Knowledge (XXG)

Catenation

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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.
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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
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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".
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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".
398:, unlike its neighbor carbon, is much less likely to form chains that are stable at room temperature. Some examples of which are solid nitrogen, 448:
molecules. On heating these rings open and link together giving rise to increasingly long chains, as evidenced by the progressive increase in
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chains of atoms than heavier elements which bond via higher valence shell orbitals. Catenation ability is also influenced by a range of
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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
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O, for example, shows catenated hydrogen bonding between the hydroxyl groups, leading to the formation of helical chains; crystalline
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Salaudeen, A. Abibat; Kilnera, C.A.; Halcrow, M.A. (2008). "A crystalline hydrogen-bonded network with a poly-catenate topology".
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atoms covalently link to each other to form an icosahedral structure. Various other similar motifs are also well studied, such as
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decreases with increases in the number of silicon atoms. Silanes higher in molecular weight than disilane decompose to polymeric
1055:"Structure and spectroscopy of phosphorus cluster anions: Theory (simulated annealing) and experiment (photoelectron detachment)" 992:
Forstel, Maksyutenko, Jones, Sun, Chen, Chang, & Kaiser. "Detection of the Elusive Triazane Molecule () in the Gas Phase",
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In recent years a variety of double and triple bonds between the semi-metallic elements have been reported, including silicon,
932:"Polynitrogen Chemistry. Synthesis, Characterization, and Crystal Structure of Surprisingly Stable Fluoroantimonate Salts of 931: 879:
Akira Sekiguchi; Rei Kinjo; Masaaki Ichinohe (September 2004). "A Stable Compound Containing a Silicon-Silicon Triple Bond".
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A polycatenated network, with rings formed from metal-templated hemispheres linked by hydrogen bonds, was reported in 2008.
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that can only form unstable polyfluorides at low temperature, all other stable halogens (Cl, Br, I) can form several
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Karni, M.; Apeloig, Y. (January 2002). "The quest for a stable silyne, RSi≡CR′. The effect of bulky substituents".
316:. But with a suitable pair of organic substituents in place of hydrogen on each silicon it is possible to prepare 581: 414:, have been synthesized. These compounds have potential use as a convenient way to store large amount of energy. 425:
chains (with organic substituents) have been prepared, although these tend to be quite fragile. Small rings or
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Vij, Ashwani; William W. Wilson; Vandana Vij; Fook S. Tham; Jeffrey A. Sheehy; Karl O. Christe (9 Jun 2001).
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and so on. The ability of certain main group elements to catenate is currently the subject of research into
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Even silicon–silicon pi bonds are possible. However, these bonds are less stable than the carbon analogues.
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Shriver, Atkins. Inorganic Chemistry, Fifth Edition. W. H. Freeman and Company, New York, 2010; pp 416
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W. W. Porterfield, Inorganic Chemistry: A Unified Approach, 2nd Ed.", Academic Press (1993), p. 219.
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However, carbon is by no means the only element capable of forming such catenae, and several other
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In unusual conditions, a 1-dimensional series of hydrogen molecules confined within a single wall
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is the parent of this class of compounds). However, it is difficult to prepare and isolate Si
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of the element to itself, which decreases with more diffuse orbitals (those with higher
630: 521: 329: 705: 1141: 1008:"1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N 10 Chain" 561: 531: 192: 121: 59: 916: 865: 783: 647: 603: 426: 384: 134: 30: 971: 512:. In all these anions, the halogen atoms of the same element bond to each other. 224:
involve three-dimensional networks of tetrahedra and chains and rings, linked via
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is built up from molecules connected by hydrogen bonds, forming infinite chains.
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that are stable at room temperature, of which the most prominent example being
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ordinary hydrogen, a pressure which is difficult to access experimentally.
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Inorganic Chemistry, Holleman-Wiberg, John Wiley & Sons (2001) p. 844.
324:. These long chain compounds have surprising electronic properties - high 501: 461: 407: 399: 395: 360: 348: 336: 313: 289: 157: 138: 129:
essentially being the study of catenated carbon structures (and known as
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Jones, R. O.; Ganteför, G.; Hunsicker, S.; Pieperhoff, P. (1995-12-08).
