212:
320:
304:
288:
332:
134:
27:
731:
702:
185:
orbitals and two on NO, {CoNO}), adopts a bent NO ligand, whereas , with six electrons of pi-symmetry, {FeNO}), adopts a linear nitrosyl. In a further illustration, the {MNO} d-electron count of the anion is shown. In this example, the cyanide ligands are "innocent", i.e., they have a charge of
190:
scheme, Cr has 6 d electrons and NO· has one electron for a total of 7. Two electrons are subtracted to take into account that fragment's overall charge of +2, to give 5. Written in the
Enemark-Feltham notation, the d electron count is {CrNO}. The results are the same if the nitrosyl ligand were
643:
Since nitrogen is more electronegative than carbon, metal-nitrosyl complexes tend to be more electrophilic than related metal carbonyl complexes. Nucleophiles often add to the nitrogen. The nitrogen atom in bent metal nitrosyls is basic, thus can be oxidized, alkylated, and protonated, e.g.:
146:
The M-N-O unit in nitrosyl complexes is usually linear, or no more than 15° from linear. In some complexes, however, especially when back-bonding is less important, the M-N-O angle can strongly deviate from 180°. Linear and bent NO ligands can be distinguished using
181:. In their framework, the factor that determines the bent vs linear NO ligands is the sum of electrons of pi-symmetry. Complexes with "pi-electrons" in excess of 6 tend to have bent NO ligands. Thus, , with eight electrons of pi-symmetry (six in t
1157:
Francine
Agbossou; Edward J. O'Connor; Charles M. Garner; N. Quirós Méndez; Jesús M. Fernández; Alan T. Patton; James A. Ramsden; J. A. Gladysz; Joseph M. O'Connor; Tracy Tajima; Kevin P. Gable (1992). "Cyclopentadienyl Rhenium Complexes".
1439:
Ng, Ho-Yuen; Cheung, Wai-Man; Kwan Huang, Enrique; Wong, Kang-Long; Sung, Herman H.-Y.; Williams, Ian D.; Leung, Wa-Hung (2015). "Ruthenium chalcogenonitrosyl and bridged nitrido complexes containing chelating sulfur and oxygen ligands".
126:. The formal description of nitric oxide as NO does not match certain measureable and calculated properties. In an alternative description, nitric oxide serves as a 3-electron donor, and the metal-nitrogen interaction is a
893:
Ariyarathna, Isuru R.; Miliordos, Evangelos (15 July 2019). "Electronic and geometric structure analysis of neutral and anionic metal nitric chalcogens: The case of MNX series (M=Li, Na, Be and X=O, S, Se, Te)".
2667:
2833:
3020:
2346:
939:"First Principle Studies on Ground and Excited Electronic States: Chemical Bonding in Main-Group Molecules, Molecular Systems with Diffuse Electrons, and Water Activation using Transition Metal Monoxides"
2742:
3104:
2972:
319:
110:
illustrate the analogy between NO and CO. In an electron-counting sense, two linear NO ligands are equivalent to three CO groups. This trend is illustrated by the isoelectronic pair Fe(CO)
151:. Linear M-N-O groups absorb in the range 1650–1900 cm, whereas bent nitrosyls absorb in the range 1525–1690 cm. The differing vibrational frequencies reflect the differing N-O
2672:
2642:
361:
Nitrosyl complexes are traditionally prepared by treating metal complexes with nitric oxide. The method is mainly used with reduced precursors. Illustrative is the nitrosylation of
274:. It consists of a tetrahedron of iron atoms with sulfide ions on three faces of the tetrahedron. Three iron atoms are bonded to two nitrosyl groups. The iron atom on the threefold
746:. In biology and medicine, nitric oxide is however an important signalling molecule in nature and this fact is the basis of the most important applications of metal nitrosyls. The
69:
3241:
3127:
3060:
2927:
3199:
3073:
2990:
2632:
2220:
2887:
3339:
3246:
3179:
3010:
2877:
3140:
3086:
2949:
2936:
3050:
2511:
2995:
2727:
3055:
2657:
2627:
3045:
2647:
1951:
3000:
2652:
2476:
2471:
1988:
3285:
2882:
2622:
2491:
2481:
331:
186:−1 each, −5 total. To balance the fragment's overall charge, the charge on {CrNO} is thus +2 (−3 = −5 + 2). Using the neutral
2897:
2892:
2722:
2164:
1838:
1492:
1291:
Dunn, Peter L.; Cook, Brian J.; Johnson, Samantha I.; Appel, Aaron M.; Bullock, R. Morris (2020). "Oxidation of
Ammonia with Molecular Complexes".
3303:
2213:
2182:
2018:
507:
is a source of nitric oxide complexes, although the details are obscure. Probably relevant is the conventional self-dehydration of nitric acid:
727:
from internal combustion engines. This application has been described as "one of the most successful stories in the development of catalysts."
2321:
2187:
2055:
3040:
3025:
2803:
2783:
2752:
2326:
2306:
2301:
2296:
3308:
3099:
3030:
2778:
2757:
1342:
Walker, F. A. (2005). "Nitric Oxide
Interaction with Insect Nitrophorins and Thoughts on the Electron Configuration of the FeNO Complex".
303:
174:-. The NO is also common for alkali-metal or alkaline-earth metal-NO molecules. For example. LiNO and BeNO bear LiNO and BeNO ionic form.
3353:
3184:
2917:
2311:
2291:
1224:
James K. Hoyano; Peter
Legzdins; John T. Malito (1978). "(η ‐Cyclopentadienydnitrosyl Complexes of Chromium, Molybdenum, and Jungsten".
3219:
3214:
2828:
2823:
2747:
2442:
2437:
2432:
2427:
2206:
2074:
287:
256:
sharing an edge. Each iron atom is bonded linearly to two NO ligands and shares two bridging sulfidi ligands with the other iron atom.
3209:
3204:
3194:
3174:
2907:
2422:
2145:
1869:
166:
The bent NO ligand is sometimes described as the anion, NO. Prototypes for such compounds are the organic nitroso compounds, such as
2818:
2732:
2683:
1091:
Paul
Gilmont; Arthur A. Blanchard (1946). "Dicobalt Octacarbonyl, Cobalt Nitrosyl Tricarbonyl, and Cobalt Tetracarbomyl Hydride".
