
913:10.1002/anie.202006278
786:10.1002/cctc.201402350
742:Non-coordinating anion
499:with the exception of
161:The popularization of
50:
143:tetrafluoroboric acid
34:The structure of the
33:
681:diaryliodonium salts
77:tetrafluoroberyllate
954:Inorganic Syntheses
907:(38): 16651–16660.
673:Barluenga's reagent
552:Diazonium compounds
443:potassium carbonate
405:As a fluoride donor
354:, so in such cases
313:hexafluorophosphate
101:tetrafluoroammonium
1855:Tetrafluoroborates
671:X (X = Br; X = I:
299:salts. Related to
93:tetrafluoromethane
51:
1842:
1841:
1836:
1835:
1128:
1048:tetrafluoroborate
971:978-0-470-13260-9
866:10.1021/cr5001805
830:10.1021/cr5001805
570:Meerwein reagents
525:), including H·(H
491:Fluoroborates of
437:Examples of salts
431:hydrofluorination
151:hydrofluoric acid
54:Tetrafluoroborate
36:tetrafluoroborate
16:(Redirected from
1867:
1126:
1059:
1040:
1033:
1026:
1017:
1011:
1010:
993:(3–4): 285–286.
982:
976:
975:
949:
943:
942:
932:
892:
886:
885:
854:Chemical Reviews
848:
842:
841:
818:Chemical Reviews
812:
806:
805:
780:(8): 2235–2239.
771:
762:
747:Fluoroboric acid
646:
645:
644:
636:
635:
627:
626:
583:
582:
581:
565:
564:
563:
523:fluoroboric acid
420:
419:
418:
365:
364:
363:
353:
352:
351:
338:
337:
336:
326:
325:
324:
310:
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265:
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249:
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196:
195:
194:
184:
183:
182:
172:
171:
170:
130:
129:
128:
114:
113:
112:
90:
89:
88:
70:
69:
68:
49:
48:
47:
21:
1875:
1874:
1870:
1869:
1868:
1866:
1865:
1864:
1845:
1844:
1843:
1838:
1837:
1659:
1655:
1647:
1639:
1635:
1624:
1620:
1588:
1584:
1576:
1563:
1559:
1545:
1541:
1533:
1529:
1521:
1517:
1509:
1501:
1497:
1489:
1485:
1480:
1478:
1474:
1466:
1462:
1454:
1450:
1442:
1438:
1433:
1431:
1427:
1408:
1404:
1396:
1368:
1364:
1356:
1352:
1344:
1340:
1335:
1333:
1329:
1321:
1317:
1309:
1304:
1302:
1298:
1293:
1291:
1287:
1279:
1275:
1267:
1263:
1258:
1256:
1252:
1233:
1229:
1221:
1193:
1189:
1181:
1162:
1158:
1153:
1151:
1147:
1142:
1140:
1132:
1123:
1121:
1116:
1114:
1109:
1107:
1103:
1099:
1085:
1066:
1051:
1044:
1014:
984:
983:
979:
972:
951:
950:
946:
894:
893:
889:
850:
849:
845:
814:
813:
809:
769:
764:
763:
759:
755:
738:
730:stable carbenes
716:Doe Run Company
702:
678:
670:
657:
653:
643:
640:
639:
638:
634:
631:
630:
629:
625:
622:
621:
620:
618:
605:
592:oxidizing agent
590:a one-electron
580:
577:
576:
575:
573:
562:
559:
558:
557:
555:
547:
542:
533:
528:
519:Solvated proton
487:
483:
479:
475:
471:
467:
460:
456:
452:
439:
428:
417:
414:
413:
412:
410:
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205:
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189:
188:
186:
181:
178:
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169:
166:
165:
164:
162:
159:
141:, treatment of
139:
127:
124:
123:
122:
120:
111:
108:
107:
106:
104:
98:
87:
84:
83:
82:
80:
67:
64:
63:
62:
60:
46:
43:
42:
41:
39:
28:
23:
22:
15:
12:
11:
5:
1873:
1871:
1863:
1862:
1857:
1847:
1846:
1840:
1839:
1834:
1833:
1830:
1827:
1824:
1821:
1818:
1815:
1812:
1809:
1806:
1803:
1800:
1797:
1794:
1791:
1787:
1786:
1783:
1780:
1777:
1774:
1771:
1768:
1765:
1762:
1759:
1756:
1753:
1750:
1747:
1744:
1740:
1739:
1736:
1733:
1732:
1729:
1726:
1723:
1720:
1717:
1714:
1711:
1708:
1705:
1702:
1699:
1696:
1693:
1690:
1687:
1684:
1681:
1678:
1674:
1673:
1670:
1667:
1664:
1661:
1657:
1653:
1649:
1645:
1641:
1637:
1633:
1629:
1626:
1622:
1618:
1614:
1611:
1608:
1605:
1602:
1599:
1596:
1593:
1590:
1586:
1582:
1578:
1574:
1569:
1568:
1565:
1561:
1557:
1553:
1550:
1547:
1543:
1539:
1535:
1531:
1527:
1523:
1519:
1515:
1511:
1507:
1503:
1499:
1495:
1491:
1487:
1483:
1476:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1444:
1440:
1436:
1429:
1425:
1421:
1418:
1415:
1412:
1410:
1406:
1402:
1398:
1394:
1389:
1388:
1385:
1382:
1379:
1376:
1373:
1370:
1366:
1362:
1358:
1354:
1350:
1346:
1342:
1338:
1331:
1327:
1323:
1319:
1315:
1311:
1307:
1300:
1296:
1289:
1285:
1281:
1277:
1273:
1269:
1265:
1261:
1254:
1250:
1246:
1243:
1240:
1237:
1235:
1231:
1227:
1223:
1219:
1214:
1213:
1210:
1207:
1204:
1201:
1198:
1195:
1191:
1187:
1183:
1179:
1174:
1173:
1170:
1167:
1164:
1160:
1156:
1149:
1145:
1138:
1134:
1130:
1119:
1112:
1105:
1101:
1097:
1093:
1090:
1087:
1083:
1078:
1077:
1074:
1072:
1070:
1068:
1064:
1057:
1056:
1053:
1052:
1045:
1043:
1042:
1035:
1028:
1020:
1013:
1012:
977:
970:
944:
887:
860:(2): 566–611.
