279:
2234:
2102:
1854:
1610:
2168:
1788:
1666:
1492:
2039:
1976:
1910:
1450:
1230:
1133:
1732:
1178:
274:
1384:
234:
1554:
20:
2329:
1078:
1028:
1297:
289:
547:
of carbon) with the same composition and structure except for the negative charge. As a rule, however, these neutral oxocarbons are less stable than the corresponding anions. Thus, for example, the stable carbonate anion corresponds to the extremely unstable neutral
2579:
Haiyan Chen, Michel Armand, Matthieu Courty, Meng Jiang, Clare P. Grey, Franck Dolhem, Jean-Marie
Tarascon, and Philippe Poizot (2009), "Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery"
285:
In each canonical form there are two single bonds one double bond. The three canonical forms contribute equally to the resonance hybrid, so the three bond C-O bonds have the same length.
2502:
Herman F. Cordes; Herbert P. Richter; Carl A. Heller (1969). "Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate".
482:. However, the anion is often more stable than the acid (as is the case for carbonate); and sometimes the acid is unknown or is expected to be extremely unstable (as is the case of
278:
249:. The three C-O bonds have the same length of 136 pm and the 3 O-C-O angles are 120°. The carbon atom has 4 pairs of valence electrons, which shows that the molecule obeys the
142:. There are however a large number of stable anions in this class, including several ones that have research or industrial use. There are also many unstable anions, like
948:−1. These anions are generally indicated by the prefixes "hydrogen"-, "dihydrogen"-, "trihydrogen"-, etc. Some of them, however, have special names: hydrogencarbonate
808:. The correspondence is not always well-defined since there may be several ways of performing this formal dehydration, including joining two or more anions to make an
257:. The electronic structure is described by two main theories which are used to show how the 4 electron pairs are distributed in a molecule that only has 3 C-O bonds.
350:, may be described as a resonance hybrid of two canonical forms in valence bond theory, or with 2 σ bonds and a delocalized π bond in molecular orbital theory.
42:, one of the oxocarbon anions. Black circles are carbon atoms, red circles are oxygen atoms. Each blue halo represents one half of a negative charge.
2299:
2529:
Schröder, Detlef; Schwarz, Helmut; Dua, Suresh; Blanksby, Stephen J.; Bowie, John H. (May 1999). "Mass spectrometric studies of the oxocarbons C
2150:
2266:
233:
308:
orbitals on the carbon atom with a p orbital on each oxygen atom. In addition, a delocalized π bond is made by overlap of the p
2475:
DeMore W. B.; Jacobsen C. W. (1969). "Formation of carbon trioxide in the photolysis of ozone in liquid carbon dioxide".
2261:
2134:
2216:
1886:
2003:
1642:
2200:
992:
The hydrogenated anions may be stable even if the fully protonated acid is not (as is the case of bicarbonate).
2233:
2129:
2008:
663:
297:
1881:
483:
2101:
1637:
300:
the 3-fold axis is designated as the z axis of the molecule. Three σ bonds are formed overlap of the s, p
2195:
1853:
635:
1609:
2167:
253:. This is one factor that contributes to the high stability of the ion, which occurs in rocks such as
2554:
1052:
816:. Unlike neutralization, this formal dehydration sometimes yields fairly stable oxocarbons, such as
158:, that have a fleeting existence during some chemical reactions; and many hypothetical species, like
2764:
2430:
1838:
1787:
1356:
615:
439:
261:
1665:
1491:
2759:
2685:
2644:
2373:
1764:
1716:
1538:
1432:
1368:
1201:
817:
578:
184:
159:
2038:
1975:
1909:
1449:
1229:
2609:
2086:
2023:
1960:
1477:
1132:
192:
2737:
2694:
2653:
2589:
2562:
2511:
2484:
1731:
1345:
1257:
1218:
1177:
1166:
443:
273:
265:
208:
188:
176:
2066:
1942:
1416:
1158:
1151:
1121:
1061:
1047:
639:
638:
to yield other anions with the same structural formula but greater negative charge. Thus
549:
2558:
1383:
1759:
1586:
1553:
1281:
1210:
1196:
1113:
1066:
801:
2566:
2328:
1077:
1027:
19:
2753:
2361:
1820:
1262:
1101:
853:
590:
467:
427:
328:
2454:
2071:
1698:
1296:
688:
316:
orbital on each oxygen atom which is perpendicular to the plane of the molecule.