223:
ligands are known where the NO is coordinated by its oxygen atom. They can be generated by UV-irradiation of nitrosyl complexes.
3005:
2617:
1805:
236:
Metal complexes containing only nitrosyl ligands are called isoleptic nitrosyls. They are rare, the premier member being Cr(NO)
2737:
2010:
1377:
Kaspar, Jan; Fornasiero, Paolo; Hickey, Neal (2003). "Automotive
Catalytic Converters: Current Status and Some Perspectives".
1818:
1689:
1275:
1241:
1208:
1175:
1141:
1108:
1075:
877:
627:
This equilibrium serves to confirm that the linear nitrosyl ligand is, formally, NO, with nitrogen in the oxidation state +3
2124:
1975:
1896:
1843:
1485:
1404:
Jessica
Fitzpatrick; Eunsuk Kim (2015). "Synthetic Modeling Chemistry of Iron–Sulfur Clusters in Nitric Oxide Signaling".
2982:
1861:
1813:
955:
Enemark, J. H.; Feltham, R. D. (1974). "Principles of structure, bonding, and reactivity for metal nitrosyl complexes".
80:
Most complexes containing the NO ligand can be viewed as derivatives of the nitrosyl cation, NO. The nitrosyl cation is
3408:
2136:
2091:
2047:
2031:
1833:
1800:
1790:
1677:
778:
Several complexes are known with NS ligands. Like nitrosyls, thionitrosyls exist as both linear and bent geometries.
2177:
2086:
1943:
1742:
823:
Hayton, T. W.; Legzdins, P.; Sharp, W. B. (2002). "Coordination and
Organometallic Chemistry of Metal-NO Complexes".
2039:
2002:
1997:
1963:
1754:
1719:
1702:
1694:
1630:
1570:
602:
983:
3545:
2637:
1848:
1621:
1609:
1580:
1575:
1478:
705:
Nitrosylation of a heme-thiolate, steps in cell signaling by nitric oxide (porphyrin is depicted as the square).
3422:
1924:
1828:
1782:
1665:
1585:
1539:
750:
anion, , a mixed nitrosyl cyano complex, has pharmaceutical applications as a slow release agent for NO. The
1597:
215:
Structure of the isonitrosyl complex (color code: red (O), blue (N), gray (C), dark green (Ru), green (Cl)).
1191:
3510:
2496:
2116:
1938:
1652:
92:. The nitrosyl cation serves as a two-electron donor to the metal and accepts electrons from the metal via
3540:
3535:
3358:
3169:
2382:
366:
97:
1156:
88:, thus the bonding between a nitrosyl ligand and a metal follows the same principles as the bonding in
2506:
556:
Some anionic nitrito complexes undergo acid-induced deoxygenation to give the linear nitrosyl complex.
407:
1124:
Richard R. Thomas; Ayusman Sen (1990). "Acetonitrile Complexes of Selected Transition Metal Cations".
252:, which is a sodium salt of the anion . The structure of the anion can be viewed as consisting of two
2392:
2280:
211:
2100:
1660:
1515:
715:
203:. In the compound , three NO groups bridge two metal centres and one NO group bridge to all three.
3439:
2967:
2699:
2387:
1888:
767:
735:
310:
257:
3436:
2397:
1983:
984:"Room‐Temperature Photogeneration of Nitrosyl Linkage Isomers in Ruthenium Nitrosyl Complexes"
33:, a medicinally significant metal nitrosyl-pentacyanoferrate (Fe-III) compound, used to treat
3363:
2860:
2704:
1823:
1067:
869:
353:
Many nitrosyl complexes are quite stable, thus many methods can be used for their synthesis.
294:
271:
249:
148:
794:
2709:
2662:
2486:
2412:
2402:
1774:
1501:
573:
30:
8:
3373:
763:
45:
2604:
2561:
2235:
2169:
1915:
1520:
1324:
1014:
919:
240:. Even trinitrosyl complexes are uncommon, whereas polycarbonyl complexes are routine.
133:
1390:
982:
Mikhailov, Artem A.; Wenger, Emmanuel; Kostin, Gennadiy A.; Schaniel, Dominik (2019).
968:
2581:
2271:
1457:
1421:
1359:
1328:
1316:
1308:
1271:
1237:
1204:
1171:
1137:
1104:
1071:
1018:
1006:
911:
873:
840:
743:
441:
187:
2198:
1355:
923:
3255:
2849:
2576:
2527:
2407:
1449:
1413:
1386:
1351:
1300:
1257:
1229:
1196:
1163:
1129:
1096:
1059:
1041:
998:
964:
903:
861:
832:
672:
123:
89:
53:
325:
The nitroprusside anion, , an octahedral complex containing a "linear NO" ligand.
3530:
3443:
3114:
2902:
2501:
1417:
1261:
410:. This reagent has been applied to the hexacarbonyls of molybdenum and tungsten:
362:
200:
104:
85:
73:
56:. Many kinds of nitrosyl complexes are known, which vary both in structure and co
3463:
3122:
3015:
2912:
2612:
2599:
2586:
2232:
1933:
1647:
1267:
1233:
1200:
1167:
1133:
1100:
751:
167:
20:
3524:
3404:
3153:
2962:
2591:
2571:
2566:
2551:
1642:
1547:
759:
747:
532:
460:
275:
261:
119:
81:
938:
3481:
3457:
2788:
2556:
2256:
2243:
2229:
1461:
1425:
1363:
1320:
1223:
1045:
1010:
1002:
915:
844:
536:
93:
49:
34:
3487:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
26:
3494:
3265:
3189:
2798:
2793:
2678:
2519:
2417:
2261:
1707:
1470:
1304:
504:
253:
160:
156:
127:
1376:
406:
Replacement of ligands by the nitrosyl cation may be accomplished using
248:
One of the earliest examples of a nitrosyl complex to be synthesized is
3467:
3447:
3381:
3035:
2452:
2447:
2336:
2316:
1453:
152:
1312:
907:
836:
3453:
3412:
3275:
3270:
2331:
3474:
3430:
3416:
3331:
3233:
2922:
2813:
2360:
2251:
3394:
3260:
2773:
2768:
2717:
2536:
2531:
2457:
2377:
2366:
730:
449:
177:
The adoption of linear vs bent bonding can be analyzed with the
3490:
3386:
3280:
2843:
1090:
68:
57:
1190:
822:
701:
264:
structure. The anion in this species has the formula . It has
1403:
981:
601:
An important reaction is the acid/base equilibrium, yielding
1123:
463:
is a source of nitric oxide anion via a disproportionation:
3368:
3295:
2869:
755:
16:
Complex of a transition metal bonded to nitric oxide: Me–NO
278:
has a single nitrosyl group which also lies on that axis.
