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1142: 1737: 858: 807: 853: 683: 504: 1157: 1543: 1152: 790: 1538: 884: 1957: 509: 1732: 1162: 1861: 448: 499: 696: 104: 1015: 109: 453: 725: 443: 2038: 1962: 1851: 165: 1580: 678: 738: 377: 160: 2028: 2164: 1147: 1942: 1856: 215: 1005: 170: 2033: 1727: 1322: 751: 384: 1952: 1846: 1327: 1947: 1010: 1332: 55:
Greenwood & Earnshaw, p. 207: instructive to compare B-N compounds with their C-C counterparts, since they are isoelectronic and have similar sizes and electronegativities (ish)
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RB≡NR′ (R, R′ = long alkyl chains) polymerise at 25 °C to colourless waxy materials - they may be polymers, but are poorly characterised
465: 857: 432:, is in reversible equilibrium between monomer and dimer in the gas phase, and can cyclotrimerise to cyclotriborazane in the solid state. 987: 852: 682: 806: 503: 1156: 1542: 1151: 1478:
Crystal structure shows Si non-planar, but slightly pyramidal, due to appreciable π-σ* mixing, which is not seen in alkenes:
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tBu-B≡N-tBu reacts with at 25 °C to form the complex , in which the iminoborane bonds to niobium side-on:
724: 452: 442: 39:"Chemistry of the Main Group Elements, Part 2: Rings, Chains and Macromolecules, Based on Main Group Elements" 21: 2037: 1961: 1295: 643: 103: 1850: 1831: 1346: 108: 1827: 1631: 164: 1080: 1074: 1050: 1799: 1704: 1579: 677: 2027: 1043: 737: 376: 159: 1875: 1823: 1374: 1291: 922: 591: 2163: 1883: 1146: 994:
and not thermodynamically stable with respect to HCl or water addition - Housecroft 3rd edn. p. 355)
2058: 1819: 1815: 1528: 774: 471: 1941: 1303: 1998: 1351: 1206: 1855: 1030: 214: 1569: 1096: 2054: 2032: 1682: 1651: 1004: 169: 17: 1715:, formally a trimer of the hypothetical molecule phosphonitrile dichloride (1832-07-1), N≡PCl 464:
Dehydrocoupling amine-borane adducts to cyclic aminoboranes and borazines at 25 °C with
1726: 43: 1321: 1227:) - many structures, either discrete anions or anionic chains and rings - contain planar BO 184:
The bonding in B-N compounds can be confusing. Amine-borane adducts can be represented as R
1951: 1920: 1916: 1903: 1845: 1811: 1751: 1307: 1270: 750: 383: 1993: 196:, the charges are meant to be relative to the charges in the separate neutral fragments R 91: 1946: 1326: 897:
Iminoboranes can undergo addition across their BN groups — e.g. RB≡NR′ + HCl → RClB=NHR′
1976: 1896: 1835: 1299: 1220: 1009: 825: 147: 572: 1912: 1765: 1694: 1360: 647: 79: 1892: 1426: 1407: 1243: 1239: 1517: 2010: 1607: 1595: 1417:(review, including π-σ* mixing MO diagram accounting for pyramidalization of Si) 1364: 1176: 1641:
G&E p. 536: Produced industrially by R. Schenk and G. Römer's 1924 method:
1369: 1356: 1331: 1066: 763: 562: 532: 1558: 1401:, thermally stable yellow or orange crystalline solids if R groups are bulky 622: 611: 193: 1490: 1186:- reluctant to crystallise, consists of 3D network with trigonal planar BO 762:
Tert-butyl(tert-butylimino)borane, tBu-B≡N-tBu, B-N distance 1.26 Å,
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but significant ΔEN means electron density more localised on nitrogen
