698:
Xiong, Y.; Yao, S.; Driess, M. (2013). "Chemical Tricks To
Stabilize Silanones and Their Heavier Homologues with EO Bonds (E=Si–Pb): From Elusive Species to Isolable Building Blocks".
110:
of 1.90 and oxygen 3.44. The electronegativity difference between the elements is therefore 1.54. Because of this moderately large difference in electronegativities, the
897:
Barrow, M. J.; Ebsworth, E. A. V.; Harding, M. M. (1979). "The crystal and molecular structures of disiloxane (at 108 K) and hexamethyldisiloxane (at 148 K)".
864:
Vojinović, Krunoslav; Losehand, Udo; Mitzel, Nobert W. (2004). "Dichlorosilane–dimethyl ether aggregation: a new motif in halosilane adduct formation".
185:
containing two Si=O double bonds would polymerise. Other compounds containing Si=O double bonds are normally very reactive and unstable with respect to
607:
Dankert, Fabian; von Hänisch, Carsten (2021). "Siloxane
Coordination Revisited: Si–O Bond Character, Reactivity and Magnificent Molecular Shapes".
386:
is typically 107–113°. Si–O–C groups are intermediate, tending to have bond angles smaller than Si–O–Si but larger than C–O–C. The main reasons are
103:
1071:
820:
736:
700:
609:
126:
have an electronegativity difference of 0.89 and are less polar than silicon–oxygen bonds. Silicon–oxygen bonds are therefore
1049:
940:
682:
652:
586:
78:. Compounds containing silicon–oxygen bonds include materials of major geological and industrial significance such as
1106:
999:
993:
Bogey, Marcel; Delcroix, Bruno; Jean-Claude
Guillemin, Adam Walters (1996). "Experimentally Determined Structure of H
977:
899:
770:
Sun, T.; Li, J.; Wang, H. (2022). "Recent
Advances in the Chemistry of Heavier Group 14 Analogues of Carbonyls".
382:
than their carbon counterparts, C–O–C. The Si–O–Si angle ranges from about 130–180°, whereas the C–O–C angle in
497:
493:
394:
734:
Sen, S. S. (2014). "A Stable
Silanone with a Three-Coordinate Silicon Atom: A Century-Long Wait is Over".
472:
as the size and coordination number of the lanthanide decreases from neodymium to lutetium. It is 150° in
772:
67:
1165:
244:
1124:
532:
522:
527:
517:
154:
123:
401:
between the two neighbouring partially positive silicon atoms). Recent calculations suggest π
1041:
578:
202:
1007:
477:
201:
unless they are stabilised, for example by coordination to a metal centre, coordination to
161:
are weaker than carbon–oxygen double bonds (590 vs. 715 kJ mol) due to a better overlap of
91:
8:
866:
501:
481:
55:
1011:
816:"An Isolable Silicon Analogue of a Ketone that Contains an Unperturbed Si=O Double Bond"
1141:
846:
793:
625:
409:
makes only a minor contribution to bonding as the Si 3d orbital is too high in energy.
43:
181:
is a polymeric solid containing four Si–O single bonds per silicon atom; molecular SiO
1122:
Glidewell, C.; Liles, D. C. (1978). "The crystal and molecular structure of oxobis".
1102:
1045:
973:
936:
879:
850:
838:
797:
785:
752:
716:
678:
648:
629:
582:
537:
131:
115:
107:
83:
63:
1145:
1133:
1079:
1033:
1015:
965:
908:
871:
828:
777:
744:
708:
617:
570:
387:
206:
170:
47:
492:
In silicate minerals, silicon often forms single bonds to four oxygen atoms in a
425:
190:
178:
398:
186:
174:
150:
135:
1137:
912:
1159:
127:
119:
71:
31:
1083:
1019:
883:
842:
833:
815:
789:
781:
756:
748:
720:
712:
621:
473:
445:
421:
413:
177:
is a molecular gas containing two C=O double bonds per carbon atom whereas
1065:
Schnöckel, Hansgeorg (1978). "IR Spectroscopic
Detection of Molecular SiO
957:
417:
402:
158:
142:
969:
505:
391:
379:
375:
75:
964:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons, Ltd.