172:, that have been the subject of theoretical studies but have yet to be observed.
1937:
1524:
1519:
1411:
1329:
961:
748:
of the corresponding acid. The latter would be another oxocarbon with formula C
335:
320:
242:
2698:
2657:
2434:
1581:
986:
250:
2604:
J. Liebig, F. Wöhler (1830), "Ueber die
Zusammensetzung der Honigsteinsäure"
2420:
2390:
Several other oxocarbon anions have been detected in trace amounts, such as
2356:
1815:
1096:
829:
745:
540:
524:
254:
107:
47:
24:
183:. Unstable anions may persist in very rarefied gaseous state, such as in
2425:
1693:
809:
2515:
2488:
1000:
Here is an incomplete list of the known or conjectured oxocarbon anions
1324:
813:
123:
2741:
2593:
389:
196:
180:
63:
59:
2711:
Richard B. Wyrwas and
Caroline Chick Jarrold (2006), "Production of
2672:
2623:
288:
544:
287:
55:
393:
788:
O. The standard example is the connection between carbonate
523:
can be matched in principle to the electrically neutral (or
292:
making a π-bond between 2 atoms of the same chemical element
232:
2455:"Infrared and mass spectral studies of proton irradiated H
319:
Note that the same bonding schemes may be applied the
16:
Negatively-charged molecule made of carbon and oxygen
442:
or other species; this is the case, for example, of
334:Similarly, the two-fold symmetrical structure of a
264:the electronic structure of the carbonate ion is a
241:The carbonate ion has a trigonal planar structure,
2732:from Oligomerization of CO on Molybdenum Anions".
626:, which has been detected only in trace amounts.
66:atoms, and therefore having the general formula
2325:
2230:
2164:
2098:
2035:
1972:
1906:
1850:
1784:
1728:
1662:
1606:
1550:
1488:
1446:
1380:
1293:
1226:
1174:
1129:
1074:
1024:
904:−1 partially hydrogenated anions with formulas
2686:Berichte der Deutschen Chemischen Gesellschaft
2645:Berichte der Deutschen Chemischen Gesellschaft
8:
2326:
2231:
2165:
2099:
2036:
1973:
1907:
1851:
1785:
1729:
1663:
1607:
1551:
1489:
1447:
1381:
1294:
1227:
1175:
1130:
1075:
1025:
187:. Most oxocarbon anions have corresponding
2411:, a singly ionized version of rhodizonate.
426:, for example, can be seen as the anion of
2547:International Journal of Mass Spectrometry
388:can be seen as the result of removing all
2606:Poggendorfs Annalen der Physik und Chemie
634:Conversely, some oxocarbon anions can be
229:Electronic structure of the carbonate ion
199:. Thus, for example, the oxalate moiety
2736:volume 128 issue 42, pages 13688–13689.
1002:
237:Space-filling model of the carbonate ion
221:
217:
213:
202:
129:
29:
18:
2447:
438:. Sometimes the "acid" is actually an
312:orbital on the carbon atom with the p
106:The most common oxocarbon anions are
7:
577:correspond to the even less stable
2004:benzoquinonetetraolate; THBQ anion
14:
2671:Hans Meyer; Karl Steiner (1913).
2608:, vol. 94, Issue 2, pp.161–164.
2465:, by Moore, M. H.; Khanna, R. K.
2463:ice: evidence for carbonic acid"
2327:
2232:
2166:
2100:
2037:
1974:
1908:
1852:
1786:
1730:
1664:
1608:
1552:
1490:
1448:
1382:
1295:
1228:
1176:
1131:
1076:
1026:
744:can also be associated with the
277:
272:
195:, whose compounds are usually
1:
2567:10.1016/S1387-3806(98)14208-2
2477:Journal of Physical Chemistry
1004:
175:Stable oxocarbon anions form
2673:"Über ein neues Kohlenoxyd C
2624:"Über ein neues Kohlenoxyd C
2262:benzoquinonetetracarboxylate
1005:
2622:Meyer H, Steiner K (1913).
614:corresponds to the neutral
2781:
2699:10.1002/cber.191304601105
2658:10.1002/cber.191304601105
875:For each oxocarbon anion
772:; namely, the acid minus
2130:ethylenetetracarboxylate
996:List of oxocarbon anions
664:tetrahydroxybenzoquinone
331:with the carbonate ion.