830: 363:, long thought to be too unstable to be isolated were reported in 2004. 485: 481: 376: 317: 285: 191:) overlapping to form the bond. Hence, carbon, with the least diffuse 177: 165: 1023: 959: 586: 1071: 1054: 670: 452:
as the chains lengthen. Also, sulfur polycations, sulfur polyanions (
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is largely due to catenation. In the native state, sulfur exists as
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Derissen, JL (1974). "The crystal structure of isophthalic acid".
403: 372: 320:(sometimes, erroneously called polysilenes) that are analogues of 161: 29: 410:. Even longer series with eight nitrogen atoms or more, such as 183:
The ability of an element to catenate is primarily based on the
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are capable of forming an expansive range of catenae, including
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Wiberg, Egon; Wiberg, Nils; Holleman, Arnold Frederick (2001).
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Miller, R. D.; Michl, J. (1989). "Polysilane high polymers".
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Bonding of atoms of the same element into chains or rings
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Head-Gordon, Teresa; Johnson, Margaret E. (June 2006).
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Klapötke, Thomas M.; Piercey, Davin G. (2011-04-04).
1102: 604:"Tetrahedral structure or chains for liquid water" 288:can form sigma bonds to other silicon atoms (and 608:Proceedings of the National Academy of Sciences 137:combine any of various other elements, such as 82:if its ends are not bonded to each other (an 8: 468:show variants of these structural motifs. 195:p orbital is capable of forming longer p-p 1070: 629: 619: 304:) with n greater than about 8, as their 573: 203:and electronic factors, including the 437:The versatile chemistry of elemental 351:and disilynes are quite rare, unlike 7: 116:Catenation occurs most readily with 587:http://www.oed.com/view/Entry/30197 328:, for example - arising from sigma 300:(analogous to the saturated alkane 1103:Wiberg, Wiberg & Holleman 2001 371:In dodecaborate(12) anion, twelve 25: 207:of the element in question, the 90:if they are bonded in a ring (a 1059:The Journal of Chemical Physics 343:are quite reactive compared to 332:of the electrons in the chain. 149:, onto the backbone of carbon. 1: 1123:. San Diego: Academic Press. 706:10.1016/S0040-4039(00)01903-1 38:molecule, consisting of nine 768:10.1021/acs.nanolett.9b00258 460:are all known. Furthermore, 527:Chain-growth polymerization 1169: 412:1,1'-Azobis-1,2,3-triazole 733:10.1107/S0567740872004844 582:Oxford English Dictionary 189:azimuthal quantum number 70:into a series, called a 901:10.1126/science.1102209 858:10.1023/A:1016091614005 621:10.1073/pnas.0510593103 326:electrical conductivity 102:reflect the Latin root 592:'chain', definition 4g 585:, 1st edition (1889) [ 47: 42:atoms in a chain with 506:isopolyhalogen anions 472:Semimetallic elements 33: 974:on 23 September 2017 133:). Carbon chains in 46:atoms surrounding it 1153:Inorganic chemistry 1121:Inorganic Chemistry 1012:Inorganic Chemistry 893:2004Sci...305.1755S 887:(5691): 1755–1757. 