742:
Metal-catalyzed reactions of NO are not often useful in
340:-, an octahedral complex containing a "bent NO" ligand.
2252:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
1438:
226:
2228:
1290:
892:
2743:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
801:. The American Society of Health-System Pharmacists
754:function of NO is effected via its complexation to
714:Metal-nitrosyls are assumed to be intermediates in
1034:Angewandte Chemie International Edition in English
576:, the ammonia ligand can be oxidized to nitrosyl:
219:Usually only of transient existence, complexes of
141:
2557:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
1256:
1058:
1032:Herberhold Max (1972). "Tetranitrosylchromium ".
950:
948:
860:
3522:
567:
231:
2418:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
668:In rare cases, NO is cleaved by metal centers:
1031:
954:
945:
243:
2834:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
2393:Ethylene glycol dinitrate (EGDN; nitroglycol)
2214:
1486:
1341:
531:Nitric acid is used in some preparations of
194:
936:
2221:
2207:
1500:
1493:
1479:
818:
816:
564:The reaction is reversible in some cases.
444:and molybdenum hexacarbonyl react to give
76:. (Middle) Sigma bond. (Bottom) Back-bond.
2577:Isobutyl nitrite (2-methylpropyl nitrite)
2487:Nitroglycerin (glyceryl trinitrate (GTN))
1293:Journal of the American Chemical Society
729:
700:
210:
132:
67:
63:
25:
2653:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
2643:S-Nitroso-N-valerylpenicillamine (SNVP)
813:
3523:
2638:S-Nitroso-N-acetylpenicillamine (SNAP)
2512:Sodium trioxodinitrate (Angeli's salt)
206:
2202:
1474:
455:
170:. A complex with a bent NO ligand is
3473:non-selective PDE inhibitors (e.g.,
2257:Nitric oxide (NO; nitrogen monoxide)
551:
401:
2497:Pentaerithrityl tetranitrate (PETN)
2383:Diethylene glycol dinitrate (DEGDN)
1335:
1284:
937:Ariyarathna, Isuru (1 March 2021).
856:
854:
499:
227:Representative classes of compounds
13:
3402:Indirect/downstream NO modulators:
3170:Asymmetric dimethylarginine (ADMA)
2279:
1228:. Vol. 13. pp. 126–131.
1195:. Vol. 12. pp. 264–266.
1162:. Vol. 29. pp. 211–225.
896:Journal of Computational Chemistry
603:transition metal nitrite complexes
14:
3557:
3200:Nitroarginine methyl ester (NAME)
2663:S-Nitrosoglutathione (GSNO, SNOG)
2633:S-Nitroso-N-acetylcysteine (SNAC)
2507:Propylene glycol dinitrate (PGDN)
2262:Nitrosonium (NO; nitrosyl cation)
199:Nitric oxide can also serve as a
122:and, incidentally, both obey the
1128:. Vol. 28. pp. 63–67.
851:
773:
758:proteins, where it binds in the
330:
318:
302:
286:
2728:Diethylenetriamine/NO (DETA/NO)
1432:
1397:
1370:
1356:10.1016/j.jinorgbio.2004.10.009
1250:
1217:
1184:
1150:
1117:
1084:
718:, which reduce the emission of
709:
142:Linear vs bent nitrosyl ligands
2928:N-(1-Iminoethyl)-L-ornithine (
1052:
1025:
991:Chemistry – A European Journal
975:
930:
886:
787:
452:is also used as an NO source.
348:
1:
3511:Receptor/signaling modulators
3180:Guanidinoethyldisulfide (GED)
2398:Isosorbide mononitrate (ISMN)
2388:Erythritol tetranitrate (ETN)
1391:10.1016/S0920-5861(02)00384-X
969:10.1016/S0010-8545(00)80259-3
781:
568:Oxidation of ammine complexes
232:Homoleptic nitrosyl complexes
2648:S-Nitrosocaptopril (SNO-Cap)
2477:Nitroflurbiprofen (HCT-1026)
2472:Nitroatorvastatin (NCX-6560)
1418:10.1021/acs.accounts.5b00246
1095:. Vol. 2. p. 238.
762:. Nitric oxide also attacks
596:
7:
3123:Aminoguanidine (pimagedine)
3016:Aminoguanidine (pimagedine)
2913:Aminoguanidine (pimagedine)
2677:N-Nitroso compounds (e.g.,
2492:Nitropravastatin (NCX-6550)
2403:Isosorbide dinitrate (ISDN)
367:cobalt tricarbonyl nitrosyl
244:Roussin red and black salts
72:(Top) the HOMO and LUMO of
10:
3562:
3409:AT-II receptor antagonists
3154:Nitroarginine (NNA, NOARG)
2991:1-Amino-2-hydroxyguanidine
2963:Nitroarginine (NNA, NOARG)
2710:Sodium nitroprusside (SNP)
1234:10.1002/9780470132494.ch21
1201:10.1002/9780470132432.ch47
1168:10.1002/9780470132609.ch51
1134:10.1002/9780470132593.ch14
1101:10.1002/9780470132333.ch76
408:nitrosyl tetrafluoroborate
356:
137:linear and bent M-NO bonds
118:and . These complexes are
18:
3504:
3321:
3294:
3232:
3162:
3113:
2981:
2868:
2859:
2842:
2359:
2270:
2242:
2157:
2067:
1908:
1881:
1767:
1735:
1563:
1532:
1508:
1263:Chemistry of the Elements
1260:; Earnshaw, Alan (1984).
1064:Chemistry of the Elements
1062:; Earnshaw, Alan (1997).