298:molecular orbital theory
179:with a large variety of
2612:accessed on 2009-07-08.
1882:methanetetracarboxylate
900:there are in principle
662:can be reduced to the
484:methanetetracarboxylate
2433:(actually a carbonate
1638:acetylenedicarboxylate
964:, and hydrogenoxalate
498:Every oxocarbon anion
293:
268:of 3 canonical forms.
238:
43:
2632:(A new carbon oxide C
2196:furantetracarboxylate
392:from a corresponding
291:
236:
58:consisting solely of
22:
2588:(25), pp. 8984–8988
207:occurs in the ester
2559:1999IJMSp.188...17S
2516:10.1021/ja01053a065
2489:10.1021/j100843a026
2431:Sodium percarbonate
960:is commonly called
871:Hydrogenated anions
719:An oxocarbon anion
616:cyclopentanepentone
494:Neutralized species
363:An oxocarbon anion
262:valence bond theory
185:interstellar clouds
818:mellitic anhydride
579:1,2-dioxetanedione
294:
239:
91:for some integers
44:
2742:10.1021/ja0643927
2734:J. Am. Chem. Soc.
2594:10.1021/ja9024897
2582:J. Am. Chem. Soc.
2388:
2387:
1478:peroxodicarbonate
1058:(carbonous acid)
944:ranges from 1 to
784:water molecules H
589:; and the stable
466:that would yield
354:Related compounds
193:organic chemistry
2772:
2744:
2731:
2730:
2729:
2721:
2720:
2709:
2703:
2702:
2668:
2662:
2661:
2619:
2613:
2602:
2596:
2577:
2571:
2570:
2526:
2520:
2519:
2504:J. Am. Chem. Soc
2499:
2493:
2492:
2483:(9): 2935–2938.
2472:
2466:
2452:
2410:
2409:
2408:
2400:
2399:
2353:
2352:
2351:
2343:
2342:
2331:
2319:
2318:
2317:
2309:
2308:
2295:
2294:
2293:
2285:
2284:
2276:
2275:
2258:
2257:
2256:
2248:
2247:
2236:
2192:
2191:
2190:
2182:
2181:
2170:
2126:
2125:
2124:
2116:
2115:
2104:
2063:
2062:
2061:
2053:
2052:
2041:
2000:
1999:
1998:
1990:
1989:
1978:
1934:
1933:
1932:
1924:
1923:
1912:
1878:
1877:
1876:
1868:
1867:
1856:
1812:
1811:
1810:
1802:
1801:
1790:
1756:
1755:
1754:
1746:
1745:
1734:
1690:
1689:
1688:
1680:
1679:
1668:
1634:
1633:
1632:
1624:
1623:
1612:
1578:
1577:
1576:
1568:
1567:
1556:
1516:
1515:
1514:
1506:
1505:
1494:
1474:
1473:
1472:
1464:
1463:
1452:
1408:
1407:
1406:
1398:
1397:
1386:
1321:
1320:
1319:
1311:
1310:
1299:
1258:acetylenediolate
1254:
1253:
1252:
1244:
1243:
1232:
1193:
1192:
1191:
1180:
1148:
1147:
1146:
1135:
1093:
1092:
1091:
1080:
1044:
1043:
1042:
1030:
1003:
984:
983:
982:
974:
973:
959:
958:
957:
939:
938:
937:
927:
926:
916:
915:
899:
898:
897:
887:
886:
851:
850:
849:
841:
840:
799:
798:
797:
783:
782:
778:
770:
769:
765:
743:
742:
741:
731:
730:
710:
709:
708:
700:
699:
686:
685:
684:
676:
675:
661:
660:
659:
651:
650:
630:Reduced variants
613:
612:
611:
603:
602:
576:
575:
574:
566:
565:
522:
521:
520:
510:
509:
465:
464:
463:
455:
454:
444:acetylenediolate
425:
424:
423:
387:
386:
385:
375:
374:
349:
348:
347:
281:
276:
266:resonance hybrid
224:
209:dimethyl oxalate
206:
170:
169:
168:
165:
157:
153:
152:
151:
148:
141:
140:
139:
136:
121:
120:
119:
116:
90:
89:
88:
78:
77:
41:
40:
39:
36:
2780:
2779:
2775:
2774:
2773:
2771:
2770:
2769:
2750:
2749:
2748:
2747:
2728:
2725:
2724:
2723:
2719:
2716:
2715:
2714:
2712:
2710:
2706:
2680:
2676:
2670:
2669:
2665:
2639:
2635:
2631:
2627:
2621:
2620:
2616:
2603:
2599:
2578:
2574:
2540:
2534:
2528:
2527:
2523:
2501:
2500:
2496:
2474:
2473:
2469:
2462:
2458:
2453:
2449:
2444:
2417:
2407:
2404:
2403:
2402:
2398:
2395:
2394:
2393:
2391:
2381:
2377:
2369:
2365:
2350:
2347:
2346:
2345:
2341:
2338:
2337:
2336:
2334:
2316:
2313:
2312:
2311:
2307:
2304:
2303:
2302:
2300:
2292:
2289:
2288:
2287:
2283:
2280:
2279:
2278:
2274:
2271:
2270:
2269:
2267:
2255:
2252:
2251:
2250:
2246:
2243:
2242:
2241:
2239:
2224:
2220:
2212:
2208:
2204:
2189:
2186:
2185:
2184:
2180:
2177:
2176:
2175:
2173:
2158:
2154:
2146:
2142:
2138:
2123:
2120:
2119:
2118:
2114:
2111:
2110:
2109:
2107:
2094:
2090:
2079:
2075:
2067:benzenehexolate
2060:
2057:
2056:
2055:
2051:
2048:
2047:
2046:
2044:
2031:
2027:
2016:
2012:
1997:
1994:
1993:
1992:
1988:
1985:
1984:
1983:
1981:
1968:
1964:
1954:
1950:
1946:
1931:
1928:
1927:
1926:
1922:
1919:
1918:
1917:
1915:
1898:
1894:
1890:
1875:
1872:
1871:
1870:
1866:
1863:
1862:
1861:
1859:
1846:
1842:
1832:
1828:
1824:
1809:
1806:
1805:
1804:
1800:
1797:
1796:
1795:
1793:
1776:
1772:
1768:
1753:
1750:
1749:
1748:
1744:
1741:
1740:
1739:
1737:
1724:
1720:
1710:
1706:
1702:
1687:
1684:
1683:
1682:
1678:
1675:
1674:
1673:
1671:
1654:
1650:
1646:
1631:
1628:
1627:
1626:
1622:
1619:
1618:
1617:
1615:
1598:
1594:
1590:
1575:
1572:
1571:
1570:
1566:
1563:
1562:
1561:
1559:
1546:
1542:
1532:
1528:
1513:
1510:
1509:
1508:
1504:
1501:
1500:
1499:
1497:
1471:
1468:
1467:
1466:
1462:
1459:
1458:
1457:
1455:
1440:
1436:
1428:
1424:
1420:
1405:
1402:
1401:
1400:
1396:
1393:
1392:
1391:
1389:
1376:
1372:
1364:
1360:
1353:
1349:
1341:
1337:
1333:
1318:
1315:
1314:
1313:
1309:
1306:
1305:
1304:
1302:
1289:
1285:
1274:
1270:
1266:
1251:
1248:
1247:
1246:
1242:
1239:
1238:
1237:
1235:
1222:
1214:
1205:
1190:
1187:
1186:
1185:
1183:
1170:
1162:
1152:peroxocarbonate
1145:
1142:
1141:
1140:
1138:
1125:
1117:
1109:
1105:
1090:
1087:
1086:
1085:
1083:
1070:
1056:
1041:
1038:
1037:
1036:
1034:
998:
981:
978:
977:
976:
972:
969:
968:
967:
965:
956:
953:
952:
951:
949:
936:
931:
930:
929:
925:
920:
919:
918:
914:
909:
908:
907:
905:
896:
891:
890:
889:
885:
880:
879:
878:
876:
873:
867:
863:
859:
848:
845:
844:
843:
839:
836:
835:
834:
832:
827:
823:
807:
796:
793:
792:
791:
789:
787:
780:
774:
773:
771:
767:
761:
760:
753:
740:
735:
734:
733:
729:
724:
723:
722:
720:
717:
715:Acid anhydrides
707:
704:
703:
702:
698:
695:
694:
693:
691:
689:benzenehexolate
683:
680:
679:
678:
674:
671:
670:
669:
667:
658:
655:
654:
653:
649:
646:
645:
644:
642:
632:
625:
621:
610:
607:
606:
605:
601:
598:
597:
596:
594:
588:
584:
573:
570:
569:
568:
564:
561:
560:
559:
557:
555:
550:carbon trioxide
538:
532:
519:
514:
513:
512:
508:
503:
502:
501:
499:
496:
489:
481:
477:
473:
462:
459:
458:
457:
453:
450:
449:
448:
446:
437:
433:
422:
419:
418:
417:
415:
413:
407:
401:
384:
379:
378:
377:
373:
368:
367:
366:
364:
361:
359:Oxocarbon acids
356:
346:
343:
342:
341:
339:
326:
315:
311:
307:
303:
248:
231:
223:
219:
215:
211:
204:
200:
166:
163:
162:
160:
155:
149:
146:
145:
143:
137:
134:
133:
131:
127:
117:
114:
113:
111:
87:
82:
81:
80:
76:
71:
70:
69:
67:
52:oxocarbon anion
37:
34:
33:
31:
27:
17:
12:
11:
5:
2778:
2776:
2768:
2767:
2762:
2752:
2751:
2746:
2745:
2726:
2717:
2704:
2678:
2674:
2663:
2637:
2633:
2629:
2625:
2614:
2610:Online version
2597:
2572:
2553:(1–2): 17–25.
2536:
2530:
2521:
2494:
2467:
2460:
2456:
2446:
2445:
2443:
2440:
2439:
2438:
2428:
2423:
2416:
2413:
2405:
2396:
2386:
2385:
2383:
2379:
2375:
2371:
2367:
2363:
2359:
2354:
2348:
2339:
2332:
2324:
2323:
2321:
2314:
2305:
2297:
2290:
2281:
2272:
2264:
2259:
2253:
2244:
2237:
2229:
2228:
2226:
2222:
2218:
2214:
2210:
2206:
2202:
2198:
2193:
2187:
2178:
2171:
2163:
2162:
2160:
2156:
2152:
2148:
2144:
2140:
2136:
2132:
2127:
2121:
2112:
2105:
2097:
2096:
2092:
2088:
2084:
2082:
2077:
2073:
2069:
2064:
2058:
2049:
2042:
2034:
2033:
2029:
2025:
2021:
2019:
2014:
2010:
2006:
2001:
1995:
1986:
1979:
1971:
1970:
1966:
1962:
1958:
1956:
1952:
1948:
1944:
1940:
1935:
1929:
1920:
1913:
1905:
1904:
1902:
1900:
1896:
1892:
1888:
1884:
1879:
1873:
1864:
1857:
1849:
1848:
1844:
1840:
1836:
1834:
1830:
1826:
1822:
1818:
1813:
1807:
1798:
1791:
1783:
1782:
1780:
1778:
1774:
1770:
1766:
1762:
1760:dioxosuccinate
1757:
1751:
1742:
1735:
1727:
1726:
1722:
1718:
1714:
1712:
1708:
1704:
1700:
1696:
1691:
1685:
1676:
1669:
1661:
1660:
1658:
1656:
1652:
1648:
1644:
1640:
1635:
1629:
1620:
1613:
1605:
1604:
1602:
1600:
1596:
1592:
1588:
1584:
1579:
1573:
1564:
1557:
1549:
1548:
1544:
1540:
1536:
1534:
1530:
1526:
1522:
1517:
1511:
1502:
1495:
1487:
1486:
1484:
1482:
1480:
1475:
1469:
1460:
1453:
1445:
1444:
1442:
1438:
1434:
1430:
1426:
1422:
1418:
1414:
1409:
1403:
1394:
1387:
1379:
1378:
1374:
1370:
1366:
1362:
1358:
1351:
1347:
1343:
1339:
1335:
1331:
1327:
1322:
1316:
1307:
1300:
1292:
1291:
1287:
1283:
1279:
1277:
1272:
1268:
1264:
1260:
1255:
1249:
1240:
1233:
1225:
1224:
1220:
1216:
1212:
1208:
1203:
1199:
1197:orthocarbonate
1194:
1188:
1181:
1173:
1172:
1168:
1164:
1160:
1156:
1154:
1149:
1143:
1136:
1128:
1127:
1123:
1119:
1115:
1111:
1107:
1103:
1099:
1094:
1088:
1081:
1073:
1072:
1068:
1064:
1059:
1054:
1050:
1045:
1039:
1031:
1023:
1022:
1019:
1016:
1013:
1010:
1007:
997:
994:
979:
970:
954:
932:
921:
910:
892:
881:
872:
869:
865:
861:
857:
846:
837:
825:
821:
805:
802:carbon dioxide
794:
785:
755:
749:
736:
725:
716:
713:
705:
696:
681:
672:
656:
647:
631:
628:
623:
619:
608:
599:
586:
582:
571:
562:
553:
534:
528:
515:
504:
495:
492:
487:
479:
475:
471:
460:
451:
435:
431:
420:
409:
403:
397:
380:
369:
360:
357:
355:
352:
344:
324:
313:
309:
305:
301:
283:
282:
246:
230:
227:
83:
72:
23:2D diagram of
15:
13:
10:
9:
6:
4:
3:
2:
2777:
2766:
2763:
2761:
2758:
2757:
2755:
2743:
2739:
2735:
2708:
2705:
2700:
2696:
2692:
2688:
2687:
2682:
2667:
2664:
2659:
2655:
2651:
2647:
2646:
2641:
2618:
2615:
2611:
2607:
2601:
2598:
2595:
2591:
2587:
2583:
2576:
2573:
2568:
2564:
2560:
2556:
2552:
2548:
2544:
2539:
2533:
2525:
2522:
2517:
2513:
2509:
2505:
2498:
2495:
2490:
2486:
2482:
2478:
2471:
2468:
2464:
2451:
2448:
2441:
2436:
2432:
2429:
2427:
2424:
2422:
2419:
2418:
2414:
2412:
2384:
2382:
2372:
2370:
2360:
2358:
2355:
2333:
2330:
2322:
2320:
2298:
2296:
2265:
2263:
2260:
2238:
2235:
2227:
2225:
2215:
2213:
2199:
2197:
2194:
2172:
2169:
2161:
2159:
2149:
2147:
2133:
2131:
2128:
2106:
2103:
2095:
2085:
2083:
2081:
2070:
2068:
2065:
2043:
2040:
2032:
2022:
2020:
2018:
2007:
2005:
2002:
1980:
1977:
1969:
1959:
1957:
1955:
1941:
1939:
1936:
1914:
1911:
1903:
1901:
1899:
1885:
1883:
1880:
1858:
1855:
1847:
1837:
1835:
1833:
1819:
1817:
1814:
1792:
1789:
1781:
1779:
1777:
1763:
1761:
1758:
1736:
1733:
1725:
1715:
1713:
1711:
1697:
1695:
1692:
1670:
1667:
1659:
1657:
1655:
1641:
1639:
1636:
1614:
1611:
1603:
1601:
1599:
1585:
1583:
1580:
1558:
1555:
1547:
1537:
1535:
1533:
1523:
1521:
1518:
1496:
1493:
1485:
1483:
1481:
1479:
1476:
1454:
1451:
1443:
1441:
1431:
1429:
1415:
1413:
1410:
1388:
1385:
1377:
1367:
1365:
1354:
1344:
1342:
1328:
1326:
1323:
1301:
1298:
1290:
1280:
1278:
1276:
1275:acetylenediol
1261:
1259:
1256:
1234:
1231:
1223:
1217:
1215:
1209:
1207:
1206:methanetetrol
1200:
1198:
1195:
1182:
1179:
1171:
1165:
1163:
1157:
1155:
1153:
1150:
1137:
1134:
1126:
1120:
1118:
1112:
1110:
1100:
1098:
1095:
1082:
1079:
1071:
1065:
1063:
1060:
1057:
1051:
1049:
1046:
1032:
1029:
1020:
1017:
1014:
1011:
1008:
1001:
995:
993:
990:
988:
963:
947:
943:
935:
924:
913:
903:
895:
884:
870:
868:
855:
854:mellitic acid
831:
819:
815:
811:
803:
777:
764:
758:
752:
747:
739:
728:
714:
712:
690:
666:(THBQ) anion
665:
641:
637:
629:
627:
617:
592:
580:
551:
546:
542:
537:
531:
526:
518:
507:
493:
491:
485:
469:
468:acetylenediol
445:
441:
429:
428:carbonic acid
412:
406:
400:
395:
391:
383:
372:
358:
353:
351:
337:
332:
330:
329:isoelectronic
322:
317:
299:
290:
286:
280:
275:
271:
270:
269:
267:
263:
258:
256:
252:
244:
235:
228:
226:
210:
201:[−O−(C=O)
198:
194:
190:
186:
182:
178:
173:
171:
125:
109:
104:
102:
98:
94:
86:
75:
65:
61:
57:
53:
49:
26:
21:
2733:
2707:
2690:
2684:
2666:
2649:
2643:
2617:
2605:
2600:
2585:
2581:
2575:
2550:
2546:
2542:
2537:
2531:
2524:
2510:(25): 7209.
