129:
187:
241:
229:
1474:
147:
111:
165:
253:
1468:
402:
a whole is not planar. In diplumbenes the Pb=Pb bond length can be longer than that of many corresponding single bonds
Plumbenes and stannenes generally dissociate in solution into monomers with bond enthalpies that are just a fraction of the corresponding single bonds. Some double bonds plumbenes and stannenes are similar in strength to hydrogen bonds. The
1480:
401:
CHSn: (stannanediyl, a carbene analog). The bonding comprises two weak donor acceptor bonds, the lone pair on each tin atom overlapping with the empty p orbital on the other. In contrast, in disilenes each silicon atom has planar coordination but the substituents are twisted so that the molecule as
377:
elements. Unlike the alkenes these compounds are not planar but adopt twisted and/or trans bent structures. These effects become more pronounced for the heavier elements. The distannene (Me
210:. The three sp orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane. When the carbon atoms approach each other, two of the sp orbitals overlap to form a
393:
has a tin-tin bond length just a little shorter than a single bond, a trans bent structure with pyramidal coordination at each tin atom, and readily dissociates in solution to form (Me
987:
1567:
842:
732:
846:
736:
240:
228:
218:. For maximum overlap, the p-orbitals have to remain parallel, and, therefore, rotation around the central bond is not possible. This property gives rise to
312:
1685:
1612:
1293:
403:
128:
1225:
980:
807:
761:
97:
is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in
303:
In molecules with alternating double bonds and single bonds, p-orbital overlap can exist over multiple atoms in a chain, giving rise to a
1018:
697:
146:
1547:
1532:
973:
288:
versus 368 kJ mol but not twice as much as the pi-bond is weaker than the sigma bond due to less effective pi-overlap.
1356:
1383:
1344:
1334:
164:
110:
1339:
1256:
821:
775:
1286:
865:
Power, Philip P. (1999). "π-Bonding and the Lone Pair Effect in
Multiple Bonds between Heavier Main Group Elements".
711:
908:
350:
1607:
1602:
1711:
1592:
1582:
1557:
1527:
1246:
1230:
98:
1373:
1205:
1634:
1537:
1509:
1279:
252:
903:
Wang, Yuzhong; Robinson, Gregory H. (2009). "Unique homonuclear multiple bonding in main group compounds".
270:
186:
74:, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the
1678:
1639:
1165:
1160:
203:
195:
1673:
1597:
1488:
1351:
1310:
1131:
1499:
1363:
1329:
1251:
1145:
291:
In an alternative representation, the double bond results from two overlapping sp orbitals as in a
219:
214:. At the same time, the two p-orbitals approach (again in the same plane) and together they form a
1663:
1418:
836:
726:
152:
83:
43:
664:
638:
1649:
1438:
1398:
1388:
1220:
1013:
954:
920:
882:
813:
803:
767:
757:
703:
693:
612:
304:
1690:
1473:
1430:
1403:
946:
912:
874:
346:
331:
71:
937:
Pyykkö, Pekka; Riedel, Sebastian; Patzschke, Michael (2005). "Triple-Bond
Covalent Radii".
1542:
1413:
1170:
316:
1668:
1577:
1378:
1113:
1097:
1092:
1008:
207:
58:
group between a carbon atom and an oxygen atom. Other common double bonds are found in
1705:
1626:
1586:
1519:
1448:
1321:
1302:
1186:
1126:
1121:
1102:
996:
512:
508:
472:
222:. Double bonds are shorter than single bonds because p-orbital overlap is maximized.
90:
35:
1572:
534:
374:
59:
1658:
1408:
1087:
1077:
320:
285:
273:
75:
47:
1467:
246:
Two p-orbitals overlap to form a pi-bond in a plane parallel to the sigma plane
1069:
1053:
1043:
463:
211:
94:
27:
Chemical bond involving four bonding electrons; has one sigma plus one pi bond
817:
771:
1393:
1368:
1191:
707:
500:
292:
234:
2 sp orbitals (total of 3 such orbitals) approach to form a sp-sp sigma bond
67:
54:. Many double bonds exist between two different elements: for example, in a
50:. Double bonds occur most commonly between two carbon atoms, for example in
958:
950:
924:
886:
17:
965:
797:
751:
1058:
687:
560:
453:
338:
324:
262:
199:
116:
55:
1048:
586:
504:
495:
258:
215:
170:
134:
78:
is used for this. Double bonds were introduced in chemical notation by
878:
689:
Advanced organic chemistry : reactions, mechanisms, and structure
916:
490:
448:
362:
342:
334:
277:
79:
51:
1479:
802:. Sundberg, Richard J., 1938- (5th ed.). New York: Springer.
