783:
1067:
Rivard, Eric; Merrill, W. Alexander; Fettinger, James C.; Wolf, Robert; Spikes, Geoffrey H.; Power, Philip P. (2007). "BoronâPnictogen
Multiple Bonds: Donor-Stabilized PB and AsB Bonds and a Hindered Iminoborane with a BâN Triple Bond".
1173:
Driess, M.; Rell, S.; Merz, K. (1999). "Ungewöhnliche
ReaktivitÀt der Silicium-Phosphor-Doppelbindung in einem Silyliden(fluorsilyl)phosphan: Intramolekulare C,H-Inserierung und seine Umwandlung in ein neues Silyliden(silyl)phosphan".
1201:
Suzuki, Hiroyuki; Tokitoh, Norihiro; Nagase, Shigeru; Okazaki, Renji (1994). "The First
Genuine Silicon-Sulfur Double-Bond Compound: Synthesis and Crystal Structure of a Kinetically Stabilized Silanethione".
972:
Vidovic, Dragoslav; Moore, Jennifer A.; Jones, Jamie N.; Cowley, Alan H. (2005). "Synthesis and
Characterization of a Coordinated Oxoborane: Lewis Acid Stabilization of a BoronâOxygen Double Bond".
71:=2 are much stronger than usual, because lone pair repulsion weakens their sigma bonding but not their pi bonding.) An example is the rapid polymerization that occurs upon condensation of
795:
1103:
Tokitoh, Norihiro; Ito, Mitsuhiro; Okazaki, Renji (1996). "Formation and reactions of a thioxoborane, a novel boron-sulfur double-bond compound".
1187:
1130:
Zigler, Steven S.; West, Robert; Michl, Josef (1986). "Observation of a
Silanimine in an Inert Matrix and in Solution at Low Temperature".
63:>2 orbitals of the two atoms. Although such compounds are not intrinsically unstable, they instead tend to dimerize or even
1229:
Allwohn, JĂŒrgen; Pilz, Monika; Hunold, Ralf; Massa, Werner; Berndt, Armin (1990). "Compounds with a BoronâCarbon Triple Bond".
1062:
937:
Rosas-Garcia, Victor M.; Crawford, T. Daniel (2003). "The aminoboranylideneâiminoborane isomerization".
814:
attached to an atom adjacent to a double bond. In bromoalkenes, the CâBr bond is very stable, but in an
1292:
397:
1421:
32:
1256:
Kuprat, Marcus; Schulz, Axel (2013). "Arsa-Diazonium Salts With an
ArsenicâNitrogen Triple Bond".
652:
1007:
Franz, Daniel; Szilvåsi, Tibor; Pöthig, Alexander; Inoue, Shigeyoshi (2019). "Isolation of an
761:
1389:
1319:
946:
818:
bromide, this bond is very reactive. Likewise, bromobenzenes are generally inert, whereas
8:
1345:
Schmidt, Otto (1932). "Ăber den Ort der
Sprengung von CâC-Bindungen in KettenmolekĂŒlen".
791:
401:
1393:
1323:
950:
55:). Double bonds for these heavier elements, when they exist, are often weak due to poor
1362:
1036:
621:
914:
1273:
1116:
1085:
1040:
1028:
989:
810:
Another unrelated double bond rule exists that relates to the enhanced reactivity of
1366:
1397:
1354:
1327:
1265:
1238:
1211:
1183:
1139:
1112:
1077:
1020:
981:
954:
910:
883:
856:
673:
194:
44:
40:
28:
605:
309:
56:
371:
352:
294:
1188:
10.1002/(SICI)1521-3749(199907)625:7<1119::AID-ZAAC1119>3.0.CO;2-1
1415:
928:
874:
Kutzelnigg, Werner (1984). "Chemical
Bonding in Higher Main Group Elements".
616:
611:
417:
393:
328:
246:
1358:
1277:
1269:
1242:
1089:
1032:
1024:
993:
887:
860:
827:
702:
387:
263:
1143:
823:
811:
580:
317:
313:
282:
276:
52:
48:
1215:
1165:
641:
629:
569:
505:
251:
160:
64:
1401:
1331:
1081:
985:
958:
747:
661:
645:
531:
336:
322:
299:
202:
20:
1380:
Hoogenboom, Bernard E. (1998). "A History of the Double-Bond Rule".