831:10.1021/cr00096a006 760:2019NanoL..19.2537X 694:Tetrahedron Letters 458:lower sulfur oxides 385:metal dicarbollides 310:polysilicon hydride 154:main-group elements 84:open-chain compound 490:inorganic polymers 222:structure of water 48: 1148:Organic chemistry 1130:978-0-12-352651-9 1065:(22): 9549–9562. 1024:10.1021/ic200071q 996:, 2015, 16, 3139. 960:10.1021/ja010141g 954:(26): 6308–6313. 846:Silicon Chemistry 665:(41): 5200–5202. 614:(21): 7973–7977. 557:Inorganic polymer 429:are more common. 306:thermal stability 236:organic chemistry 209:molecular orbital 205:electronegativity 127:organic chemistry 16:(Redirected from 1160: 1134: 1106: 1100: 1094: 1091: 1085: 1084: 1074: 1072:10.1063/1.469969 1050: 1044: 1043: 1018:(7): 2732–2734. 1003: 997: 990: 984: 983: 981: 979: 970:. Archived from 948:J. Am. Chem. Soc 943: 942: 941: 927: 921: 920: 876: 870: 869: 841: 835: 834: 818:Chemical Reviews 812: 806: 803: 797: 794: 788: 787: 754:(4): 2537–2542. 743: 737: 736: 721:Acta Crystallogr 716: 710: 709: 689: 683: 682: 671:10.1039/B810393C 658: 652: 651: 633: 623: 599: 593: 578: 542:Polyhalogen ions 496:Halogen elements 252:isophthalic acid 226:hydrogen bonding 220:Theories of the 21: 1168: 1167: 1163: 1162: 1161: 1159: 1158: 1157: 1138: 1137: 1131: 1118: 1115: 1110: 1109: 1101: 1097: 1092: 1088: 1052: 1051: 1047: 1005: 1004: 1000: 991: 987: 977: 975: 940: 937: 936: 935: 933: 929: 928: 924: 878: 877: 873: 843: 842: 838: 814: 813: 809: 804: 800: 795: 791: 745: 744: 740: 727:(6): 764–2765. 718: 717: 713: 691: 690: 686: 660: 659: 655: 601: 600: 596: 579: 575: 570: 518: 498: 474: 446: 435: 420: 393: 369: 299: 295: 283: 271:carbon nanotube 265: 261: 257: 249: 245: 218: 114: 92:cyclic compound 74:. A chain or a 28: 23: 22: 15: 12: 11: 5: 1166: 1164: 1156: 1155: 1150: 1140: 1139: 1136: 1135: 1129: 1114: 1111: 1108: 1107: 1105:, p. 422. 1095: 1086: 1045: 998: 985: 938: 922: 871: 836: 807: 798: 789: 738: 711: 700:(2): 319–322. 684: 653: 594: 572: 571: 569: 566: 565: 564: 559: 554: 549: 544: 539: 534: 529: 524: 522:Backbone chain 517: 514: 497: 494: 473: 470: 444: 434: 431: 419: 416: 392: 389: 368: 365: 359:. Examples of 341:longer silanes 330:delocalization 297: 293: 282: 279: 263: 259: 255: 247: 243: 217: 214: 122:covalent bonds 120:, which forms 113: 110: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 1165: 1154: 1151: 1149: 1146: 1145: 1143: 1132: 1126: 1122: 1117: 1116: 1112: 1104: 1099: 1096: 1090: 1087: 1082: 1078: 1073: 1068: 1064: 1060: 1056: 1049: 1046: 1041: 1037: 1033: 1029: 1025: 1021: 1017: 1013: 1009: 1002: 999: 995: 989: 986: 973: 969: 965: 961: 957: 953: 949: 945: 926: 923: 918: 914: 910: 906: 902: 898: 894: 890: 886: 882: 875: 872: 867: 863: 859: 855: 851: 847: 840: 837: 832: 828: 824: 820: 819: 811: 808: 802: 799: 793: 790: 785: 781: 777: 773: 769: 765: 761: 757: 753: 749: 742: 739: 734: 730: 726: 722: 715: 712: 707: 703: 699: 695: 688: 685: 680: 676: 672: 668: 664: 663:Chem. Commun. 657: 654: 649: 645: 641: 637: 632: 627: 622: 617: 613: 609: 605: 598: 595: 591: 588: 584: 583: 577: 574: 567: 563: 562:Self-assembly 560: 558: 555: 553: 550: 548: 545: 543: 540: 538: 535: 533: 532:Macromolecule 530: 528: 525: 523: 520: 519: 515: 513: 511: 507: 503: 495: 493: 491: 487: 483: 479: 471: 469: 467: 463: 459: 455: 451: 447: 440: 432: 430: 428: 424: 417: 415: 413: 409: 405: 401: 397: 390: 388: 386: 382: 378: 374: 366: 364: 362: 358: 354: 350: 346: 342: 338: 333: 331: 327: 323: 319: 315: 311: 307: 303: 291: 287: 280: 278: 276: 272: 267: 253: 241: 240:4-tricyclanol 237: 232: 229: 227: 223: 215: 213: 210: 206: 202: 198: 194: 193:valence shell 190: 186: 181: 179: 175: 171: 167: 163: 159: 155: 150: 148: 144: 140: 136: 132: 128: 123: 119: 111: 109: 107: 106: 101: 97: 94:). The words 93: 89: 85: 81: 78:shape may be 77: 73: 69: 65: 61: 57: 53: 45: 41: 37: 32: 19: 1120: 1113:Bibliography 1098: 1089: 1062: 1058: 1048: 1015: 1011: 1001: 994:ChemPhysChem 993: 988: 976:. Retrieved 972:the original 951: 947: 925: 884: 880: 874: 852:(1): 59–65. 