467:
458:
308:
281:
185:
63:
1271:
39:
1275:
969:
280:
with 154 pm. The double bond is also stronger, 636
89:
Double bonds involving carbon are stronger and shorter than
898:
896:
1648:
1625:
1556:
1518:
1498:
1487:
1447:
1429:
1320:
1309:
1239:
1213:
1204:
1179:
1153:
1144:
1111:
1067:
1036:
1029:
349:. Metals, too, can engage in multiple bonding in a
406:can be used to predict the nature of the bonding.
194:The type of bonding can be explained in terms of
307:. Conjugation can be found in systems such as
1287:
981:
8:
841:: CS1 maint: multiple names: authors list (
731:: CS1 maint: multiple names: authors list (
860:
858:
856:
1495:
1317:
1294:
1280:
1272:
1210:
1150:
1033:
988:
974:
966:
845:) CS1 maint: numeric names: authors list (
735:) CS1 maint: numeric names: authors list (
1686:Polyhedral skeletal electron pair theory
413:
276:is shorter than the C−C length in
678:
224:
103:
834:
724:
404:Carter-Goddard-Malrieu-Trinquier model
373:are now known for all of the heavier
7:
105:Chemical compounds with double bonds
756:(Ninth ed.). Boston, MA, USA.
410:Types of double bonds between atoms
99:addition reactions of the halogens
25:
1019:Introduction to quantum mechanics
796:Carey, Francis A., 1937- (2007).
692:(3rd ed.). New York: Wiley.
686:March, Jerry, 1929-1997. (1985).
327:, two double bonds are adjacent.
1478:
1472:
1466:
251:
239:
227:
163:
145:
127:
109:
824:from the original on 2024-04-04
778:from the original on 2024-04-04
714:from the original on 2019-12-10
269:With 133 pm, the ethylene
1:
939:Chemistry: A European Journal
330:Double bonds are common for
202:each carbon atom has three
1728:
1384:Metal–ligand multiple bond
909:Royal Society of Chemistry
799:Advanced organic chemistry
351:metal ligand multiple bond
347:elements of higher periods
319:, conjugation can lead to
1464:
1004:
361:Double bonded compounds,
1206:Molecular orbital theory
357:Group 14 alkene homologs
905:Chemical Communications
345:, and less common with
182:Double bonds in alkenes
46:as opposed to two in a
951:10.1002/chem.200401299
191:
196:orbital hybridisation
189:
1374:Coordinate (dipolar)
190:Geometry of ethylene
1548:C–H···O interaction
1330:Electron deficiency
1146:Valence bond theory
220:cis-trans isomerism
1533:Resonance-assisted
192:
153:Dimethyl sulfoxide
84:Alexander Butlerov
1699:
1698:
1650:Electron counting
1621:
1620:
1510:London dispersion
1462:
1461:
1439:Metal aromaticity
1269:
1268:
1265:
1264:
1240:Constituent units
1221:Molecular orbital
1200:
1199:
1180:Constituent units
1140:
1139:
1014:Quantum mechanics
879:10.1021/cr9408989
873:(12): 3463–3504.
809:978-0-387-44897-8
763:978-1-305-08048-5
753:Organic chemistry
670:
669:
473:alkylidenesilanes
332:period 2 elements
305:conjugated system
206:orbitals and one
174:Nitrogen-nitrogen
44:bonding electrons
16:(Redirected from
1719:
1712:Chemical bonding
1691:Jemmis mno rules
1543:Dihydrogen bonds
1496:
1482:
1476:
1470:
1404:Hyperconjugation
1318:
1296:
1289:
1282:
1273:
1211:
1151:
1132:Exchange-coupled
1034:
997:Chemical bonding
990:
983:
976:
967:
962:
929:
928:
917:10.1039/B908048A
900:
891:
890:
867:Chemical Reviews
862:
851:
850:
840:
832:
830:
829:
793:
787:
786:
784:
783:
747:
741:
740:
730:
722:
720:
719:
683:
496:nitroso compound
414:
317:cyclic molecules
255:
243:
231:
175:
167:
157:
149:
139:
131:
121:
113:
72:skeletal formula
30:In chemistry, a
21:
1727:
1726:
1722:
1721:
1720:
1718:
1717:
1716:
1702:
1701:
1700:
1695:
1644:
1617:
1560:
1552:
1514:
1501:
1491:
1483:
1477:
1471:
1458:
1443:
1425:
1313:
1305:
1300:
1270:
1261:
1235:
1196:
1175:
1171:Lewis structure
1136:
1107:
1063:
1025:
1000:
994:
945:(12): 3511–20.