1310:
Hoogenboom, Bernard E. (1998). "A History of the Double-Bond Rule".
819:
688:
560:
466:
413:
365:
340:
332:
303:
236:
189:
121:
72:
901:
West, Robert (2002). "Multiple bonds to silicon: 20 years later".
273:
silanimines, rare, easy oligomerization, observed only at low temp
1058:
600:
544:
492:
344:
268:
241:
147:
822:
bromides are reactive. The first to observe the phenomenon was
595:
518:
479:
453:
226:
173:
134:
108:
815:
440:
231:
95:
16:
Chemistry rule: elements of period â„ 3 only form single bonds
1200:
1066:
1006:
847:
Jutzi, Peter (1975). "New
ElementâCarbon (pâp)Ï Bonds".
213:
boranylidenephosphanes, rare, stable compounds are known
971:
1228:
1160:
BuSi=PAr*, where Ar* is 2,4,6-trisiopropylphenyl and
67:. (Moreover, the multiple bonds of the elements with
936:
302:, Si=O bonds extremely reactive, oligomerization to
1176:Zeitschrift fĂŒr Anorganische und Allgemeine Chemie
849:Angewandte Chemie International Edition in English
47:and higher) tend not to form multiple bonds (e.g.
1102:
1413:
1011:âHeterocyclic Carbene Complex of a Borasilene".
1129:
431:Triple bonds for carbon and nearest neighbours
86:Double bonds for carbon and nearest neighbours
1172:
826:in 1885. The name for the rule was coined by
1255:
790:It has been suggested that this section be
82:. Numerous exceptions to the rule exist.
1379:
1309:
873:
377:silanethiones, rare, easy oligomerization
1204:Journal of the American Chemical Society
974:Journal of the American Chemical Society
1344:
876:Angewandte Chemie International Edition
1414:
1290:
1291:Ritter, Stephen K. (March 21, 2005).
846:
396:and phosphine sulfides, for example,
1347:Zeitschrift fĂŒr Physikalische Chemie
900:
776:
13:
1293:"Sulfur's Turn for Multiple Bonds"
1194:
1150:
935:to triple-bonded iminoborane HBNH
14:
1433:
1123:
1096:
1047:
1000:
965:
921:
772:
781:
565:Borataalkynes have been observed
1373:
1338:
1303:
1297:Chemical & Engineering News
1284:
1249:
1222:
939:The Journal of Chemical Physics
927:Some research has been done on
429:
425:
84:
1013:Chemistry â A European Journal
894:
867:
840:
676:has some triple-bond character
339:(R-S(=O)-RâČ, compounds with a
1:
1382:Journal of Chemical Education
1312:Journal of Chemical Education
1063:2,2,6,6-tetramethylpiperidine
915:10.1016/S0277-5387(01)01017-8
833:
1117:10.1016/0040-4039(96)01039-8
794:out into another article. (
370:silylidenephosphanes a.k.a.
7:
39:) greater than 2 for their
10:
1438:
1258:Angew. Chem. Int. Ed. Engl
1231:Angew. Chem. Int. Ed. Engl
398:triphenylphosphine sulfide
766:
758:
744:
737:
713:
706:
699:
692:
685:
678:
670:
657:
649:
638:
585:
541:
528:
515:
502:
489:
410:
392:common compounds such as
384:
362:
291:
260:
170:
157:
144:
199:aminoboranylidenes, rare
75:, the heavy analogue of
33:principal quantum number
1359:10.1515/zpch-1932-15931
1270:10.1002/anie.201302725
1243:10.1002/anie.199010321
1025:10.1002/chem.201902877
888:10.1002/anie.198402721
861:10.1002/anie.197502321
653:Phosphorus mononitride
1057:, where Ar* is 2,6-di
762:Arsenic monophosphide
207:rapid oligomerization
1144:10.1246/cl.1986.1025
1053:Example: Ar*P=B(TMP)
402:dithiadiphosphetanes
216:thioxoboranes, rare
1394:1998JChEd..75..596H
1324:1998JChEd..75..596H
1216:10.1021/ja00104a052
1210:(25): 11578â11579.