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N has a large δ−, which is reduced to a small δ− upon formation of R
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has a large δ+, which decreases to a small δ+ upon formation of R
238:. The negative charge on N decreases, but is still negative. 424:
ring compounds are known. For example, aminoborane itself, H
259:. The positive charge on B decreases, but is still positive. 1926:
S-O polymers pretty useless because they all hydrolyse to H
1610:: compounds with PN multiple bonds (at least formally) 399:), aminoboranes tend to cyclise and readily hydrolyse 267:
Calculated partial charges (Spartan, MP2, 6–311+G**)
990:
characteristic of benzene (although benzene is only
416:
rings due to steric hindrance, but some 6-membered B
1508:
Recent calculated structures of disilene itself, Si
1461:(cyclotrisilane) → (UV radiation, −60 °C) (R 1238:Many molecular B-O species, e.g. hydrolysis of 8: 408:Aminoboranes usually cyclise to 4-membered B 42:If you like this sort of thing, you'll like 1590:the first carbon substituted disilyne: 2008 982:tends to undergo addition (e.g. of HCl or H 520:Other catalysts include colloidal rhodium ( 395:Without bulky substituents (i.e. without 967:— formally a trimer of iminoborane, HBNH 265: 2132:forms adducts with Lewis acids, e.g. S 1425:First disilene, tetramesityldisilene: 7: 979:only weak delocalisation/aromaticity 988:electrophilic aromatic substitution 986:O across BN bonds) rather than the 32: 2162: 2036: 2031: 2026: 1960: 1955: 1950: 1945: 1940: 1859: 1854: 1849: 1844: 1735: 1730: 1725: 1578: 1541: 1536: 1330: 1325: 1320: 1160: 1155: 1150: 1145: 1140: 1013: 1008: 1003: 882: 856: 851: 805: 788: 749: 736: 723: 694: 681: 676: 507: 502: 497: 451: 446: 441: 382: 375: 213: 168: 163: 158: 107: 102: 1427:R. West, M. J. Fink, J. Michl, 1029:Phosphine-borane adducts, e.g. 204:, but this is still misleading. 1: 1909:(monomer, trimer and polymer) 1776:(n = 3, 4) → (250 °C) → (NPCl 1602:Phosphorus–nitrogen chemistry 139:nice, stable compounds e.g. H 1359:, sigma delocalisation c.f. 1806:Phosphorus–oxygen chemistry 1341:Catenated silicon chemistry 1312:ring-opening polymerization 2183: 1024:Boron–phosphorus chemistry 824:BN) cyclodimerises to the 2114:, 25 °C, slow → (SN) 2096:, heat over Ag wool → 2 S 1971:Sulfur–nitrogen chemistry 1784:(n = lots) → (Nu) → (NPNu 1697:solvent, 120–150 °C) 970:has six π electrons like 339: 325: 311: 297: 289: 283: 273: 1265:Silicon–oxygen chemistry 50:Boron–nitrogen chemistry 1870:Sulfur–oxygen chemistry 1832:sodium tripolyphosphate 1397:, silicon analogues of 1347:Organosilicon chemistry 1260:linear B-O polymers yet 1042:Phosphinoboranes, e.g. 78:Two main polymorphs of 1828:tripolyphosphoric acid 1171:Boron–oxygen chemistry 1098:Angew. Chem., Int. Ed. 773:(Shelf 20 in library, 1800:Living polymerization 1705:Hexachlorophosphazene 1409:Adv. Organomet. Chem. 1296:Rochow-Müller process 820:tBu-B≡N-tBu (i.e. tBu 624:Angew. Chem. Int. Ed. 613:Angew. Chem. Int. Ed. 610:at 25 °C : 397:kinetic stabilisation 86:-like) and cubic BN ( 1878:: Cyclooctasulfur, S 1824:phosphorus pentoxide 1764:+ Cl → (120-150 °C, 1081:Polyphosphinoboranes 644:Brookhart's catalyst 118:Amine-borane adducts 2059:disulfur