866:Chemistry of the Elements
864:; Earnshaw, Alan (1997).
768:dinitrosyl iron complexes
195:Bridging nitrosyl ligands
2888:3-Chloro-5-nitroindazole
2723:Diethylamine/NO (DEA/NO)
2695:Metal nitrosyl complexes
2623:S-Nitrosoalbumin (SNALB)
2317:Cinaciguat (BAY 58-2667)
179:Enemark-Feltham notation
42:Metal nitrosyl complexes
19:Not to be confused with
3480:PDE9 inhibitors (e.g.,
2968:Pentamidine isethionate
2878:3-Bromo-7-nitroindazole
2765:Heterocyclic compounds:
2289:Activators/stimulators:
736:dinitrosyl iron complex
3546:Coordination chemistry
3437:L-Type calcium channel
1502:Coordination complexes
1046:10.1002/anie.197210921
1003:10.1002/chem.201901205
795:"Sodium Nitroprusside"
739:
706:
656:(CO)ClOsNO + HCl → (Ph
574:metal-ammine complexes
216:
138:
77:
38:
3041:Cindunistat (SD-6010)
2996:2-Ethylaminoguanidine
2753:Spermine/NO (SPER/NO)
2550:O-Nitroso compounds (
1068:Butterworth-Heinemann
1060:Greenwood, Norman N.
870:Butterworth-Heinemann
862:Greenwood, Norman N.
733:
704:
214:
191:considered NO or NO.
149:infrared spectroscopy
136:
71:
64:Bonding and structure
29:
3427:receptor antagonists
3100:Ronopterin (VAS-203)
2799:Molsidomine (SIN-10)
2720:(diazeniumdiolates):
2700:Roussin's black salt
2413:Mannitol hexanitrate
1305:10.1021/jacs.0c08269
1258:Greenwood, Norman N.
872:. pp. 447–453.
764:iron-sulfur proteins
716:catalytic converters
311:Roussin's black salt
258:Roussin's black salt
31:Sodium nitroprusside
2794:Linsidomine (SIN-1)
2691:Nitrosyl compounds:
2658:S-Nitrosodiclofenac
2628:S-Nitrosated AR545C
2613:S-Nitroso compounds
1448:(42): 18459–18468.
1442:Dalton Transactions
1299:(42): 17845–17858.
1226:Inorganic Syntheses
1193:Inorganic Syntheses
1160:Inorganic Syntheses
1126:Inorganic Syntheses
1093:Inorganic Syntheses
693:(Me)Nb(O)NMe → 2 Cp
260:has a more complex
207:Isonitrosyl ligands
3541:Nitrosyl complexes
3536:Nitrogen compounds
2705:Roussin's red salt
2562:Cyclohexyl nitrite
2453:Nipradilol (K-351)
1454:10.1039/C5DT02513C
740:
707:
697:Nb(O)Me + ½MeN=NMe
456:From hydroxylamine
295:Roussin's red salt
250:Roussin's red salt
217:
139:
90:carbonyl complexes
78:
52:, NO, bonded to a
39:
3518:
3517:
3343:
3334:
3317:
3316:
3250:
3228:
3227:
3148:
3144:
3135:
3131:
3128:N-(1-Iminoethyl)-
3094:
3090:
3081:
3077:
3074:N-(1-Iminoethyl)-
3068:
3064:
3061:N-(1-Iminoethyl)-
3001:2-Iminopiperidine
2957:
2953:
2944:
2940:
2931:
2853:
2582:Isopropyl nitrite
2528:Nitroso compounds
2370:
2355:
2354:
2196:
2195:
1344:J. Inorg. Biochem
1277:978-0-08-022057-4
1243:978-0-470-13249-4
1210:978-0-470-13243-2
1177:978-0-470-13260-9
1143:978-0-470-13259-3
1110:978-0-470-13233-3
1077:978-0-08-037941-8
1040:(12): 1092–1094.
997:(31): 7569–7574.
908:10.1002/jcc.25829
902:(19): 1740–1751.
879:978-0-08-037941-8
837:10.1021/cr000074t
744:organic chemistry
552:From nitrous acid
442:Nitrosyl chloride
188:electron counting
3553:
3444:dihydropyridines
3344:-arginine (NOHA)
3341:
3332:
3286:alpha aminoacids
3256:chlorogenic acid
3251:-arginine (NOHA)
3248:
3146:
3142:
3133:
3129:
3092:
3088:
3079:
3075:
3066:
3062:
2955:
2951:
2942:
2938:
2929:
2883:3-Chloroindazole
2866:
2865:
2857:
2856:
2847:
2545:
2544:
2482:Nitrofluvastatin
2466:
2465:
2408:Itramin tosilate
2364:
2277:
2276:
2223:
2216:
2209:
2200:
2199:
1495:
1488:
1481:
1472:
1471:
1466:
1465:
1436:
1430:
1429:
1412:(8): 2453–2461.
1401:
1395:
1394:
1374:
1368:
1367:
1339:
1333:
1332:
1288:
1282:
1281:
1254:
1248:
1247:
1221:
1215:
1214:
1188:
1182:
1181:
1154:
1148:
1147:
1121:
1115:
1114:
1088:
1082:
1081:
1066:(2nd ed.).
1056:
1050:
1049:
1029:
1023:
1022:
988:
979:
973:
972:
957:Coord. Chem. Rev
952:
943:
942:
934:
928:
927:
890:
884:
883:
868:(2nd ed.).