875:
406:
194:
162:
198:
146:
87:
51:
992:
429:
166:
35:
138:
on silicon and a partial negative charge on oxygen: Si—O.
79:
39:
383:
997:
SiO by
Rotational Spectroscopy and Isotopic Substitution".
814:
Kobayashi, Ryo; Ishida, Shintaro; Iwamoto, Takeaki (2019).
59:
956:
Kaftory, Menahem; Kapon, Moshe; Botoshansky, Mark (1998).
62:, with oxygen taking the larger share due to its greater
809:
807:
602:
600:
598:
955:
935:(6th ed.). John Wiley & Sons. pp. 24–25.
863:
16:
Covalent chemical bond between silicon and oxygen atoms
813:
1026:
958:"The Structural Chemistry of Organosilicon Compounds"
896:
804:
595:
258:
Pauling electronegativity difference between E and O
97:
1099:
Silicon
Chemistry: From the Atom to Extended Systems
962:
The
Chemistry of Organic Silicon Compounds, Volume 2
460:. It increases progressively from 133° to 180° in Ln
677:. Oxford University Press. pp. 50–52, 65–67.
606:
1032:
647:(3rd ed.). Prentice Hall. pp. 413–424.
569:
390:(donation from an oxygen p orbital to an Si–R σ*
1157:
642:
1121:
960:. In Rappoport, Zvi; Apeloig, Yitzhak (eds.).
697:
500:. At high pressures, silicon can increase its
70:means Si–O bonds show characteristics of both
1096:
122:. Carbon has an electronegativity of 2.55 so
672:
675:Periodicity and the s- and p-Block Elements
930:
397:, for example) and ionic effects (such as
358:Typical E=O double bond strength / kJ mol
347:Typical E–O single bond strength / kJ mol
1064:
832:
769:
643:Housecroft, C. E.; Sharpe, A. G. (2008).
636:
565:
563:
561:
559:
557:
555:
553:
169:in the latter. This is an example of the
986:
931:Smith, Michael B.; March, Jerry (2007).
926:
924:
922:
668:
666:
664:
1097:Jutzi, Peter; Schubert, Ulrich (2003).
405:from an oxygen 2p orbital to a silicon
1158:
550:
487:
157:single bonds. However, silicon–oxygen
1090:
919:
661:
378:groups, Si–O–Si, tend to have larger
733:
13:
933:March's Advanced Organic Chemistry
149:) but stronger (452 vs. about 360
98:Bond polarity, length and strength
14:
1177:
213:Comparison of C–O and Si–O bonds
42:atoms that can be found in many
1115:
1058:
949:
890:
104:Pauling electronegativity scale
857:
763:
727:
691:
494:tetrahedral molecular geometry
370:
1:
1101:. Wiley-VCH. pp. 27–28.
543:
412:The Si–O–Si angle is 144° in
395:antibonding molecular orbital
50:. In a silicon–oxygen bond,
7:
511:
336:E=O double bond length / Å
321:E=O double bond length / Å
307:E–O single bond length / Å
292:E–O single bond length / Å
10:
1182:
498:silicon–oxygen tetrahedron
1138:10.1107/S0567740878002435
1044:. pp. 292, 304–314.
1038:Chemistry of the Elements
1036:; Earnshaw, Alan (1997).
913:10.1107/S0567740879008529
575:Chemistry of the Elements
573:; Earnshaw, Alan (1997).
432:(another polymorph of SiO
245:Pauling electronegativity
399:electrostatic repulsion
145:are longer (1.6 vs 1.4
136:partial positive charge
1084:10.1002/anie.197806161
1020:10.1006/jmsp.1996.0048
834:10.1002/anie.201905198
782:10.1002/asia.202200611
749:10.1002/anie.201404793
713:10.1002/anie.201209766
622:10.1002/ejic.202100275
518:Organosilicon compound
1072:Angew. Chem. Int. Ed.
1042:Butterworth-Heinemann
1034:Greenwood, Norman N.
821:Angew. Chem. Int. Ed.
737:Angew. Chem. Int. Ed.
701:Angew. Chem. Int. Ed.
673:N. C. Norman (1997).
579:Butterworth-Heinemann
571:Greenwood, Norman N.
444:, and in the ion in
173:. For these reasons,
610:Eur. J. Inorg. Chem.