dichloride 1820:phosphorus trioxide 1816:pyrophosphoric acid 1615:Cyclic phosphazenes 1231:triangles and/or BO 1051:Boraphosphabenzenes 931:parent compound is 590:Dehydrogenation to 574:J. Organomet. Chem. 268: 1352:Hexamethyldisilane 1310:, thermal anionic 1207:borosilicate glass 354: 266: 247:Similarly, B in BR 2055:ammonium chloride 2047:Synthesis of (SN) 1519:Chem. Phys. Lett. 1418: 1110:J. Am. Chem. Soc. 580:, 2849–2853 538:J. Am. Chem. Soc. 523:J. Am. Chem. Soc. 353: 352: 264: 92:explore with Jmol 68:, c.f. elemental 56: 18:User:Benjah-bmm27 2174: 2166: 2040: 2035: 2030: 1964: 1959: 1954: 1949: 1944: 1876:Catenated sulfur 1863: 1858: 1853: 1848: 1768:solvent) → (NPCl 1752:polyphosphazenes 1746:Polyphosphazenes 1739: 1734: 1729: 1582: 1545: 1540: 1406: 1375:Polycarbosilanes 1334: 1329: 1324: 1164: 1159: 1154: 1149: 1144: 1017: 1012: 1007: 947:or equivalently 886: 860: 855: 809: 792: 753: 740: 727: 698: 685: 680: 592:polyaminoboranes 559:Polyaminoboranes 553:Polyaminoboranes 511: 506: 501: 455: 450: 445: 386: 379: 269: 217: 172: 167: 162: 111: 106: 82:, hexagonal BN ( 54: 35:Main group 2, IM 2182: 2181: 2177: 2176: 2175: 2173: 2172: 2171: 2155: 2151: 2147: 2143: 2139: 2135: 2131: 2127: 2119: 2113: 2109: 2103: 2099: 2095: 2091: 2085: 2081: 2077: 2073: 2069: 2052: 2016: 2006: 2002: 1990: 1986: 1977:Sulfur nitrides 1973: 1933: 1929: 1921:disulfuric acid 1917:sulfur oxoacids 1907: 1900: 1889: 1881: 1872: 1836:polynucleotides 1812:Phosphoric acid 1808: 1791: 1787: 1783: 1779: 1775: 1771: 1763: 1748: 1718: 1714: 1710: 1677: 1671: 1666: 1655: 1629: 1623: 1617: 1604: 1551: 1515: 1511: 1492:Heteroat. Chem. 1481:Organometallics 1468: 1464: 1460: 1456: 1452: 1448: 1396: 1392: 1383: 1343: 1308:silicone rubber 1271:Silicon dioxide 1267: 1259: 1249: 1234: 1230: 1221:borate minerals 1204: 1200: 1196: 1189: 1184: 1180: 1173: 1093:Manners et al: 1090: 1086: 1083:, e.g. (PHPh-BH 1072: 1064: 1046: 1038: 1034: 1026: 985: 966: 958: 954: 946: 942: 938: 915: 839: 835: 831: 823: 707: 657:Organometallics 653: 609: 605: 601: 597: 555: 479: 475: 468: 431: 427: 423: 419: 415: 411: 359: 293: 287: 281: 277: 258: 254: 250: 237: 233: 229: 203: 199: 191: 187: 178: 146: 142: 120: 62: 52: 37: 30: 29: 28: 12: 11: 5: 2180: 2178: 2170: 2169: 2168: 2167: 2157: 2156: 2153: 2149: 2145: 2141: 2137: 2133: 2129: 2125: 2121: 2120: 2115: 2111: 2107: 2104: 2101: 2097: 2093: 2089: 2086: 2083: 2079: 2075: 2071: 2067: 2063: 2062: 2048: 2044: 2043: 2042: 2041: 2021: 2020: 2019: 2018: 2012: 2008: 2004: 2000: 1996: 1988: 1984: 1972: 1969: 1968: 1967: 1966: 1965: 1935: 1934: 1931: 1927: 1924: 1910: 1905: 1898: 1890: 1887: 1884:plastic sulfur 1879: 1871: 1868: 1867: 1866: 1865: 1864: 1839: 1838: 1807: 1804: 1803: 1802: 1796: 1795: 1794: 1793: 1789: 1785: 1781: 1777: 1773: 1769: 1761: 1755: 1754: 1747: 1744: 1743: 1742: 1741: 1740: 1720: 1719: 1716: 1712: 1708: 1701: 1700: 1699: 1698: 1688: 1687: 1686: 1685: 1673: 1669: 1664: 1653: 1643: 1642: 1639: 1625: 1621: 1616: 1613: 1612: 1611: 1603: 1600: 1599: 1598: 1586: 1585: 1584: 1583: 1573: 1572: 1570:view with Jmol 1550: 1547: 1534: 1533: 1532: 1531: 1529:Jmol structure 1513: 1509: 1503: 1502: 1501: 1500: 1473: 1472: 1471: 1470: 1466: 1462: 1458: 1454: 1450: 1446: 1440: 