489:
31:
2221:
Mandler, Michael D.; Degnan, Andrew P.; Zhang, Shasha; Aulakh, Darpandeep; Georges, Ketleine; Sandhu, Bhupinder; Sarjeant, Amy; Zhu, Yeheng; Traeger, Sarah C.; Cheng, Peter T.; Ellsworth, Bruce A.; Regueiro-Ren, Alicia (28 January 2022). "Structural and
Thermal Characterization of Halogenated
1687:
1003:
control experiments in which it is important to avoid microbial activity. However, it has the disadvantage to be prone to trigger unexpected and undesirable side reactions that can jeopardize the experimental results. Indeed, the azide anion is a
1688:
Committee on
Prudent Practices for Handling, Storage, and Disposal of Chemicals in Laboratories, Board on Chemical Sciences and Technology, Commission on Physical Sciences, Mathematics, and Applications, National Research Council (1995).
1470:
vapors come into contact with heavy metals (Pb, Hg…) or their salts. Heavy-metal azides can accumulate under certain circumstances, for example, in metal pipelines and on the metal components of diverse equipment
1922:
Hendrix, Katrien; Bleyen, Nele; Mennecart, Thierry; Bruggeman, Christophe; Valcke, Elie (2019). "Sodium azide used as microbial inhibitor caused unwanted by-products in anaerobic geochemical studies".
1115:
emission in soil. A proposed explanation is the stimulation of the denitrification processes because of the azide’s role in the synthesis of denitrifying enzymes. Moreover, azide also affects the
1996:
Retelletti Brogi, Simona; Derrien, Morgane; Hur, Jin (2019). "In-depth assessment of the effect of sodium azide on the optical properties of dissolved organic matter".
1278:
4078:
4063:
4108:
4125:
4051:
4028:
3773:
3666:
3383:
828:
to the same corresponding species in each elementary redox reaction considered here above. The respective stability of the reaction products of these three
4090:
4040:
3883:
3642:
4137:
3851:
3704:
3480:
3836:
3824:
3812:
3800:
3654:
3550:
1661:
1295:
3984:
3621:
3434:
3293:
3446:
3371:
1720:
638:) and is favored when the solution is acidified. This is a method of destroying residual azides, prior to disposal. In the process, nitrogen gas (
3609:
3535:
3418:
3395:
4152:
4007:
3996:
2988:
3736:
3012:
3004:
2396:
1428:(HCN). When accidentally present in the air of a laboratory at low concentration, it can cause irritations such as nasal stuffiness, or
1413:
of 27 mg/kg in rats) and can be absorbed through the skin. When sodium azide enters in contact with an acid, it produces volatile
1884:
Goel, Ramesh K; Cooper, Adrienne T; Flora, Joseph R.V (2003-09-01). "Sodium azide interference in chemical and biological testing".
2093:
2074:
2079:
1542:
852:
In 2005, about 251 tons of azide-containing compounds were annually produced in the world, the main product being sodium azide.
1593:
1540:
S. Bräse; C. Gil; K. Knepper; V. Zimmermann (2005). "Organic Azides: An
Exploding Diversity of a Unique Class of Compounds".
1139:
analyses and they should be systematically identified and first rigorously tested in the laboratory before to use azide as
1024:. Therefore, it is susceptible to interfere in an unpredictable way with many substances. For example, the azide anion can
1319:
333:
Azide salts can decompose with release of nitrogen gas. The decomposition temperatures of the alkali metal azides are:
1704:
80:
3107:
2389:
2163:
2324:"Sodium azide: A potential hazard when used to eliminate interferences in the iodometric determination of sulfur"
1754:
421:
1609:
Müller, Thomas G.; Karau, Friedrich; Schnick, Wolfgang; Kraus, Florian (2014). "A New Route to Metal Azides".
2265:
Tat, John; Heskett, Karen; Satomi, Shiho; Pilz, Renate B.; Golomb, Beatrice A.; Boss, Gerry R. (2021-08-03).