1105:Tetrahedron Letters
1070:Inorganic Chemistry
1061:-phenyl and TMP is
1019:(47): 11036â11041.
951:2003JChPh.11910647R
945:(20): 10647â10652.
432:
87:
622:Carbon monosulfide
430:
210:borasilenes (rare)
85:
1402:10.1021/ed075p596
1332:10.1021/ed075p596
1264:(28): 7126â7130.
1132:Chemistry Letters
1111:(29): 5145â5148.
1082:10.1021/ic062076n
986:10.1021/ja0507564
980:(13): 4566â4567.
959:10.1063/1.1620498
808:
807:
803:
770:
769:
423:
422:
269:nitroso compounds
195:alkylideneboranes
45:period 3 elements
41:valence electrons
1429:
1422:Chemical bonding
1406:
1405:
1377:
1371:
1370:
1342:
1336:
1335:
1307:
1301:
1300:
1288:
1282:
1281:
1253:
1247:
1246:
1237:(9): 1032â1033.
1226:
1220:
1219:
1198:
1192:
1191:
1182:(7): 1119â1123.
1154:
1148:
1147:
1138:(6): 1025â1028.
1127:
1121:
1120:
1100:
1094:
1093:
1076:(8): 2971â2978.
1051:
1045:
1044:
1004:
998:
997:
969:
963:
962:
925:
919:
918:
909:(5â6): 467â472.
898:
892:
891:
871:
865:
864:
844:
799:
785:
784:
777:
735:
734:
733:
730:
674:Silicon monoxide
433:
310:phosphine oxides
88:
81:
25:double bond rule
1437:
1436:
1432:
1431:
1430:
1428:
1427:
1426:
1412:
1411:
1410:
1409:
1378:
1374:
1343:
1339:
1308:
1304:
1289:
1285:
1254:
1250:
1227:
1223:
1199:
1195:
1155:
1151:
1128:
1124:
1101:
1097:
1056:
1052:
1048:
1005:
1001:
970:
966:
934:
926:
922:
899:
895:
872:
868:
845:
841:
836:
804:
786:
782:
775:
731:
728:
727:
725:
721:
717:
606:Carbon monoxide
547:
543:
534:
530:
521:
517:
508:
504:
495:
491:
482:
478:
469:
465:
456:
452:
443:
439:
428:
350:
327:numerous, e.g.
321:
308:numerous, e.g.
206:
176:
172:
163:
159:
150:
146:
137:
133:
124:
120:
111:
107:
98:
94:
80:
76:
57:orbital overlap
17:
12:
11:
5:
1435:
1425:
1424:
1408:
1407:
1372:
1337:
1302:
1283:
1248:
1221:
1193:
1149:
1122:
1095:
1054:
1046:
999:
964:
932:
920:
893:
882:(4): 272â295.
866:
855:(4): 232â245.