843:
824:(2): 566–611.
807:
756:
754:
751:
750:
749:
744:
737:
734:
704:
703:
700:
694:
684:
676:
668:
665:
659:
655:
651:
648:
641:
632:
623:
612:
603:
599:
585:
578:
567:
560:
549:
545:
540:
531:
526:
489:
488:
485:
481:
477:
473:
469:
465:
462:
458:
454:
450:
438:
435:
426:
415:
406:
403:
398:
371:
360:
348:
333:
321:
305:
285:
272:
260:
244:
229:
219:
203:
191:
179:
167:
158:
155:
137:
125:
109:
96:
85:
65:
44:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1872:
1861:
1858:
1856:
1853:
1852:
1850:
1831:
1828:
1825:
1822:
1819:
1816:
1813:
1810:
1807:
1804:
1801:
1798:
1795:
1792:
1789:
1788:
1784:
1781:
1778:
1775:
1772:
1769:
1766:
1763:
1760:
1757:
1754:
1751:
1748:
1745:
1742:
1741:
1734:
1730:
1727:
1724:
1721:
1718:
1715:
1712:
1709:
1706:
1703:
1700:
1697:
1694:
1691:
1688:
1685:
1682:
1679:
1676:
1675:
1671:
1668:
1665:
1662:
1660:
1650:
1648:
1642:
1640:
1630:
1627:
1625:
1615:
1612:
1609:
1606:
1603:
1600:
1597:
1594:
1591:
1589:
1579:
1577:
1571:
1570:
1566:
1564:
1554:
1551:
1548:
1546:
1536:
1534:
1524:
1522:
1512:
1510:
1504:
1502:
1492:
1490:
1479:
1469:
1467:
1457:
1455:
1445:
1443:
1432:
1422:
1419:
1416:
1413:
1411:
1409:
1399:
1397:
1391:
1390:
1386:
1383:
1380:
1377:
1374:
1371:
1369:
1359:
1357:
1347:
1345:
1334:
1324:
1322:
1312:
1310:
1303:
1292:
1282:
1280:
1270:
1268:
1257:
1247:
1244:
1241:
1238:
1236:
1234:
1224:
1222:
1216:
1215:
1211:
1208:
1205:
1202:
1199:
1196:
1194:
1184:
1182:
1176:
1175:
1171:
1168:
1165:
1163:
1152:
1141:
1135:
1133:
1122:
1115:
1108:
1094:
1091:
1088:
1086:
1080:
1079:
1075:
1069:
1067:
1061:
1060:
1054:
1049:
1041:
1036:
1034:
1029:
1027:
1022:
1021:
1018:
1008:
1004:
1000:
996:
992:
988:
981:
978:
973:
967:
963:
959:
955:
948:
945:
940:
936:
931:
926:
922:
918:
914:
910:
906:
902:
898:
891:
888:
883:
879:
875:
871:
867:
863:
859:
855:
847:
844:
839:
835:
831:
827:
823:
819:
811:
808:
803:
799:
795:
791:
787:
783:
779:
775:
768:
761:
758:
752:
748:
745:
743:
740:
739:
735:
733:
731:
727:
726:formamidinium
723:
719:
717:
713:
709:
698:
695:
692:
688:
685:
682:
674:
666:
663:
660:
649:
616:
613:
610:
606:
600:
597:
596:nitrosylation
593:
589:
586:
571:
568:
553:
550:
548:
538:
534:
524:
520:
517:
516:
515:
512:
510:
506:
502:
498:
494:
493:alkali metals
463:
448:
447:
446:
444:
436:
434:
432:
424:
404:
402:
396:
392:
388:
384:
380:
375:
369:
340:
314:
298:
294:
253:
236:
212:
156:
154:
152:
148:
144:
140:
134:
118:
102:
94:
78:
74:
73:isoelectronic
59:
55:
37:
32:
19:
1047:
990:
986:
980:
953:
947:
904:
900:
890:
857:
853:
846:
821:
817:
810:
777:
773:
760:
720:
714:ores by the
712:lead sulfide
705:
544:
530:
521:(H (solv.),
513:
490:
453:+ 4 HF → HBF
440:
433:of alkynes.