858:
849:
848:
820:
811:
810:
808:
806:
791:
726:
591:
587:
547:+ → + OH + OCN
500:From nitric acid
490:
474:
425:
421:
402:From NO and NOCl
396:
388:
384:
334:
322:
306:
290:
124:18-electron rule
96:. The compounds
54:transition metal
3561:
3560:
3556:
3555:
3554:
3552:
3551:
3550:
3521:
3520:
3519:
3514:
3500:
3464:PDE5 inhibitors
3426:
3390:
3377:
3313:
3290:
3224:
3158:
3109:
2977:
2903:7-Nitroindazole
2898:6-Nitroindazole
2893:5-Nitroindazole
2846:
2838:
2615:(thionitrites):
2543:
2540:
2539:
2538:
2502:Propatylnitrate
2464:
2461:
2460:
2459:
2363:
2351:
2266:
2238:
2227:
2197:
2192:
2173:
2153:
2140:
2132:
2128:
2120:
2112:
2108:
2104:
2095:
2082:
2078:
2063:
2059:
2051:
2043:
2035:
2026:
2022:
2014:
2006:
1992:
1979:
1971:
1967:
1959:
1955:
1947:
1928:
1919:
1904:
1900:
1892:
1877:
1865:
1856:
1852:
1809:
1786:
1778:
1763:
1758:
1750:
1746:
1731:
1727:
1723:
1715:
1711:
1698:
1685:
1681:
1673:
1669:
1656:
1638:
1634:
1625:
1617:
1613:
1605:
1601:
1593:
1589:
1559:
1555:
1551:
1543:
1528:
1524:
1504:
1499:
1469:
1437:
1433:
1402:
1398:
1379:Catalysis Today
1375:
1371:
1340:
1336:
1289:
1285:
1278:
1270:. p. 516.
1255:
1251:
1244:
1222:
1218:
1211:
1189:
1185:
1178:
1155:
1151:
1144:
1122:
1118:
1111:
1089:
1085:
1078:
1070:. p. 449.
1057:
1053:
1030:
1026:
986:
980:
976:
963:(13): 339–406.
953:
946:
935:
931:
891:
887:
880:
859:
852:
821:
814:
804:
802:
793:
792:
788:
784:
776:
734:Structure of a
725:
719:
712:
696:
692:
685:
681:
677:
663:
659:
655:
651:
638:
634:
622:
618:
614:
599:
589:
585:
583:
570:
554:
546:
526:
522:
518:
514:
502:
494:
488:
486:
482:
478:
472:
470:
458:
447:
437:
433:
429:
423:
419:
417:
404:
394:
392:
386:
382:
380:
376:
363:cobalt carbonyl
359:
351:
346:
345:
344:
341:
335:
326:
323:
314:
307:
298:
291:
270:
246:
239:
234:
229:
209:
201:bridging ligand
197:
184:
159:) and bent NO (
144:
117:
113:
108:
101:
86:carbon monoxide
66:
24:
17:
12:
11:
5:
3559:
3549:
3548:
3543:
3538:
3533:
3516:
3515:
3505:
3502:
3501:
3499:
3498:
3488:
3485:
3478:
3471:
3461:
3451:
3434:
3424:
3420:
3405:ACE inhibitors
3398:
3397:
3392:
3388:
3384:
3379:
3375:
3371:
3366:
3361:
3356:
3347:
3346:
3337:
3325:
3323:
3319:
3318:
3315:
3314:
3312:
3311:
3306:
3300:
3298:
3292:
3291:
3289:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3244:
3238:
3236:
3230:
3229:
3226:
3225:
3223:
3222:
3217:
3212:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3166:
3164:
3160:
3159:
3157:
3156:
3151:
3138:
3125:
3119:
3117:
3111:
3110:
3108:
3107:
3102:
3097:
3084:
3071:
3058:
3053:
3048:
3043:
3038:
3033:
3028:
3023:
3018:
3013:
3008:
3003:
2998:
2993:
2987:
2985:
2979:
2978:
2976:
2975:
2970:
2965:
2960:
2947:
2934:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2874:
2872:
2863:
2854:
2840:
2839:
2837:
2836:
2831:
2826:
2821:
2816:
2807:
2806:
2801:
2796:
2791:
2776:
2761:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2713:
2712:
2707:
2702:
2687:
2686:
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2608:-Butyl nitrite
2602:
2600:Pentyl nitrite
2597:
2595:-Butyl nitrite
2589:
2587:Methyl nitrite
2584:
2579:
2574:
2569:
2564:
2559:
2552:alkyl nitrites
2541:
2523:
2522:
2517:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2462:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2373:
2371:
2357:
2356:
2353:
2352:
2350:
2349:
2340:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2285:
2283:
2274:
2268:
2267:
2265:
2264:
2259:
2254:
2248:
2246:
2240:
2239:
2226:
2225:
2218:
2211:
2203:
2194:
2193:
2191:
2190:
2185:
2180:
2175:
2171:
2167:
2161:
2159:
2158:Halide donors:
2155:
2154:
2152:
2151:
2143:
2138:
2134:
2130:
2126:
2122:
2118:
2114:
2110:
2106:
2102:
2098:
2093:
2089:
2084:
2080:
2076:
2071:
2069:
2065:
2064:
2062:
2061:
2057:
2053:
2049:
2045:
2041:
2037:
2033:
2029:
2024:
2020:
2016:
2012:
2008:
2004:
2000:
1995:
1990:
1986:
1981:
1977:
1973:
1969:
1965:
1961:
1957:
1953:
1949:
1945:
1941:
1936:
1931:
1926:
1922:
1917:
1912:
1910:
1906:
1905:
1903:
1902:
1898:
1894:
1890:
1885:
1883:
1879:
1878:
1876:
1875:
1867:
1863:
1859:
1854:
1850:
1846:
1841:
1836:
1831:
1826:
1821:
1816:
1811:
1807:
1803:
1798:
1793:
1788:
1784:
1780:
1776:
1771:
1769:
1765:
1764:
1762:
1761:
1756:
1752:
1748:
1744:
1739:
1737:
1733:
1732:
1730:
1729:
1725:
1721:
1717:
1713:
1709:
1705:
1700:
1696:
1692:
1687:
1683:
1679:
1675:
1671:
1667:
1663:
1658:
1654:
1650:
1645:
1640:
1636:
1632:
1628:
1623:
1619:
1615:
1611:
1607:
1603:
1599:
1595:
1591:
1587:
1583:
1578:
1573:
1567:
1565:
1561:
1560:
1558:
1557:
1553:
1549:
1545:
1541:
1536:
1534:
1530:
1529:
1527:
1526:
1522:
1518:
1512:
1510:
1506:
1505:
1498:
1497:
1490:
1483:
1475:
1468:
1467:
1431:
1406:Acc. Chem. Res
1396:
1385:(4): 419–449.
1369:
1350:(1): 216–236.