838:
837:
835:
832:
806:
805:
789:
787:
780:
774:
773:Other meanings
771:
768:
767:
765:
759:
757:
753:
752:
750:
745:
743:
739:
738:
736:
723:
719:
714:
712:
708:
707:
705:
700:
698:
694:
693:
691:
686:
684:
680:
679:
677:
671:
669:
665:
664:
658:
656:
650:
648:
639:
637:
633:
632:
627:
625:
619:
617:phosphaalkynes
614:
609:
603:
598:
593:
591:
587:
586:
584:
566:
563:
558:
554:
553:
540:
527:
514:
501:
488:
475:
462:
449:
436:
427:
424:
421:
420:
418:thiosulfoxides
411:
409:
405:
404:
394:thiophosphates
390:
385:
383:
379:
378:
375:
372:phosphasilenes
368:
363:
361:
357:
356:
353:sulfonyl group
348:
325:
306:
297:
295:Singlet oxygen
292:
290:
286:
285:
280:
274:
271:
266:
261:
259:
255:
254:
249:
247:phosphaalkenes
244:
239:
234:
229:
224:
222:
218:
217:
214:
211:
208:
200:
197:
192:
187:
183:
182:
169:
156:
143:
130:
117:
104:
91:
78:
15:
9:
6:
4:
3:
2:
1434:
1423:
1420:
1419:
1417:
1403:
1399:
1395:
1391:
1387:
1383:
1376:
1368:
1364:
1360:
1356:
1352:
1348:
1341:
1333:
1329:
1325:
1321:
1317:
1313:
1306:
1298:
1294:
1287:
1279:
1275:
1271:
1267:
1263:
1259:
1252:
1244:
1240:
1236:
1232:
1225:
1217:
1213:
1209:
1205:
1197:
1189:
1185:
1181:
1177:
1170:
1168:
1163:
1159:
1153:
1145:
1141:
1137:
1133:
1126:
1118:
1114:
1110:
1106:
1099:
1091:
1087:
1083:
1079:
1075:
1071:
1064:
1060:
1050:
1042:
1038:
1034:
1030:
1026:
1022:
1018:
1014:
1010:
1003:
995:
991:
987:
983:
979:
975:
968:
960:
956:
952:
948:
944:
940:
930:
929:isomerization
924:
916:
912:
908:
904:
897:
889:
885:
881:
877:
870:
862:
858:
854:
850:
843:
839:
831:
829:
825:
821:
817:
813:
802:
801:(August 2023)
797:
793:
788:
779:
778:
763:
760:
755:
754:
751:
749:
746:
741:
740:
715:
710:
709:
704:
701:
696:
695:
690:
687:
682:
681:
675:
672:
667:
666:
663:
659:
654:
651:
647:
643:
640:
635:
634:
631:
628:
626:
623:
620:
618:
615:
613:
610:
607:
604:
602:
599:
597:
594:
592:
589:
588:
582:
578:
574:
572:
568:Observed in (
567:
564:
562:
559:
556:
555:
551:
546:
538:
533:
525:
520:
512:
507:
499:
494:
486:
481:
476:
473:
468:
463:
460:
455:
450:
447:
442:
437:
435:
434:
419:
415:
412:
407:
406:
403:
399:
395:
391:
389:
386:
381:
380:
376:
373:
369:
367:
364:
359:
358:
354:
346:
342:
338:
334:
330:
329:sulfuric acid
326:
324:
319:
315:
311:
307:
305:
301:
298:
296:
293:
288:
287:
284:
281:
278:
275:
272:
270:
267:
265:
264:azo compounds
262:
257:
256:
253:
250:
248:
245:
243:
240:
238:
235:
233:
230:
228:
225:
223:
220:
219:
215:
212:
209:
204:
201:
198:
196:
193:
191:
188:
185:
184:
180:
175:
167:
162:
154:
149:
141:
136:
131:
128:
123:
118:
115:
110:
105:
102:
97:
92:
90:
89:
83:
74:
70:
66:
62:
58:
54:
50:
46:
42:
38:
34:
30:
26:
22:
1385:
1381:
1375:
1350:
1346:
1340:
1315:
1311:
1305:
1296:
1286:
1261:
1257:
1251:
1234:
1230:
1224:
1207:
1203:
1196:
1179:
1175:
1166:
1161:
1157:
1156:Example: Ar*
1152:
1135:
1131:
1125:
1108:
1104:
1098:
1073:
1069:
1049:
1016:
1012:
1008:
1002:
977:
973:
967:
942:
938:
923:
906:
902:
896:
879:
875:
869:
852:
848:
842:
828:Otto Schmidt
809:
800:
716:Observed in
703:Diphosphorus
576:
570:
549:
536:
523:
510:
497:
484:
471:
458:
445:
426:Triple bonds
400:and certain
388:diphosphenes
343:group), and
318:phosphinates
314:phosphonates
283:sulfilimines
178:
165:
152:
139:
126:
113:
100:
68:
60:
59:between the
53:triple bonds
49:double bonds
36:
27:states that
24:
18:
1353:: 337â356.
824:Conrad Laar
812:sigma bonds
630:arsaalkynes
581:iminoborane
277:phosphazene
252:thioketones
1388:(5): 596.