581:. pp. 342–366.
533:Carbon–fluorine bond
523:Carbon–hydrogen bond
478:lithium metasilicate
203:Lewis acids or bases
92:polydimethylsiloxane
1125:Acta Crystallogr. B
1012:1996JMoSp.175..421B
900:Acta Crystallogr. B
645:Inorganic Chemistry
502:coordination number
488:Coordination number
482:sodium metasilicate
214:
165:forming a stronger
124:carbon–oxygen bonds
21:silicon–oxygen bond
1000:J. Mol. Spectrosc.
970:10.1002/0470857250
528:Carbon–carbon bond
212:
1051:978-0-08-037941-8
942:978-0-471-72091-1
870:(16): 2578–2581.
827:(28): 9425–9428.
743:(34): 8820–8822.
707:(16): 4302–4311.
684:978-0-19-855961-0
654:978-0-13-175553-6
616:(29): 2907–2927.
588:978-0-08-037941-8
538:Bonding in solids
424:and (153±20)° in
368:
367:
108:electronegativity
106:, silicon has an
88:silicone polymers
84:silicate minerals
64:electronegativity
48:organic compounds
1173:
1166:Chemical bonding
1150:
1149:
1119:
1113:
1112:
1094:
1088:
1087:
1062:
1056:
1055:
1040:(2nd ed.).
1030:
1024:
1023:
990:
984:
983:
953:
947:
946:
928:
917:
916:
907:(9): 2093–2099.
894:
888:
887:
876:10.1039/B405684A
861:
855:
854:
836:
811:
802:
801:
767:
761:
760:
731:
725:
724:
695:
689:
688:
670:
659:
658:
640:
634:
633:
604:
593:
592:
577:(2nd ed.).
567:
428:. It is 180° in
388:hyperconjugation
215:
211:
207:steric shielding
171:double bond rule
113:
58:between the two
56:shared unequally
27:
1181:
1180:
1176:
1175:
1174:
1172:
1171:
1170:
1156:
1155:
1154:
1153:
1120:
1116:
1109:
1095:
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1068:
1063:
1059:
1052:
1031:
1027:
996:
991:
987:
980:
954:
950:
943:
929:
920:
895:
891:
862:
858:
812:
805:
768:
764:
732:
728:
696:
692:
685:
671:
662:
655:
641:
637:
605:
596:
589:
568:
551:
546:
514:
490:
471:
467:
463:
459:
455:
451:
443:
439:
435:
426:vitreous silica
373:
277:Bond angle / °
276:
272:
197:oligomerise to
191:oligomerization
184:
179:silicon dioxide
141:Silicon–oxygen
111:
100:
25:
17:
12:
11:
5:
1179:
1169:
1168:
1152:
1151:
1114:
1107:
1089:
1078:(8): 616–617.
1066:
1057:
1050:
1025:
1006:(2): 421–428.
994:
985:
978:
948:
941:
918:
889:
856:
803:
776:: e202200611.
773:Chem. Asian J.
762:
726:
690:
683:
660:
653:
635:
594:
587:
548:
547:
545:
542:
541:
540:
535:
530:
525:
520:
513:
510:
504:to six, as in
489:
486:
469:
465:
461:
457:
453:
449:
441:
437:
433:
422:α-cristobalite
372:
369:
366:
365:
362:
359:
355:
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344:
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329:
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241:
240:
237:
234:
230:
229:
227:Silicon–oxygen
224:
219:
187:polymerisation
182:
175:carbon dioxide
118:but not fully
99:
96:
15:
9:
6:
4:
3:
2:
1178:
1167:
1164:
1163:
1161:
1147:
1143:
1139:
1135:
1131:
1127:
1126:
1118:
1110:
1108:9783527306473
1104:
1100:
1093:
1085:
1081:
1077:
1074:
1073:
1061:
1053:
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1039:
1035:
1029:
1021:
1017:
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1009:
1005:
1002:
1001:
989:
981:
979:9780471967576
975:
971:
967:
963:
959:
952:
944:
938:
934:
927:
925:
923:
914:
910:
906:
902:
901:
893:
885:
881:
877:
873:
869:
868:
867:Dalton Trans.