849: 845: 839: 822: 816: 810: 801: 792: 751: 747: 741: 724: 720: 714: 697: 693: 687: 662: 656: 611: 607: 597: 589: 580: 576: 547:Polysulfides 499: 475: 454:polysulfides 436: 421: 394: 370: 334: 302:hydrocarbons 284: 268: 233: 230: 219: 197:sigma bonded 182: 151: 135:biochemistry 130: 115: 103: 99: 95: 87: 79: 71: 66:of the same 55: 49: 18:Carbon chain 825:(6): 1359. 537:Aromaticity 500:Except for 404:azide anion 318:polysilanes 185:bond energy 108:, "chain". 96:to catenate 1142:Categories 568:References 423:Phosphorus 418:Phosphorus 381:carboranes 170:phosphorus 100:catenation 56:catenation 1081:0021-9606 1032:0020-1669 978:21 August 748:Nano Lett 552:Superatom 510:triiodide 478:germanium 466:tellurium 450:viscosity 408:triazoles 361:disilynes 275:metallize 147:biometals 52:chemistry 1040:21384800 968:11427055 917:24416825 909:15375262 866:97098444 784:83460656 776:30884943 679:18956068 648:20023418 640:16698934 516:See also 502:fluorine 462:selenium 427:clusters 400:triazane 396:Nitrogen 391:Nitrogen 349:Disilene 337:Disilane 314:hydrogen 290:disilane 216:Hydrogen 178:halogens 158:hydrogen 139:hydrogen 44:hydrogen 889:Bibcode 881:Science 756:Bibcode 631:1472414 486:bismuth 482:arsenic 377:boranes 357:alkynes 353:alkenes 345:alkanes 322:alkanes 286:Silicon 281:Silicon 166:silicon 131:catenae 68:element 60:bonding 58:is the 1127:  1079:  1038:  1030:  966:  915:  907:  864:  782:  774:  677:  646:  638:  628:  456:) and 439:sulfur 433:Sulfur 201:steric 174:sulfur 145:, and 143:oxygen 118:carbon 112:Carbon 105:catena 88:closed 86:), or 40:carbon 36:nonane 913:S2CID 862:S2CID 780:S2CID 644:S2CID 373:boron 367:Boron 162:boron 72:chain 64:atoms 1125:ISBN 1077:ISSN 1036:PMID 1028:ISSN 980:2022 964:PMID 905:PMID 772:PMID 675:PMID 636:PMID 590:s.v. 464:and 406:and 383:and 355:and 339:and 312:and 298:2n+2 176:and 98:and 80:open 76:ring 1067:doi 1063:103 1020:doi 956:doi 952:123 897:doi 885:305 854:doi 827:doi 764:doi 729:doi 725:B30 702:doi 667:doi 626:PMC 616:doi 612:103 234:In 172:, 62:of 50:In 1144:: 1075:. 1061:. 1057:. 1034:. 1026:. 1016:50 1014:. 1010:. 962:. 950:. 946:. 911:. 903:. 895:. 883:. 860:. 848:. 823:89 821:. 778:. 770:. 762:. 752:19 750:. 723:. 698:47 696:. 673:. 642:. 634:. 624:. 610:. 606:. 492:. 484:, 480:, 402:, 387:. 379:, 347:. 248:16 244:10 228:. 180:. 168:, 164:, 160:, 141:, 54:, 34:A 1133:. 1083:. 1069:: 1042:. 1022:: 982:. 958:: 944:" 939:5 934:N 919:. 899:: 891:: 868:. 856:: 850:1 833:. 829:: 786:. 766:: 758:: 735:. 731:: 708:. 704:: 681:. 669:: 650:. 618:: 445:8 443:S 296:H 294:n 264:4 262:O 260:6 258:H 256:8 254:C 246:H 242:C 20:)

Index

Carbon chain

nonane
carbon
hydrogen
chemistry
bonding
atoms
element
ring
open-chain compound
cyclic compound
catena
carbon
covalent bonds
organic chemistry
biochemistry
hydrogen
oxygen
biometals
main-group elements
hydrogen
boron
silicon
phosphorus
sulfur
halogens
bond energy
azimuthal quantum number
valence shell

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