20:
200:
n and the ability to form different kinds of covalent bonds. For carbon, the sigma overlap between adjacent atoms is sufficiently strong that perfectly stable chains can be formed. With other elements this was once thought to be extremely difficult in spite of plenty of evidence to the contrary.
113:
with other carbon atoms to form longer chains and structures. This is the reason for the presence of the vast number of organic compounds in nature. Carbon is most well known for its properties of catenation, with
735:
Xia, Y. Abibat; Yang, B.; Jin, F.; Ma, Y.; Liu, X.; Zhao, M. (2019). "Hydrogen confined in a single wall carbon nanotube becomes a metallic and superconductive nanowire under high pressure".
681:
Morris, D.G. Abibat; Ryder, K.S.; Walker, A.; Muir, K.W; Hix, G.B; Maclean, E.J (2001). "Unusual synthesis and crystal structure of 4-tricyclanol".
387:, unlike its neighbor carbon, is much less likely to form chains that are stable at room temperature. Some examples of which are solid nitrogen,
437:
molecules. On heating these rings open and link together giving rise to increasingly long chains, as evidenced by the progressive increase in
1117:
188:
chains of atoms than heavier elements which bond via higher valence shell orbitals. Catenation ability is also influenced by a range of
262:
is expected to become metallic at a relatively low pressure of 163.5 GPa. This is about 40% of the ~400 GPa thought to be required to
239:
O, for example, shows catenated hydrogen bonding between the hydroxyl groups, leading to the formation of helical chains; crystalline
329:
650:
Salaudeen, A. Abibat; Kilnera, C.A.; Halcrow, M.A. (2008). "A crystalline hydrogen-bonded network with a poly-catenate topology".
364:
atoms covalently link to each other to form an icosahedral structure. Various other similar motifs are also well studied, such as
297:
decreases with increases in the number of silicon atoms. Silanes higher in molecular weight than disilane decompose to polymeric
1044:"Structure and spectroscopy of phosphorus cluster anions: Theory (simulated annealing) and experiment (photoelectron detachment)"
981:
Forstel, Maksyutenko, Jones, Sun, Chen, Chang, & Kaiser. "Detection of the
Elusive Triazane Molecule () in the Gas Phase",
465:
In recent years a variety of double and triple bonds between the semi-metallic elements have been reported, including silicon,
921:"Polynitrogen Chemistry. Synthesis, Characterization, and Crystal Structure of Surprisingly Stable Fluoroantimonate Salts of
920:
868:
Akira
Sekiguchi; Rei Kinjo; Masaaki Ichinohe (September 2004). "A Stable Compound Containing a Silicon-Silicon Triple Bond".
220:
A polycatenated network, with rings formed from metal-templated hemispheres linked by hydrogen bonds, was reported in 2008.
400:
1141:
515:
493:
that can only form unstable polyfluorides at low temperature, all other stable halogens (Cl, Br, I) can form several
1136:
833:
Karni, M.; Apeloig, Y. (January 2002). "The quest for a stable silyne, RSi≡CR′. The effect of bulky substituents".
305:. But with a suitable pair of organic substituents in place of hydrogen on each silicon it is possible to prepare
570:
403:, have been synthesized. These compounds have potential use as a convenient way to store large amount of energy.
414:
chains (with organic substituents) have been prepared, although these tend to be quite fragile. Small rings or
177:
919:
Vij, Ashwani; William W. Wilson; Vandana Vij; Fook S. Tham; Jeffrey A. Sheehy; Karl O. Christe (9 Jun 2001).
477:
and so on. The ability of certain main group elements to catenate is currently the subject of research into
324:
Even silicon–silicon pi bonds are possible. However, these bonds are less stable than the carbon analogues.
314:
1082:
Shriver, Atkins. Inorganic
Chemistry, Fifth Edition. W. H. Freeman and Company, New York, 2010; pp 416
877:
744:
431:
785:
W. W. Porterfield, Inorganic
Chemistry: A Unified Approach, 2nd Ed.", Academic Press (1993), p. 219.
446:
298:
228:
210:
141:
However, carbon is by no means the only element capable of forming such catenae, and several other
72:
258:
In unusual conditions, a 1-dimensional series of hydrogen molecules confined within a single wall
901:
850:
768:
632:
142:
135:
1113:
1065:
1024:
1016:
952:
893:
760:
663:
624:
545:
478:
294:
263:
224:
197:
193:
115:
281:
is the parent of this class of compounds). However, it is difficult to prepare and isolate Si
1055:
1008:
944:
885:
842:
815:
806:
752:
717:
690:
655:
614:
604:
530:
494:
240:
214:
64:
56:
259:
80:
881:
748:
176:
of the element to itself, which decreases with more diffuse orbitals (those with higher
619:
510:
318:
694:
1130:
997:"1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N 10 Chain"
550:
520:
181:
110:
48:
905:
854:
772:
636:
592:
415:
373:
123:
19:
960:
501:. In all these anions, the halogen atoms of the same element bond to each other.