1439: 1438: 1437: 1420: 1419: 1403: 1402: 1394: 1390: 1382: 1379: 1378: 1377: 1372: 1367: 1354: 1349: 1342: 1339: 1338: 1337: 1336: 1335: 1315: 1314: 1300:Direct process 1281: 1266: 1263: 1262: 1261: 1257: 1254: 1247: 1236: 1232: 1228: 1214: 1202: 1198: 1194: 1191: 1187: 1182: 1178: 1172: 1169: 1168: 1167: 1166: 1165: 1135: 1134: 1133: 1132: 1131: 1130: 1122:Macromolecules 1118: 1106: 1088: 1084: 1078: 1075:view with Jmol 1070: 1062: 1048: 1044: 1040: 1036: 1032: 1025: 1022: 1021: 1020: 1019: 1018: 998: 997: 996: 995: 983: 980: 977: 974: 968: 964: 956: 952: 944: 940: 936: 926: 925: 914: 911: 910: 909: 908: 907: 901: 900: 899: 898: 892: 891: 890: 889: 888: 887: 875: 874: 873: 872: 866: 865: 864: 863: 862: 861: 844: 843: 842: 841: 837: 833: 829: 826:cyclobutadiene 821: 815: 814: 813: 812: 811: 810: 798: 797: 796: 795: 794: 793: 781: 780: 779: 778: 757: 756: 755: 754: 744: 743: 742: 741: 731: 730: 729: 728: 718: 717: 706: 703: 702: 701: 700: 699: 689: 688: 687: 686: 671: 670: 669: 668: 667: 666: 651: 635: 634: 633: 632: 607: 603: 599: 595: 585: 584: 583: 582: 566: 565: 554: 551: 550: 549: 548: 547: 515: 514: 513: 512: 492: 491: 490: 489: 487:(2001) 962-963 477: 473: 466: 459: 458: 457: 456: 436: 435: 434: 433: 429: 425: 421: 417: 413: 409: 403: 402: 401: 400: 390: 389: 388: 387: 380: 370: 369: 358: 355: 351: 350: 347: 344: 341: 337: 336: 333: 330: 327: 323: 322: 319: 316: 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510: 505: 500: 496: 495: 494: 493: 488: 486: 485:Chem. Commun. 481: 469: 463: 462: 461: 460: 454: 449: 444: 440: 439: 438: 437: 407: 406: 405: 404: 398: 394: 393: 392: 391: 385: 381: 378: 374: 373: 372: 371: 368: 364: 361: 360: 356: 348: 345: 342: 338: 334: 331: 328: 324: 320: 317: 314: 310: 306: 303: 300: 296: 271: 270: 246: 245: 244: 243: 225: 224: 223: 222: 216: 212: 211: 210: 209: 195: 183: 182: 181: 180: 179: 171: 166: 161: 157: 156: 155: 154: 149: 138: 137: 136: 135: 132: 128: 127: 124:Amine-borane 122: 121: 117: 110: 105: 101: 100: 99: 98: 93: 89: 85: 81: 80:boron nitride 77: 76: 75: 74: 71: 67: 66:Boron nitride 64: 63: 60:Boron nitride 59: 57: 49: 47: 45: 40: 34: 27: 23: 19: 2116: 2082:+ 16 HCl + S 2049: 2013: 1679: 1674: 1659: 1648: 1635: 1626: 1608:Phosphazenes 1596:Silabenzenes 1587: 1563: 1559: 1535: 1522: 1518: 1495: 1491: 1484: 1480: 1432: 1428: 1412: 1408: 1304:silicone gum 1274: 1125: 1121: 1113: 1109: 1101: 1097: 1054: 991: 960: 948: 918: 828:analogue tBu 768: 764: 711:Iminoboranes 710: 705:Iminoboranes 660: 656: 627: 623: 616: 612: 577: 573: 558: 541: 537: 526: 522: 484: 363:Aminoboranes 362: 357:Aminoboranes 177: 123: 65: 53: 44:this article 41: 38: 1792:(n > 10) 1566:, 1755-1757 1435:, 1343-1344 1370:Polysilynes 1365:lithography 1357:Polysilanes 1242:leading to 1116:, 6669–6678 1104:, 3321-3323 992:kinetically 771:, 1089-1102 663:, 1766-1776 630:, 9600-9602 619:, 6212-6215 602:→ (-NHMe-BH 594:, e.g. MeNH 563:polyolefins 544:, 9582–9583 533:titanocenes 529:, 9776–9785 482:catalysts: 2066:4 Cl + 6 S 1915:and other 1638:= 3, 4, 5) 1469:(disilene) 1235:tetrahedra 765:Chem. Ber. 192:. In this 1555:Disilynes 1549:Disilynes 1487:, 793–800 1453:+ Li → (R 1387:Disilenes 1381:Disilenes 1284:Siloxanes 1256:No high-M 1252:boroxines 1128:, 291–297 