936:
933:
932:
902:
901:
894:
864:
863:
854:
833:
827:
825:
810:
795:
794:
790:
781:
779:
764:
750:McMurry, John.
749:
748:
744:
723:
717:
715:
700:
685:
684:
680:
675:
412:
400:
396:
392:
388:
384:
380:
372:
368:
359:
301:
265:
256:
247:
244:
235:
232:
184:
177:
173:
168:
159:
155:
150:
141:
137:
132:
123:
119:
114:
42:involving four
28:
23:
22:
15:
12:
11:
5:
1725:
1723:
1715:
1714:
1704:
1703:
1697:
1696:
1694:
1693:
1688:
1683:
1682:
1681:
1676:
1671:
1666:
1655:
1653:
1646:
1645:
1643:
1642:
1637:
1631:
1629:
1623:
1622:
1619:
1618:
1616:
1615:
1610:
1605:
1600:
1595:
1590:
1580:
1575:
1570:
1564:
1562:
1554:
1553:
1551:
1550:
1545:
1540:
1535:
1530:
1524:
1522:
1516:
1515:
1513:
1512:
1506:
1504:
1493:
1489:Intermolecular
1485:
1484:
1465:
1463:
1460:
1459:
1457:
1456:
1453:
1451:
1445:
1444:
1442:
1441:
1435:
1433:
1427:
1426:
1424:
1423:
1422:
1421:
1416:
1406:
1401:
1396:
1391:
1386:
1381:
1376:
1371:
1366:
1361:
1360:
1359:
1349:
1348:
1347:
1342:
1337:
1326:
1324:
1315:
1311:Intramolecular
1307:
1306:
1303:Chemical bonds
1301:
1299:
1298:
1291:
1284:
1276:
1267:
1266:
1263:
1262:
1260:
1259:
1257:Antibonding MO
1254:
1252:Non-bonding MO
1249:
1243:
1241:
1237:
1236:
1234:
1233:
1228:
1223:
1217:
1215:
1208:
1202:
1201:
1198:
1197:
1195:
1194:
1189:
1183:
1181:
1177:
1176:
1174:
1173:
1168:
1163:
1161:Hybrid orbital
1157:
1155:
1148:
1142:
1141:
1138:
1137:
1135:
1134:
1129:
1124:
1118:
1116:
1109:
1108:
1106:
1105:
1100:
1095:
1090:
1085:
1080:
1074:
1072:
1065:
1064:
1062:
1061:
1056:
1051:
1046:
1040:
1038:
1031:
1030:Types of bonds
1027:
1026:
1024:
1023:
1022:
1021:
1011:
1009:Atomic orbital
1005:
1002:
1001:
995:
993:
992:
985:
978:
970:
964:
963:
931:
930:
892:
852:
808:
788:
762:
742:
698:
677:
676:
674:
671:
668:
667:
662:
660:
658:
656:
654:
652:
650:
648:
644:
643:
641:
636:
634:
632:
630:
628:
626:
624:
620:
619:
617:
615:
610:
608:
606:
604:
602:
600:
596:
595:
593:
591:
589:
584:
582:
580:
578:
576:
572:
571:
569:
567:
565:
563:
558:
556:
554:
552:
548:
547:
545:
543:
541:
539:
537:
532:
530:
528:
524:
523:
521:
519:
517:
515:
498:
493:
488:
486:
482:
481:
479:
477:
475:
470:
461:
456:
454:carbonyl group
451:
446:
442:
441:
438:
435:
432:
429:
426:
423:
420:
417:
411:
408:
398:
394:
390:
386:
385:CHSn=SnCH(SiMe
382:
378:
370:
366:
358:
355:
300:
297:
267:
266:
257:
250:
248:
245:
238:
236:
233:
226:
183:
180:
179:
178:
169:
162:
160:
151:
144:
142:
133:
126:
124:
115:
108:
106:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1724:
1713:
1710:
1709:
1707:
1692:
1689:
1687:
1684:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1664:Hückel's rule
1662:
1661:
1660:
1657:
1656:
1654:
1651:
1647:
1641:
1638:
1636:
1633:
1632:
1630:
1628:
1627:Bond cleavage
1624:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1593:Intercalation
1591:
1588:
1584:
1583:Metallophilic
1581:
1579:
1576:
1574:
1571:
1569:
1566:
1565:
1563:
1559:
1555:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1525:
1523:
1521:
1517:
1511:
1508:
1507:
1505:
1503:
1500:Van der Waals
1497:
1494:
1490:
1486:
1481:
1475:
1469:
1455:
1454:
1452:
1450:
1446:
1440:
1437:
1436:
1434:
1432:
1428:
1420:
1417:
1415:
1412:
1411:
1410:
1407:
1405:
1402:
1400:
1397:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1358:
1355:
1354:
1353:
1350:
1346:
1343:
1341:
1338:
1336:
1333:
1332:
1331:
1328:
1327:
1325:
1323:
1319:
1316:
1312:
1308:
1304:
1297:
1292:
1290:
1285:
1283:
1278:
1277:
1274:
1258:
1255:
1253:
1250:
1248:
1245:
1244:
1242:
1238:
1232:
1229:
1227:
1224:
1222:
1219:
1218:
1216:
1212:
1209:
1207:
1203:
1193:
1190:
1188:
1187:Covalent bond
1185:
1184:
1182:
1178:
1172:
1169:
1167:
1164:
1162:
1159:
1158:
1156:
1152:
1149:
1147:
1143:
1133:
1130:
1128:
1125:
1123:
1120:
1119:
1117:
1115:
1110:
1104:
1101:
1099:
1098:5 (quintuple)
1096:
1094:
1093:4 (quadruple)
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1075:
1073:
1071:
1066:
1060:
1057:
1055:
1052:
1050:
1047:
1045:
1042:
1041:
1039:
1035:
1032:
1028:
1020:
1017:
1016:
1015:
1012:
1010:
1007:
1006:
1003:
998:
991:
986:
984:
979:
977:
972:
971:
968:
960:
956:
952:
948:
944:
940:
935:
934:
926:
922:
918:
914:
911:: 5201–5213.
910:
906:
899:
897:
893:
888:
884:
880:
876:
872:
868:
861:
859:
857:
853:
848:
844:
838:
823:
819:
815:
811:
805:
801:
800:
792:
789:
777:
773:
769:
765:
759:
755:
754:
746:
743:
738:
734:
728:
713:
709:
705:
701:
699:0-471-88841-9
695:
691:
690:
682:
679:
672:
666:
663:
661:
659:
657:
655:
653:
651:
649:
646:
645:
642:
640:
637:
635:
633:
631:
629:
627:
625:
622:
621:
618:
616:
614:
611:
609:
607:
605:
603:
601:
598:
597:
594:
592:
590:
588:
585:
583:
581:
579:
577:
574:
573:
570:
568:
566:
564:
562:
559:
557:
555:
553:
550:
549:
546:
544:
542:
540:
538:
536:
533:
531:
529:
526:
525:
522:
520:
518:
516:
514:
513:sulfonic acid
510:
509:sulfinic acid
506:
502:
499:
497:
494:
492:
489:
487:
484:
483:
480:
478:
476:
474:
471:
469:
465:
462:
460:
457:
455:
452:
450:
447:
444:
443:
439:
436:
433:
430:
427:
424:
421:
418:
416:
415:
409:
407:
405:
376:
364:
356:
354:
352:
348:
344:
340:
336:
333:
328:
326:
322:
318:
314:
310:
306:
298:
296:
294:
289:
287:
283:
279:
275:
272:
264:
260:
254:
249:
242:
237:
230:
225:
223:
221:
217:
213:
209:
205:
201:
197:
188:
181:
172:
166:
161:
156:Sulfur-oxygen
154:
148:
143:
138:Carbon-oxygen
136:
130:
125:
120:Carbon-carbon
118:
112:
107:
104:
102:
100:
96:
92:
87:
85:
81:
77:
73:
69:
65:
61:
60:azo compounds
57:
53:
49:
45:
41:
37:
36:covalent bond
33:
19:
1669:Baird's rule
1389:Charge-shift
1352:Hypervalence
1103:6 (sextuple)
1082:
1070:multiplicity
942:
938:
904:
870:
866:
826:. Retrieved
798:
791:
780:. Retrieved
752:
745:
716:. Retrieved
688:
681:
535:azo compound
360:
329:
302:
290:
268:
193:
91:single bonds
88:
70:(S=O). In a
38:between two
31:
29:
1659:Aromaticity
1635:Heterolysis
1613:Salt bridge
1558:Noncovalent
1528:Low-barrier
1409:Aromaticity
1399:Conjugation
1379:Pi backbond
1037:By symmetry
365:homologs, R
321:aromaticity
274:bond length
261:(green) in
176:double bond
158:double bond
140:double bond
122:double bond
76:equals sign
66:(C=N), and
48:single bond
32:double bond
18:Double-bond
1587:aurophilic
1568:Mechanical
1247:Bonding MO
1231:MO diagram
1088:3 (triple)
1083:2 (double)
1078:1 (single)
828:2020-12-12
782:2020-12-12
718:2020-12-12
673:References
464:thioketone
299:Variations
212:sigma bond
95:bond order
68:sulfoxides
1679:spherical
1640:Homolysis
1603:Cation–pi
1578:Chalcogen
1538:Symmetric
1394:Hapticity
1192:Lone pair
1166:Resonance
1054:Delta (δ)
1044:Sigma (σ)
837:cite book
818:154040953
772:907259297
727:cite book
665:plumbenes
639:stannenes
501:sulfoxide
325:cumulenes
293:bent bond
208:p-orbital
1706:Category
1608:Anion–pi
1598:Stacking
1520:Hydrogen
1431:Metallic
1322:Covalent
1314:(strong)
1214:Concepts
1154:Concepts
959:15832398
925:19707626
887:11849028
822:Archived
776:Archived
712:Archived
708:10998226
613:germenes
561:disulfur
491:dioxygen
375:group 14
339:nitrogen
263:ethylene
200:ethylene
117:Ethylene
82:chemist
56:carbonyl
1573:Halogen
1419:bicyclo
1364:Agostic
1127:Singlet
1122:Triplet
1059:Phi (φ)
587:silenes
505:sulfone
259:pi bond
216:pi bond
171:Diazene
135:Acetone
80:Russian
62:(N=N),
52:alkenes
1674:Möbius
1502:forces
1492:(weak)
1049:Pi (π)
999:theory
957:
923:
907:(35).
885:
816:
806:
770:
760:
706:
696:
449:alkene
363:alkene
343:oxygen
341:, and
335:carbon
313:enones
309:dienes
284:
278:ethane
93:. The
64:imines
1652:rules
1561:other
1449:Ionic
1357:3c–4e
1345:8c–2e
1340:4c–2e
1335:3c–2e
468:thial
459:imine
323:. In
315:. In
198:. In
40:atoms
34:is a
1414:homo
1369:Bent
1226:LCAO
1114:spin
955:PMID
921:PMID
883:PMID
847:link
843:link
814:OCLC
804:ISBN
768:OCLC
758:ISBN
737:link
733:link
704:OCLC
694:ISBN
369:E=ER
311:and
1112:By
1068:By
947:doi
913:doi
875:doi
647:Pb
623:Sn
599:Ge
575:Si
440:Pb
437:Sn
434:Ge
431:Si
397:Si)
381:Si)
286:mol
271:C=C
101:).
1708::
953:.
943:11
941:.
919:.
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881:.
871:99
869:.
855:^
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835:{{
820:.
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774:.
766:.
729:}}
725:{{
710:.
702:.
551:S
527:N
511:,
507:,
503:,
485:O
466:,
445:C
428:S
425:N
422:O
419:C
353:.
337:,
295:.
282:kJ
204:sp
86:.
1589:)
1585:(
1295:e
1288:t
1281:v
989:e
982:t
975:v
961:.
949::
927:.
915::
889:.
877::
849:)
831:.
785:.
739:)
721:.
399:2
395:3
391:2
389:)
387:3
383:2
379:3
371:2
367:2
20:)
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