213:
involve three-dimensional networks of tetrahedra and chains and rings, linked via
756:
255:
is built up from molecules connected by hydrogen bonds, forming infinite chains.
535:
525:
442:
290:
173:
497:
that are stable at room temperature, of which the most prominent example being
846:
721:
411:
185:
158:
93:
1069:
1020:
996:
227:, hydrogen bonding is known to facilitate the formation of chain structures.
889:
609:
540:
498:
466:
454:
438:
369:
40:
1028:
956:
897:
764:
667:
628:
266:
ordinary hydrogen, a pressure which is difficult to access experimentally.
794:
Inorganic
Chemistry, Holleman-Wiberg, John Wiley & Sons (2001) p. 844.
313:. These long chain compounds have surprising electronic properties - high
490:
450:
396:
388:
384:
349:
337:
325:
302:
278:
146:
127:
118:
essentially being the study of catenated carbon structures (and known as
32:
1042:
Jones, R. O.; Ganteför, G.; Hunsicker, S.; Pieperhoff, P. (1995-12-08).
819:
352:, long thought to be too unstable to be isolated were reported in 2004.
474:
470:
365:
306:
274:
180:) overlapping to form the bond. Hence, carbon, with the least diffuse
166:
154:
1012:
948:
575:
1060:
1043:
659:
441:
as the chains lengthen. Also, sulfur polycations, sulfur polyanions (
427:
345:
341:
333:
310:
189:
162:
131:
106:
28:
24:
430:
is largely due to catenation. In the native state, sulfur exists as
708:
Derissen, JL (1974). "The crystal structure of isophthalic acid".
392:
361:
309:(sometimes, erroneously called polysilenes) that are analogues of
150:
18:
399:. Even longer series with eight nitrogen atoms or more, such as
172:
The ability of an element to catenate is primarily based on the
145:
are capable of forming an expansive range of catenae, including
52:
1108:
Wiberg, Egon; Wiberg, Nils; Holleman, Arnold
Frederick (2001).
804:
Miller, R. D.; Michl, J. (1989). "Polysilane high polymers".
16:
Bonding of atoms of the same element into chains or rings
591:
Head-Gordon, Teresa; Johnson, Margaret E. (June 2006).
995:
Klapötke, Thomas M.; Piercey, Davin G. (2011-04-04).
1091:
593:"Tetrahedral structure or chains for liquid water"
277:can form sigma bonds to other silicon atoms (and
597:Proceedings of the National Academy of Sciences
126:combine any of various other elements, such as
71:if its ends are not bonded to each other (an
8:
457:show variants of these structural motifs.
184:p orbital is capable of forming longer p-p
1059:
618:
608:
293:) with n greater than about 8, as their
562:
192:and electronic factors, including the
426:The versatile chemistry of elemental
340:and disilynes are quite rare, unlike
7:
105:Catenation occurs most readily with
576:http://www.oed.com/view/Entry/30197
317:, for example - arising from sigma
289:(analogous to the saturated alkane
1092:Wiberg, Wiberg & Holleman 2001
360:In dodecaborate(12) anion, twelve
14:
196:of the element in question, the
79:if they are bonded in a ring (a
1048:The Journal of Chemical Physics
332:are quite reactive compared to
321:of the electrons in the chain.
138:, onto the backbone of carbon.
1:
1112:. San Diego: Academic Press.
695:10.1016/S0040-4039(00)01903-1
27:molecule, consisting of nine
757:10.1021/acs.nanolett.9b00258
449:are all known. Furthermore,
516:Chain-growth polymerization
1158:
401:1,1'-Azobis-1,2,3-triazole
722:10.1107/S0567740872004844
571:Oxford English Dictionary
178:azimuthal quantum number
59:into a series, called a
890:10.1126/science.1102209
847:10.1023/A:1016091614005
610:10.1073/pnas.0510593103
315:electrical conductivity
91:reflect the Latin root
581:'chain', definition 4g
574:, 1st edition (1889) [
36:
31:atoms in a chain with
495:isopolyhalogen anions
461:Semimetallic elements
22:
963:on 23 September 2017
122:). Carbon chains in
35:atoms surrounding it
1142:Inorganic chemistry
1110:Inorganic Chemistry
1001:Inorganic Chemistry
882:2004Sci...305.1755S
876:(5691): 1755–1757.
820:10.1021/cr00096a006
749:2019NanoL..19.2537X
683:Tetrahedron Letters
447:lower sulfur oxides
374:metal dicarbollides
299:polysilicon hydride
143:main-group elements
73:open-chain compound
479:inorganic polymers
211:structure of water
37:
1137:Organic chemistry
1119:978-0-12-352651-9
1054:(22): 9549–9562.
1013:10.1021/ic200071q
985:, 2015, 16, 3139.
949:10.1021/ja010141g
943:(26): 6308–6313.
835:Silicon Chemistry
654:(41): 5200–5202.
603:(21): 7973–7977.
546:Inorganic polymer
418:are more common.