408:
395:electrolysis
376:
341:
237:
160:
53:
52:
35:
774:ChemCatChem
722:Imidazolium
662:Selectfluor
615:Ferrocenium
117:perchlorate
1849:Categories
753:References
699:, e.g. BF
370:(e.g., SbF
211:hydrolysis
147:boric acid
133:Lewis acid
1007:2196-7105
921:1521-3773
874:0009-2665
794:1867-3899
609:nitration
539:"), H·(Et
537:hydronium
501:potassium
252:triflates
939:32485005
882:25084541
838:25084541
802:96851116
736:See also
708:smelting
691:thallium
675:) and Ar
611:reagent.
598:reagent.
572:such as
505:rubidium
497:hydrates
1738:
930:8287824
476:→ 2 KBF
293:nitrate
119:anion,
99:), and
56:is the
38:anion,
1295:FeO(BF
1005:
968:
937:
927:
919:
880:
872:
836:
800:
792:
509:cesium
507:, and
391:nickel
389:, and
387:copper
297:halide
1652:Pb(BF
1632:Hg(BF
1617:Pt(BF
1581:Ba(BF
1538:Sn(BF
1526:In(BF
1514:Cd(BF
1401:Sr(BF
1361:Zn(BF
1349:Cu(BF
1326:Ni(BF
1314:Co(BF
1284:Fe(BF
1272:Mn(BF
1226:Ca(BF
1186:Mg(BF
798:S2CID
770:(PDF)
464:2 HBF
457:+ 3 H
449:B(OH)
149:with
75:with
58:anion
27:Anion
1644:TlBF
1573:CsBF
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1790:**
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1746:La
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1716:Nh
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1710:Rg
1707:Ds
1704:Mt
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1698:Bh
1695:Sg
1692:Db
1689:Rf
1686:Lr
1683:**
1680:Ra
1677:Fr
1672:Rn
1669:At
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1663:Bi
1628:Au
1613:Ir
1610:Os
1607:Re
1601:Ta
1598:Hf
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1552:Te
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1494:(BF
1482:(BF
1471:(BF
1459:(BF
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1435:(BF
1424:(BF
1420:Nb
1417:Zr
1387:Kr
1384:Br
1381:Se
1378:As
1375:Ge
1372:Ga
1337:(BF
1260:(BF
1249:(BF
1242:Ti
1239:Sc
1218:KBF
1212:Ar
1209:Cl
1200:Si
1197:Al
1172:Ne
1129:)BF
1089:Be
1076:He
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995:doi
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958:doi
925:PMC
909:doi
862:doi
858:115
826:doi
822:115
782:doi
710:of
679:I (
650:(BF
574:OEt
556:ArN
511:.
480:+ H
468:+ K
379:Tin
329:SbF
295:or
215:ClO
187:ClO
175:ClO
121:ClO
95:(CF
91:),
81:BeF
1851::
1802:U
1743:*
1604:W
1592:*
1414:Y
1306:BF
1245:V
1206:S
1203:P
1169:F
1166:O
1159:BF
1155:NH
1148:BF
1144:NO
1118:BF
1111:BF
1104:BF
1092:B
1001:.
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964:.
933:.
923:.
915:.
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617:,
602:NO
588:NO
566:).
543:O)
535:("
529:O)
503:,
484:CO
472:CO
411:BF
401:.
385:,
381:,
356:BF
344:BF
317:PF
315:,
301:BF
281:BF
268:BF
256:BF
240:BF
199:BF
163:BF
153:.
136:BF
105:NF
61:BF
40:BF
1658:2
1656:)
1654:4
1646:4
1638:2
1636:)
1634:4
1623:2
1621:)
1619:4
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1562:4
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1532:3
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1520:2
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1516:4
1508:4
1500:2
1498:)
1496:4
1488:4
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1484:4
1477:3
1475:)
1473:4
1465:2
1463:)
1461:4
1453:4
1451:)
1449:4
1441:4
1439:)
1437:4
1430:4
1428:)
1426:4
1407:2
1405:)
1403:4
1395:4
1367:2
1365:)
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1301:2
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1192:2
1190:)
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1146:2
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1131:4
1125:(
1120:4
1113:4
1106:4
1102:7
1100:H
1098:7
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1084:4
1065:4
1039:e
1032:t
1025:v
1009:.
997::
974:.
960::
941:.
911::
884:.
864::
840:.
828::
804:.
784::
778:6
701:4
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677:2
669:2
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656:2
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652:4
642:2
637:)
633:5
628:H
624:5
604:2
579:3
561:2
554:(
546:n
541:2
532:n
527:2
486:3
482:2
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470:2
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461:O
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372:6
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349:4
334:6
322:6
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286:4
273:4
261:4
245:4
230:4
220:4
204:4
192:4
180:4
168:4
138:3
126:4
110:4
103:(
97:4
86:4
79:(
66:4
45:4
20:)
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