2507:
2503:
2497:
2480:
2476:
2470:
2450:
2389:
2080:benzenehexol
1021:Neutralized
999:
991:
985:is known as
945:
941:
933:
922:
911:
901:
893:
882:
874:
775:
762:
756:
750:
737:
726:
718:
687:and then to
633:
535:
529:
516:
505:
497:
414:. Carbonate
410:
404:
398:
381:
370:
362:
333:
318:
295:
284:
259:
240:
174:
105:
100:
96:
92:
84:
73:
56:negative ion
51:
45:
2693:: 813–815.
2652:: 813–815.
1938:rhodizonate
1412:dicarbonate
962:bicarbonate
640:rhodizonate
527:) variant C
336:carboxylate
327:, which is
321:nitrate ion
243:point group
2765:Oxocarbons
2754:Categories
2442:References
2435:perhydrate
1582:mesoxalate
1018:Anhydride
987:binoxalate
556:; oxalate
251:octet rule
2760:Oxyanions
2545:= 3–6)".
2421:Oxocarbon
2357:mellitate
1816:croconate
1097:carbonate
1048:carbonite
830:mellitate
746:anhydride
591:croconate
541:oxocarbon
255:limestone
216:C−O−(C=O)
108:carbonate
48:chemistry
25:mellitate
2426:Silicate
2415:See also
1694:squarate
1009:Formula
1006:Diagram
940:, where
810:oligomer
525:oxidized
189:moieties
2555:Bibcode
1520:deltate
1325:oxalate
814:polymer
779:⁄
766:⁄
636:reduced
440:alcohol
390:protons
181:cations
124:oxalate
2459:O + CO
2366:(COOH)
593:anion
486:C(COO)
338:group,
197:esters
122:, and
99:, and
64:oxygen
60:carbon
2013:(COH)
1951:(COH)
1529:O(OH)
1202:C(OH)
1053:C(OH)
1015:Acid
1012:Name
828:from
545:oxide
539:, an
304:and p
296:With
260:With
220:−O−CH
177:salts
54:is a
50:, an
2076:(OH)
2017:THBQ
2009:(CO)
1829:(OH)
1707:(OH)
852:via
800:and
394:acid
323:, NO
205:−O−]
154:and
62:and
2738:doi
2695:doi
2654:doi
2590:doi
2586:131
2563:doi
2551:188
2512:doi
2485:doi
950:HCO
812:or
490:).
191:in
46:In
2756::
2691:46
2689:.
2683:.
2675:12
2650:46
2648:.
2642:.
2640:)"
2634:12
2626:12
2584:,
2561:.
2549:.
2508:91
2506:.
2481:73
2479:.
2376:12
2349:12
2340:12
2306:10
2291:10
2273:10
2254:10
2245:10
1355:,
1219:CO
1211:CO
1184:CO
1167:CO
1159:CO
1139:CO
1122:CO
1114:CO
1102:CH
1084:CO
1067:CO
1062:CO
1035:CO
989:.
966:HC
866:12
858:12
847:12
838:12
822:12
804:CO
790:CO
711:.
552:CO
434:CO
416:CO
340:CO
247:3h
225:.
164:4−
161:CO
156:CO
144:CO
135:2−
126:,
115:2−
112:CO
110:,
103:.
95:,
38:12
35:6−
30:12
2740::
2727:6
2722:O
2718:6
2713:C
2701:.
2697::
2681:"
2679:9
2677:O
2660:.
2656::
2638:9
2636:O
2630:9
2628:O
2592::
2569:.
2565::
2557::
2543:n
2541:(
2538:n
2535:O
2532:n
2518:.