295:thermal stability
225:organic chemistry
198:molecular orbital
194:electronegativity
116:organic chemistry
1149:
1123:
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1080:
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1061:10.1063/1.469969
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1007:(7): 2732–2734.
992:
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959:. Archived from
937:J. Am. Chem. Soc
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909:
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859:
858:
830:
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807:Chemical Reviews
801:
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743:(4): 2537–2542.
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710:Acta Crystallogr
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672:
671:
660:10.1039/B810393C
647:
641:
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612:
588:
582:
567:
531:Polyhalogen ions
485:Halogen elements
241:isophthalic acid
215:hydrogen bonding
209:Theories of the
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716:(6): 764–2765.
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260:carbon nanotube
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81:cyclic compound
63:. A chain or a
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12:
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5:
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1094:, p. 422.
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689:(2): 319–322.
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511:Backbone chain
506:
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348:. Examples of
330:longer silanes
319:delocalization
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206:
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111:covalent bonds
109:, which forms
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652:Chem. Commun.
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551:Self-assembly
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521:Macromolecule
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229:4-tricyclanol
226:
221:
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204:
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199:
195:
191:
187:
183:
182:valence shell
179:
175:
170:
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139:
137:
133:
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100:
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96:
95:
90:
86:
83:). The words
82:
78:
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70:
67:shape may be
66:
62:
58:
54:
50:
46:
42:
34:
30:
26:
21:
1109:
1102:Bibliography
1087:
1078:
1051:
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1037:
1004:
1000:
990:
983:ChemPhysChem
982:
977:
965:. Retrieved
961:the original
940:
936:
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873:
869:
863:
841:(1): 59–65.
838:
834:
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713:
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703:
686:
682:
676:
651:
645:
600:
596:
586:
578:
569:
565:
536:Polysulfides
488:
464:
443:polysulfides
425:
410:
383:
359:
323:
291:hydrocarbons
273:
257:
222:
219:
208:
186:sigma bonded
171:
140:
124:biochemistry
119:
104:
92:
88:
84:
76:
68:
60:
55:of the same
44:
38:
814:(6): 1359.
526:Aromaticity
489:Except for
393:azide anion
307:polysilanes
174:bond energy
97:, "chain".
85:to catenate
1131:Categories
557:References
412:Phosphorus
407:Phosphorus
370:carboranes
159:phosphorus
89:catenation
45:catenation
1070:0021-9606
1021:0020-1669
967:21 August
737:Nano Lett
541:Superatom
499:triiodide
467:germanium
455:tellurium
439:viscosity
397:triazoles
350:disilynes
264:metallize
136:biometals
41:chemistry
1029:21384800
957:11427055
906:24416825
898:15375262
855:97098444
773:83460656
765:30884943
668:18956068
637:20023418
629:16698934
505:See also
491:fluorine
451:selenium
416:clusters
389:triazane
385:Nitrogen
380:Nitrogen
338:Disilene
326:Disilane
303:hydrogen
279:disilane
205:Hydrogen
167:halogens
147:hydrogen
128:hydrogen
33:hydrogen
878:Bibcode
870:Science
745:Bibcode
620:1472414
475:bismuth
471:arsenic
366:boranes
346:alkynes
342:alkenes
334:alkanes
311:alkanes
275:Silicon
270:Silicon
155:silicon
120:catenae
57:element
49:bonding
47:is the
1116:
1068:
1027:
1019:
955:
904:
896:
853:
771:
763:
666:
635:
627:
617:
445:) and
428:sulfur
422:Sulfur
190:steric
163:sulfur
134:, and
132:oxygen
107:carbon
101:Carbon
94:catena
77:closed
75:), or
29:carbon
25:nonane
902:S2CID
851:S2CID
769:S2CID
633:S2CID
362:boron
356:Boron
151:boron
61:chain
53:atoms
1114:ISBN
1066:ISSN
1025:PMID
1017:ISSN
969:2022
953:PMID
894:PMID
761:PMID
664:PMID
625:PMID
579:s.v.
453:and
395:and
372:and
344:and
328:and
301:and
287:2n+2
165:and
87:and
69:open
65:ring
1056:doi
1052:103
1009:doi
945:doi
941:123
886:doi
874:305
843:doi
816:doi
753:doi
718:doi
714:B30
691:doi
656:doi
615:PMC
605:doi
601:103
223:In
161:,
51:of
39:In
1133::
1064:.
1050:.
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1023:.
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1005:50
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951:.
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900:.
892:.
884:.
872:.
849:.
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812:89
810:.
767:.
759:.
751:.
741:19
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687:47
685:.
662:.
631:.
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613:.
599:.
595:.
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473:,
469:,
391:,
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368:,
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1072:.
1058::
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928:5
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908:.
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880::
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755::
747::
724:.
720::
697:.
693::
670:.
658::
639:.
607::
434:8
432:S
285:H
283:n
253:4
251:O
249:6
247:H
245:8
243:C
235:H
231:C
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