919:Borazines 913:Borazines 654:complex: 194:formalism 90:-like) - 1588:Update: 1415:, 73-148 933:borazine 200:N and BR 84:graphite 24:‎ | 20:‎ | 1707:, (NPCl 1668:→ (NPCl 1562:(2004) 1560:Science 1525:, 11-15 1521:(2008) 1494:(1990) 1483:(1984) 1431:(1981) 1429:Science 1411:(2006) 1399:alkenes 1290:, e.g. 1217:Borates 1124:(2003) 1112:(2000) 1100:(1999) 1053:, e.g. 972:benzene 963:-(HBNH) 921:, c.f. 767:(1984) 715:alkynes 713:, c.f. 659:(2004) 642:(using 626:(2008) 615:(2008) 576:(2007) 561:, c.f. 540:(2006) 525:(2004) 367:alkenes 365:, c.f. 349:−0.113 343:−0.122 335:+0.338 329:−0.058 318:−0.998 315:−0.412 304:+0.335 301:+0.279 131:alkanes 129:, c.f. 126:adducts 88:diamond 1393:Si=SiR 1279:quartz 1250:, and 1246:RB(OH) 1223:(e.g. 923:arenes 531:) and 226:N in R 70:carbon 22:degree 2053:from 1620:(NPCl 1498:, 1-7 1225:borax 1211:Pyrex 1201:+ SiO 1190:units 1055:cyclo 1035:P→BCl 961:cyclo 951:-(BH) 949:cyclo 16:< 2140:+ BF 2057:and 2011:(SN) 1994:Jmol 1882:and 1766:PhCl 1695:PhCl 1632:Jmol 1449:SiCl 1292:PDMS 1286:and 1219:and 955:(NH) 775:Jmol 650:-IrH 646:, a 472:RhCl 470:and 278:N–BH 255:N→BR 234:N→BR 188:N-BR 143:N→BH 2152:·BF 2144:→ S 2074:→ S 1886:, S 1760:PCl 1683:HCl 1678:+ 4 1663:PCl 1564:305 1523:466 1465:Si) 1457:Si) 1433:214 1389:: R 1302:), 1114:122 1059:Mes 1057:-(B 959:or 935:, B 769:117 598:·BH 578:692 542:128 527:126 476:.3H 428:NBH 340:BH 298:NH 2070:Cl 1992:: 1979:: 1930:SO 1919:: 1904:SO 1902:, 1897:SO 1895:: 1834:, 1830:, 1826:, 1822:, 1818:, 1814:, 1658:+ 1656:Cl 1652:NH 1630:: 1568:, 1557:: 1527:, 1516:: 1489:, 1413:54 1363:, 1306:, 1294:, 1273:– 1205:→ 1126:36 1102:38 1067:Cy 1065:(P 1031:Ph 661:23 628:47 621:, 617:47 606:-) 346:— 332:— 326:B 321:— 312:N 307:— 290:BH 284:NH 46:. 2154:3 2150:4 2148:N 2146:4 2142:3 2138:4 2136:N 2134:4 2130:4 2128:N 2126:4 2124:S 2117:x 2112:2 2110:N 2108:2 2106:S 2102:2 2100:N 2098:2 2094:4 2092:N 2090:4 2088:S 2084:8 2080:4 2078:N 2076:4 2072:2 2068:2 2061:: 2050:x 2014:x 2005:2 2003:N 2001:2 1999:S 1989:4 1987:N 1985:4 1983:S 1932:4 1928:2 1923:\ 1906:3 1899:2 1888:n 1880:8 1790:n 1788:) 1786:2 1782:n 1780:) 1778:2 1774:n 1772:) 1770:2 1762:5 1717:2 1713:3 1711:) 1709:2 1693:( 1680:n 1675:n 1672:) 1670:2 1665:5 1660:n 1654:4 1649:n 1636:n 1634:( 1627:n 1624:) 1622:2 1514:4 1512:H 1510:2 1496:1 1485:3 1467:2 1463:2 1459:3 1455:2 1451:2 1447:2 1445:R 1395:2 1391:2 1298:( 1277:- 1275:α 1258:w 1248:2 1233:4 1229:3 1213:) 1209:( 1203:2 1199:3 1197:O 1195:2 1193:B 1188:3 1183:3 1181:O 1179:2 1177:B 1089:n 1087:) 1085:2 1077:) 1073:( 1071:3 1069:) 1063:3 1061:) 1045:4 1037:3 1033:3 984:2 965:3 957:3 953:3 945:6 943:H 941:3 939:N 937:3 840:: 838:2 836:N 834:2 832:B 830:4 822:2 777:) 665:) 652:2 608:n 604:2 600:3 596:2 546:) 535:( 480:O 478:2 474:3 467:2 430:2 426:2 422:3 420:N 418:3 414:2 412:N 410:2 292:3 286:3 280:3 276:3 274:H 257:3 253:3 249:3 236:3 232:3 228:3 202:3 198:3 190:3 186:3 145:3 141:3 26:2

Index

User:Benjah-bmm27
degree
2
this article
carbon
boron nitride
graphite
diamond
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adducts
alkanes
ammonia borane



formalism

alkenes


kinetic stabilisation



2
RhCl3.3H2O
Chem. Commun. (2001) 962-963

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