860:
852:
848:
844:
840:
835:
830:
826:
823:
822:
817:
810:
808:
799:
795:
791:
787:
783:
779:
775:
774:
766:
758:
754:
750:
746:
742:
739:
738:
730:
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718:
714:
710:
706:
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702:
694:
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623:
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584:
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566:
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531:
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257:
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242:
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228:
225:
223:
222:Carbon–oxygen
220:
217:
216:
210:
208:
204:
200:
196:
192:
188:
180:
176:
172:
168:
164:
160:
156:
155:carbon–oxygen
152:
148:
144:
139:
137:
133:
129:
125:
121:
117:
109:
105:
95:
93:
89:
85:
81:
77:
73:
69:
65:
61:
57:
53:
49:
45:
41:
37:
33:
32:chemical bond
29:
22:
1129:
1123:
1117:
1098:
1092:
1075:
1070:
1060:
1037:
1028:
1003:
998:
988:
961:
951:
932:
904:
898:
892:
865:
859:
824:
819:
771:
765:
740:
735:
729:
704:
699:
693:
674:
644:
638:
613:
608:
574:
496:, forming a
491:
476:and 134° in
474:hemimorphite
446:thortveitite
411:
374:
333:
318:
304:
289:
226:
221:
159:double bonds
143:single bonds
140:
101:
68:polarisation
24:
20:
18:
1132:: 124–128.
403:backbonding
380:bond angles
371:Bond angles
76:ionic bonds
544:References
506:stishovite
420:, 147° in
416:, 155° in
407:3d orbital
376:Disiloxane
163:p orbitals
851:157056381
798:251104394
630:239645449
440:Si–O–SiPh
199:siloxanes
195:Silanones
134:, with a
52:electrons
44:inorganic
1160:Category
1146:98347658
884:15303175
843:31095845
790:35883252
757:24990653
721:23450830
512:See also
436:), in Ph
418:β-quartz
414:α-quartz
332:Typical
317:Typical
303:Typical
288:Typical
205:, or by
128:covalent
114:bond is
72:covalent
34:between
1008:Bibcode
430:coesite
167:pi bond
153:) than
102:On the
66:. This
36:silicon
30:) is a
1144:
1105:
1048:
976:
939:
882:
849:
841:
796:
788:
755:
719:
681:
651:
628:
585:
384:ethers
273:E–O–EH
151:kJ mol
80:silica
40:oxygen
1142:S2CID
847:S2CID
794:S2CID
626:S2CID
392:sigma
350:~360
342:1.48
339:1.16
327:1.52
324:1.21
310:1.34
298:1.63
295:1.43
264:1.54
261:0.89
253:1.90
250:2.55
247:of E
218:Bond
132:polar
120:ionic
116:polar
90:like
60:atoms
1103:ISBN
1046:ISBN
974:ISBN
937:ISBN
880:PMID
839:PMID
786:PMID
753:PMID
717:PMID
679:ISBN
649:ISBN
614:2021
583:ISBN
480:and
448:, Sc
364:590
361:715
353:452
283:142
280:111
130:and
112:Si−O
86:and
74:and
54:are
46:and
38:and
28:bond
26:Si−O
1134:doi
1080:doi
1069:".
1016:doi
1004:175
966:doi
909:doi
872:doi
829:doi
778:doi
745:doi
709:doi
618:doi
239:Si
189:or
1162::
1140:.
1130:34
1128:.
1076:17
1014:.
972:.
921:^
905:35
903:.
878:.
845:.
837:.
825:58
818:.
806:^
792:.
784:.
751:.
741:53
715:.
705:52
663:^
624:.
597:^
552:^
508:.
484:.
464:Si
452:Si
334:sp
319:sp
305:sp
290:sp
236:C
233:E
209:.
193:.
94:.
82:,
19:A
1148:.
1136::
1111:.
1086:.
1082::
1067:2
1054:.
1022:.
1018::
1010::
995:2
982:.
968::
945:.
915:.
911::
886:.
874::
853:.
831::
800:.
780::
759:.
747::
723:.
711::
687:.
657:.
632:.
620::
591:.
470:7
468:O
466:2
462:2
458:7
456:O
454:2
450:2
442:3
438:3
434:2
275:3
271:3
269:H
183:2
147:Å
23:(
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