2514::
2491:.
2487::
2461:2
2457:2
2437:)
2406:6
2401:O
2397:6
2392:C
2380:9
2378:O
2374:C
2368:6
2364:6
2362:C
2344:O
2335:C
2315:8
2310:O
2301:C
2286:O
2282:4
2277:H
2268:C
2249:O
2240:C
2223:7
2221:O
2219:8
2217:C
2211:9
2209:O
2207:4
2205:H
2203:8
2201:C
2188:9
2183:O
2179:8
2174:C
2157:6
2155:O
2153:6
2151:C
2145:8
2143:O
2141:4
2139:H
2137:6
2135:C
2122:8
2117:O
2113:6
2108:C
2093:6
2091:O
2089:6
2087:C
2078:6
2074:6
2072:C
2059:6
2054:O
2050:6
2045:C
2030:6
2028:O
2026:6
2024:C
2015:4
2011:2
1996:6
1991:O
1987:6
1982:C
1967:6
1965:O
1963:6
1961:C
1953:2
1949:4
1947:O
1945:4
1943:C
1930:6
1925:O
1921:6
1916:C
1897:8
1895:O
1893:4
1891:H
1889:5
1887:C
1874:8
1869:O
1865:5
1860:C
1845:5
1843:O
1841:5
1839:C
1831:2
1827:3
1825:O
1823:5
1821:C
1808:5
1803:O
1799:5
1794:C
1775:6
1773:O
1771:2
1769:H
1767:4
1765:C
1752:6
1747:O
1743:4
1738:C
1723:4
1721:O
1719:4
1717:C
1709:2
1705:2
1703:O
1701:4
1699:C
1686:4
1681:O
1677:4
1672:C
1653:4
1651:O
1649:2
1647:H
1645:4
1643:C
1630:4
1625:O
1621:4
1616:C
1597:5
1595:O
1593:2
1591:H
1589:3
1587:C
1574:5
1569:O
1565:3
1560:C
1545:3
1543:O
1541:3
1539:C
1531:2
1527:3
1525:C
1512:3
1507:O
1503:3
1498:C
1470:6
1465:O
1461:2
1456:C
1439:4
1437:O
1435:2
1433:C
1427:5
1425:O
1423:2
1421:H
1419:2
1417:C
1404:5
1399:O
1395:2
1390:C
1375:4
1373:O
1371:2
1369:C
1363:6
1361:O
1359:4
1357:C
1352:3
1350:O
1348:2
1346:C
1340:4
1338:O
1336:2
1334:H
1332:2
1330:C
1317:4
1312:O
1308:2
1303:C
1288:2
1286:O
1284:2
1282:C
1273:2
1271:O
1269:2
1267:H
1265:2
1263:C
1250:2
1245:O
1241:2
1236:C
1221:4
1213:2
1204:4
1189:4
1169:4
1161:3
1144:4
1124:3
1116:2
1108:3
1106:O
1104:2
1089:3
1069:2
1055:2
1040:2
1033::
980:4
975:O
971:2
955:3
946:n
942:k
934:y
928:O
923:x
917:C
912:k
906:H
902:n
894:y
888:O
883:x
877:C
864:O
862:6
860:H
856:C
842:O
833:C
826:9
824:O
820:C
806:2
795:3
786:2
781:2
776:n
768:2
763:n
759:−
757:y
754:O
751:x
738:y
732:O
727:x
721:C
706:6
701:O
697:6
692:C
682:6
677:O
673:6
668:C
657:6
652:O
648:6
643:C
624:5
622:O
620:5
618:C
609:5
604:O
600:5
595:C
587:4
585:O
583:2
581:C
572:4
567:O
563:2
558:C
554:3
543:(
536:y
533:O
530:x
517:y
511:O
506:x
500:C
488:4
480:2
478:O
476:2
474:H
472:2
470:C
461:2
456:O
452:2
447:C
436:3
432:2
430:H
421:3
411:y
408:O
405:n
402:H
399:x
396:C
382:y
376:O
371:x
365:C
345:2
325:3
314:z
310:z
306:y
302:x
245:D
222:3
218:2
214:3
212:H
203:2
167:4
150:2
147:−
138:4
132:O
130:2
128:C
118:3
101:n
97:y
93:x
85:y
79:O
74:x
68:C
32:O
28:C
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