1318:(5): 596.
903:Polyhedron
834:References
642:Dinitrogen
506:phosphorus
337:sulfoxides
323:phosphates
203:oxoboranes
161:phosphorus
65:polymerize
1041:195660396
830:in 1932.
748:Digermyne
689:disilynes
662:diazonium
646:Diazonium
579:-Bu) (an
561:diborynes
532:germanium
366:disilenes
351:-RâČ, the
304:siloxanes
300:silanones
237:carbonyls
190:diborenes
21:chemistry
1416:Category
1367:99620074
1278:23740867
1090:17338516
1033:31241215
994:15796509
820:benzylic
601:cyanides
467:nitrogen
414:disulfur
347:(R-S(=O)
345:sulfones
341:sulfinyl
333:sulfates
205:, rare,
122:nitrogen
73:disulfur
29:elements
1390:Bibcode
1320:Bibcode
1059:mesityl
947:Bibcode
931:of B=NH
796:Discuss
612:silynes
596:alkynes
545:arsenic
493:silicon
242:silenes
227:alkenes
148:silicon
31:with a
1365:
1276:
1171:; see
1169:-butyl
1164:Bu is
1088:
1065:; see
1039:
1031:
992:
764:(AsâĄP)
519:sulfur
480:oxygen
454:carbon
374:, rare
232:imines
174:sulfur
135:oxygen
109:carbon
23:, the
1363:S2CID
1037:S2CID
816:allyl
792:split
660:Arsa-
655:(PâĄN)
624:(CâĄS)
608:(CâĄO)
441:boron
279:(P=N)
96:boron
1351:159A
1274:PMID
1167:tert
1086:PMID
1029:PMID
990:PMID
575:)BN(
552:=4)
181:=3)
51:and
1398:doi
1355:doi
1328:doi
1266:doi
1239:doi
1212:doi
1208:116
1184:doi
1180:625
1140:doi
1113:doi
1078:doi
1021:doi
982:doi
978:127
955:doi
943:119
911:doi
884:doi
857:doi
756:As
742:Ge
683:Si
573:-Bu
539:=4)
526:=3)
513:=3)
500:=3)
487:=2)
474:=2)
461:=2)
448:=2)
360:Si
168:=3)
155:=3)
142:=2)
129:=2)
116:=2)
103:=2)
19:In
1418::
1396:.
1386:75
1384:.
1361:.
1349:.
1326:.
1316:75
1314:.
1295:.
1272:.
1262:52
1260:.
1235:29
1233:.
1206:.
1178:.
1136:15
1134:.
1109:37
1107:.
1084:.
1074:46
1072:.
1035:.
1027:.
1017:25
1015:.
988:.
976:.
953:.
941:.
907:21
905:.
880:23
878:.
853:14
851:.
798:)
729:2+
718:(I
711:S
697:P
668:O
644:,
636:N
590:C
557:B
542:As
529:Ge
490:Si
416:,
408:S
382:P
355:)
335:,
331:,
316:,
312:,
289:O
258:N
221:C
186:B
145:Si
1404:.
1400::
1392::
1369:.
1357::
1334:.
1330::
1322::
1299:.
1280:.
1268::
1245:.
1241::
1218:.
1214::
1190:.
1186::
1162:t
1158:t
1146:.
1142::
1119:.
1115::
1092:.
1080::
1055:2
1043:.
1023::
1009:N
996:.
984::
961:.
957::
949::
933:2
917:.
913::
890:.
886::
863:.
859::
732:2
726:S
724:2
722:)
720:2
583:)
577:t
571:t
550:n
548:(
537:n
535:(
524:n
522:(
516:S
511:n
509:(
503:P
498:n
496:(
485:n
483:(
477:O
472:n
470:(
464:N
459:n
457:(
451:C
446:n
444:(
438:B
349:2
320:,
179:n
177:(
171:S
166:n
164:(
158:P
153:n
151:(
140:n
138:(
132:O
127:n
125:(
119:N
114:n
112:(
106:C
101:n
99:(
93:B
79:2
77:O
69:n
61:n
43:(
37:n
35:(
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