1334:
1283:
1276:
1268:Pergamon Press
1249:
1242:
1216:
1209:
1183:
1176:
1149:
1142:
1116:
1109:
1083:
1076:
1051:
1024:
974:
944:
929:
885:
878:
850:
831:(1): 935–991.
812:
785:
783:
780:
775:
772:
721:
711:
708:
699:
698:
694:
690:
687:
683:
679:
675:
666:
665:
661:
657:
653:
649:
641:
640:
636:
632:
631:NO + 2 OH ⇌ NO
625:
624:
620:
616:
610:
598:
595:
594:
593:
581:
569:
566:
562:
561:
553:
550:
549:
548:
544:
529:
528:
524:
520:
516:
512:
501:
498:
497:
496:
492:
484:
480:
476:
468:
457:
454:
445:
439:
438:
435:
431:
427:
415:
403:
400:
399:
398:
390:
378:
374:
358:
355:
350:
347:
343:
342:
336:
329:
327:
324:
317:
315:
308:
301:
299:
292:
285:
282:
281:
280:
268:
245:
242:
237:
233:
230:
228:
225:
208:
205:
196:
193:
182:
168:nitrosobenzene
143:
140:
115:
111:
106:
99:
65:
62:
21:Nitro compound
15:
9:
6:
4:
3:
2:
3558:
3547:
3544:
3542:
3539:
3537:
3534:
3532:
3529:
3528:
3526:
3513:
3512:
3509:
3503:
3496:
3492:
3489:
3486:
3483:
3479:
3476:
3472:
3469:
3465:
3462:
3459:
3455:
3452:
3449:
3445:
3441:
3438:
3435:
3432:
3428:
3421:
3418:
3414:
3410:
3406:
3403:
3400:
3399:
3396:
3393:
3391:
3385:
3383:
3380:
3378:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3349:
3348:
3345:
3338:
3336:
3330:
3327:
3326:
3324:
3320:
3310:
3307:
3305:
3304:Calmidazolium
3302:
3301:
3299:
3297:
3293:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3245:
3243:
3240:
3239:
3237:
3235:
3231:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3167:
3165:
3161:
3155:
3152:
3150:
3139:
3137:
3126:
3124:
3121:
3120:
3118:
3116:
3112:
3106:
3103:
3101:
3098:
3096:
3085:
3083:
3072:
3070:
3059:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3022:
3019:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2988:
2986:
2984:
2980:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2948:
2946:
2935:
2933:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2875:
2873:
2871:
2867:
2864:
2862:
2858:
2855:
2851:
2845:
2841:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2809:
2808:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2780:
2777:
2775:
2772:
2770:
2766:
2763:
2762:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2719:
2715:
2714:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2692:
2689:
2688:
2685:
2682:
2680:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2609:
2607:
2603:
2601:
2598:
2596:
2594:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2572:Hexyl nitrite
2570:
2568:
2567:Ethyl nitrite
2565:
2563:
2560:
2558:
2555:
2553:
2547:
2535:
2533:
2529:
2525:
2524:
2521:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2375:
2374:
2372:
2368:
2362:
2358:
2348:
2345:
2342:
2341:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2287:
2286:
2284:
2282:
2278:
2275:
2273:
2269:
2263:
2260:
2258:
2255:
2253:
2250:
2249:
2247:
2245:
2241:
2237:
2234:
2231:
2224:
2219:
2217:
2212:
2210:
2205:
2204:
2201:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2168:
2166:
2163:
2162:
2160:
2156:
2150:
2149:
2144:
2142:
2135:
2133:
2123:
2121:
2115:
2113:
2099:
2097:
2090:
2088:
2085:
2083:
2073:
2072:
2070:
2066:
2060:
2054:
2052:
2046:
2044:
2038:
2036:
2030:
2028:
2017:
2015:
2009:
2007:
2001:
1999:
1996:
1994:
1987:
1985:
1982:
1980:
1974:
1972:
1962:
1960:
1950:
1948:
1942:
1940:
1937:
1935:
1932:
1930:
1923:
1921:
1914:
1913:
1911:
1907:
1901:
1895:
1893:
1887:
1886:
1884:
1880:
1874:
1872:
1868:
1866:
1860:
1858:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1810:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1781:
1779:
1773:
1772:
1770:
1766:
1760:
1753:
1751:
1741:
1740:
1738:
1734:
1728:
1718:
1716:
1706:
1704:
1701:
1699:
1693:
1691:
1688:
1686:
1676:
1674:
1664:
1662:
1659:
1657:
1651:
1649:
1646:
1644:
1641:
1639:
1629:
1627:
1620:
1618:
1608:
1606:
1596:
1594:
1584:
1582:
1579:
1577:
1574:
1572:
1569:
1568:
1566:
1562:
1556:
1546:
1544:
1538:
1537:
1535:
1531:
1525:
1519:
1517:
1514:
1513:
1511:
1507:
1503:
1496:
1491:
1489:
1484:
1482:
1477:
1476:
1473:
1463:
1459:
1455:
1451:
1447:
1443:
1435:
1427:
1423:
1419:
1415:
1411:
1407:
1400:
1392:
1388:
1384:
1380:
1373:
1365:
1361:
1357:
1353:
1349:
1345:
1338:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1294:
1287:
1279:
1273:
1269:
1265:
1264:
1259:
1253:
1245:
1239:
1235:
1231:
1227:
1220:
1212:
1206:
1202:
1198:
1194:
1187:
1179:
1173:
1169:
1165:
1161:
1153:
1145:
1139:
1135:
1131:
1127:
1120:
1112:
1106:
1102:
1098:
1094:
1087:
1079:
1073:
1069:
1065:
1061:
1055:
1047:
1043:
1039:
1035:
1028:
1020:
1016:
1012:
1008:
1004:
1000:
996:
992:
985:
978:
970:
966:
962:
958:
951:
949:
940:
933:
925:
921:
917:
913:
909:
905:
901:
897:
889:
881:
875:
871:
867:
863:
857:
855:
846:
842:
838:
834:
830:
826:
819:
817:
800:
799:www.drugs.com
796:
790:
786:
779:
774:Thionitrosyls
771:
769:
765:
761:
760:bent geometry
757:
753:
749:
748:nitroprusside
745:
737:
732:
728:
724:
717:
703:
688:
674:
671:
670:
669:
664:(CO)ClOsN(H)O
647:
646:
645:
630:
629:
628:
613:
608:
607:
606:
604:
579:
578:
577:
575:
565:
559:
558:
557:
542:
541:
540:
538:
534:
533:nitroprusside
510:
509:
508:
506:
466:
465:
464:
462:
461:Hydroxylamine
453:
451:
443:
413:
412:
411:
409:
372:
371:
370:
368:
364:
354:
339:
333:
328:
321:
316:
312:
309:The anion in
305:
300:
296:
293:The anion in
289:
284:
283:
279:
277:
276:symmetry axis
273:
267:
263:
259:
255:
251:
241:
224:
222:
213:
204:
202:
192:
189:
180:
175:
173:
169:
164:
162:
158:
154:
150:
135:
131:
129:
125:
121:
120:isoelectronic
109:
102:
95:
91:
87:
83:
82:isoelectronic
75:
70:
61:
59:
55:
51:
48:that contain
47:
43:
36:
32:
28:
22:
3507:
3506:
3482:paraxanthine
3458:beta blocker
3401:
3350:
3328:
3132:-ornithine (
3065:-ornithine (
2810:
2789:Feprosidnine
2784:Sydnonimines
2782:
2767:
2764:
2716:
2694:
2693:
2690:
2679:nitrosamines
2676:
2611:
2605:
2592:
2549:
2526:
2376:
2343:
2322:GSK-2181236A
2288:
2230:Nitric oxide
2147:
1870:
1795:
1445:
1441:
1434:
1409:
1405:
1399:
1382:
1378:
1372:
1347:
1343:
1337:
1296:
1292:
1286:
1262:
1252:
1225:
1219:
1192:
1186:
1159:
1152:
1125:
1119:
1092:
1086:
1063:
1054:
1037:
1033:
1027:
994:
990:
977:
960:
956:
932:
899:
895:
888:
865:
828:
824:
803:. Retrieved
798:
789:
777:
741:
722:
713:
710:Applications
686:(Me)Nb(O)NMe
667:
642:
626:
611:
600:
571:
563:
555:
537:ferrocyanide
530:
503:
479:OH + KOH → K
459:
440:
405:
360:
352:
337:
265:
247:
235:
220:
218:
198:
178:
176:
171:
165:
155:for linear (
145:
94:back-bonding
79:
50:nitric oxide
41:
40:
35:hypertension
3495:simvastatin
3329:Precursors:
3266:epicatechin
3190:Indospicine
3145:-arginine (
3091:-arginine (
3026:AR-C 102222
2954:-arginine (
2941:-arginine (
2804:Sydnonimine
2537:Nitrite (NO
2520:Trolnitrate
2516:Tenitramine
2458:Nitrate (NO
2344:Inhibitors:
2327:Praliciguat
2307:BAY 60-4552
2302:BAY 41-8543
2297:BAY 41-2272
584:O + → + 5
560:+ H → + OH
505:Nitric acid
349:Preparation
221:isonitrosyl
161:double bond
157:triple bond
153:bond orders
128:triple bond
3525:Categories
3468:sildenafil
3448:nifedipine
3351:Cofactors:
3340:N-Hydroxy-
3247:N-Hydroxy-
3036:Canavanine
3031:BYK-191023
2850:inhibitors
2779:REC15/2739
2758:V-PYRRO/NO
2448:Nicorandil
2337:Vericiguat
2236:modulators
1819:amino acid
1736:Si donors:
1266:. Oxford:
805:21 October
782:References
752:signalling
254:tetrahedra
98:Co(NO)(CO)
3508:See also:
3454:Nebivolol
3413:captopril
3335:-Arginine
3276:norvaline
3271:ornithine
3185:GW-273629
3141:N-Methyl-
3087:N-Methyl-
3078:-lysine (
2950:N-Propyl-
2937:N-Methyl-
2918:ARL-17477
2811:Unsorted:
2361:NO donors
2332:Riociguat
2312:BI-703704
2292:Ataciguat
2233:signaling
2068:S donors:
1909:O donors:
1882:P donors:
1844:porphyrin
1791:imidazole
1768:N donors:
1564:C donors:
1533:B donors:
1509:H donors:
1329:221938378
1019:102349334
825:Chem. Rev
682:+ NO → Cp
609:+ 2OH ⇌ L
597:Reactions
46:complexes
3475:caffeine
3440:blockers
3431:bosentan
3417:losartan
3234:Arginase
3220:VAS-2381
3215:ONO-1714
3163:Unsorted
2923:Indazole
2829:FR146881
2824:FR144220
2814:Cimlanod
2769:Furoxans
2748:PROLI/NO
2718:NONOates
2668:SNO-t-PA
2532:nitrites
2443:NCX-4215
2438:NCX 4040
2433:NCX-4016
2428:NCX-2216
2378:Nitrates
2367:prodrugs
1462:26442594
1426:26197209
1364:15598503
1321:32977718
1011:30957917
924:85546245
916:30920017
845:11942784
572:In some
422:MeCN + 2
389:CoNO(CO)
365:to give
272:symmetry
3493:(e.g.,
3491:Statins
3466:(e.g.,
3442:(e.g.,
3429:(e.g.,
3411:(e.g.,
3261:ginseng
3210:NXN-462
3205:NCX-456
3195:KD-7040
3175:CKD-712
2908:A-84643
2774:Furoxan
2673:SNO-vWF
2423:NCX-466
2272:Targets
1682:& C
1313:1706682
766:giving
738:(DNIC).
495:O + KCN
450:Diazald
357:From NO
262:cluster
3531:Oxides
3322:Others
3281:lysine
2844:Enzyme
2819:FK-409
2733:GLO/NO
2684:SIN-1A
1590:＝CH-CH
1460:
1424:
1362:
1327:
1319:
1311:
1274:
1240:
1207:
1174:
1140:
1107:
1074:
1017:
1009:
922:
914:
876:
843:
590:
586:
489:
473:
424:
420:
395:
387:
385:NO → 2
383:
105:Ni(CO)
58:ligand
3354:NADPH
3149:-NMA)
3136:-NIO)
3095:-NMA)
3082:-NIL)
3069:-NIO)
3011:AEITU
3006:1400W
2958:-NPA)
2945:-NMA)
2932:-NIO)
2618:LA810
2244:Forms
1581:HC(O)
1576:RC(O)
1325:S2CID
1015:S2CID
987:(PDF)
920:S2CID
588:H + 6
535:from
511:2 HNO
430:→ (BF
414:M(CO)
338:trans
172:trans
84:with
3369:Heme
3296:CAMK
3115:eNOS
3105:TRIM
3056:MITU
3051:IPTU
3046:EITU
2983:iNOS
2973:TRIM
2870:nNOS
2738:JS-K
2606:tert
1984:acac
1956:/HCO
1839:bipy
1598:C(CH
1458:PMID
1422:PMID
1360:PMID
1317:PMID
1309:OSTI
1272:ISBN
1238:ISBN
1205:ISBN
1172:ISBN
1138:ISBN
1105:ISBN
1072:ISBN
1007:PMID
961:1974
912:PMID
874:ISBN
841:PMID
807:2022
756:haem
689:2 Cp
678:NbMe
515:→ NO
483:+ NH
426:NOBF
377:(CO)
114:(NO)
103:and
44:are
3382:CaM
3364:FMN
3359:FAD
3309:W-7
3242:ABH
3021:AMT
2861:NOS
2347:ODQ
2281:sGC
2079:NCS
2056:OPR
2032:OSR
2011:ClO
1998:ONO
1976:RCO
1853:Si)
1849:(Me
1834:RCN
1801:RNO
1749:4−n
1747:SiR
1703:≡CR
1695:=CR
1690:RNC
1614:＝CH
1450:doi
1414:doi
1387:doi
1352:doi
1301:doi
1297:142
1230:doi
1197:doi
1164:doi
1130:doi
1097:doi
1042:doi
999:doi
965:doi
904:doi
833:doi
829:102
648:(Ph
635:+ H
619:+ H
615:MNO
543:HNO
523:+ H
487:+ 2
471:+ 2
448:.
418:+ 4
393:+ 2
381:+ 2
313:, .
297:, .
163:).
3527::
3446::
3423:ET
3415:,
3395:Ca
3374:BH
2781:;
2681:):
2675:;
2610:;
2554:):
2548:;
2183:Br
2178:Cl
2146:NC
2137:SR
2117:SO
2087:RS
2048:PO
2040:SO
2027:NO
2003:NO
1993:CO
1952:CO
1934:RO
1897:PR
1889:PR
1873:CS
1829:RN
1814:py
1806:NO
1796:NO
1775:NH
1759:Si
1684:70
1680:60
1653:CO
1648:CO
1643:CN
1622:RC
1610:CH
1586:CH
1540:BR
1456:.
1446:44
1444:.
1420:.
1410:48
1408:.
1383:77
1381:.
1358:.
1348:99
1346:.
1323:.
1315:.
1307:.
1295:.
1236:.
1203:.
1170:.
1136:.
1103:.
1038:11
1036:.
1013:.
1005:.
995:25
993:.
989:.
959:.
947:^
918:.
910:.
900:40
898:.
853:^
839:.
827:.
815:^
797:.
770:.
720:NO
673:Cp
660:P)
652:P)
605::
539::
519:NO
475:NH
397:CO
373:Co
369::
269:3v
183:2g
130:.
74:CO
60:.
3497:)
3484:)
3477:)
3470:)
3460:)
3456:(
3450:)
3433:)
3425:B
3419:)
3407:/
3389:2
3387:O
3376:4
3342:L
3333:L
3249:L
3147:L
3143:L
3134:L
3130:L
3093:L
3089:L
3080:L
3076:L
3067:L
3063:L
2956:L
2952:L
2943:L
2939:L
2930:L
2852:)
2848:(
2786::
2771::
2697::
2593:n
2546:)
2542:2
2534::
2530:/
2467:)
2463:3
2380::
2369:)
2365:(
2222:e
2215:t
2208:v
2188:I
2172:2
2170:F
2165:F
2148:S
2141:O
2139:2
2131:3
2129:O
2127:2
2125:S
2119:2
2111:2
2109:S
2107:2
2105:C
2103:2
2101:R
2096:S
2094:2
2092:R
2081:2
2077:2
2075:R
2058:3
2050:4
2042:4
2034:2
2025:5
2023:H
2021:5
2019:C
2013:4
2005:3
1991:2
1989:R
1978:2
1970:4
1968:O
1966:2
1964:C
1958:3
1954:3
1946:2
1944:O
1939:O
1929:O
1927:2
1925:R
1920:O
1918:2
1916:H
1899:2
1891:3
1871:N
1864:2
1862:N
1857:N
1855:2
1851:3
1824:N
1808:2
1785:3
1783:N
1777:3
1757:3
1755:R
1745:n
1743:H
1726:7
1724:H
1722:9
1720:C
1714:5
1712:H
1710:5
1708:C
1697:2
1678:C
1672:6
1670:R
1668:6
1666:C
1661:C
1655:2
1637:4
1635:H
1633:6
1631:C
1626:R
1624:2
1616:2
1612:2
1604:3
1602:)
1600:2
1592:2
1588:2
1571:R
1554:n
1552:H
1550:m
1548:B
1542:2
1523:2
1521:H
1516:H
1494:e
1487:t
1480:v
1464:.
1452::
1428:.
1416::
1393:.
1389::
1366:.
1354::
1331:.
1303::
1280:.
1246:.
1232::
1213:.
1199::
1180:.
1166::
1146:.
1132::
1113:.
1099::
1080:.
1048:.
1044::
1021:.
1001::
971:.
967::
941:.
926:.
906::
882:.
847:.
835::
809:.
723:x
695:2
691:2
684:2
680:2
676:2
662:2
658:3
654:2
650:3
639:O
637:2
633:2
623:O
621:2
617:2
612:n
592:e
582:2
580:H
545:3
527:O
525:2
521:3
517:2
513:3
493:2
491:H
485:3
481:2
477:2
469:2
467:K
446:n
436:2
434:)
432:4
428:4
416:6
391:3
379:8
375:2
266:C
238:4
116:2
112:2
107:4
100:3
37:.
23:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
(ON)(pyridine)4%2B_(9RUKQOE02).png)