1245:, it gives the following series of oxidation reactions when the redox couples are presented as reductants:
1351:) reactions, where copper(I) catalyzes the cycloaddition of an organoazide to a terminal alkyne, forming a
578:
2369:
2382:
1488:
961:
435:
89:
2363:
1372:
1124:
230:
3085:
427:
Many inorganic covalent azides (e.g., chlorine, bromine, and iodine azides) have been described.
1690:
2891:
2436:
2323:
1696:
1158:
is used to purify metallic sodium in laboratories handling molten sodium used as a coolant for
17:
873:. It decomposes on heating to give nitrogen gas, which is used to quickly expand the air bag:
2967:
2870:
2486:
1585:
450:
221:
Many inorganic azides can be prepared directly or indirectly from sodium azide. For example,
3716:
3100:
2902:
2883:
2681:
2669:
1376:
1159:
241:
dissolved in liquid ammonia. Some azides are produced by treating the carbonate salts with
1849:
Lindner, Pinhas; Shomer, Ilan (1984). "Interference of azide in assays of carbohydrates".
1479:
equipment, cooling traps, water baths, waste pipes), and thus lead to violent explosions.
561:
on the right. As seen on the Frost diagram the disproportionation reaction lowers ∆G, the
8:
3562:
2910:
2875:
2626:
1794:"Problems associated with the use of azide as an inhibitor of microbial activity in soil"
581:). By minimizing the energy in the system, the disproportionation reaction increases its
319:
315:
3305:
2918:
2781:
2618:
2299:
2266:
2247:
2196:
1714:
1463:
when heated or shaken. Heavy-metal azides are formed when solutions of sodium azide or
1454:
1407:
1013:
829:
602:
516:
479:
475:
443:
301:
112:
2134:
2117:
2032:
1826:
1793:
3194:
2794:
2343:
2304:
2286:
2251:
2239:
2200:
2188:
2180:
2139:
2098:
2013:
1978:
1939:
1901:
1866:
1862:
1831:
1813:
1750:
1700:
1626:
1589:
1559:
1472:
957:
821:
562:
311:
2033:"Problems in the use of molten sodium as transfer fluid. OSTI declassified document"
1935:
1659:
I. C. Tornieporth-Oetting & T. M. Klapötke (1995). "Covalent
Inorganic Azides".
1219:
impurities still present into the sodium bath. The reaction residue is only gaseous
3511:
3469:
3320:
3205:
3063:
2842:
2737:
2662:
2534:
2335:
2294:
2278:
2231:
2172:
2158:
2129:
2088:
2055:
2005:
1970:
1931:
1893:
1858:
1821:
1805:
1742:
1670:
1618:
1577:
1551:
1425:
1325:
570:
462:
148:
137:
97:
93:
56:
2282:
1809:
4217:
3595:
3504:
3457:
3349:
3281:
3159:
3093:
3025:
2827:
2725:
1329:
1315:
1104:
1017:
817:
2235:
909:
which violently decompose to the corresponding metal and nitrogen, for example:
3871:
3863:
3587:
3407:
3336:
3260:
3228:
3217:
3171:
3132:
2979:
2934:
2926:
2606:
2593:
2571:
2470:
2009:
1457:
1414:
1403:
1368:
1178:
1140:
1021:
996:
782:
778:
594:
582:
524:
391:
258:
242:
193:
123:
119:
1737:
Jobelius, Horst H.; Scharff, Hans-Dieter (2005). "Hydrazoic Acid and Azides".
4211:
3750:
3686:
3574:
3357:
3151:
3043:
2942:
2805:
2789:
2760:
2449:
2347:
2339:
2290:
2184:
2017:
1982:
1943:
1905:
1870:
1817:
1746:
1476:
1344:
1085:
797:
523:
of nitrogen. This diagram shows the significant energetic instability of the
520:
492:
483:
286:
275:
254:
171:
133:
39:
2176:
237:
and sodium azide. An alternative route is direct reaction of the metal with
3909:
3758:
3728:
3678:
3492:
3273:
3183:
3051:
2996:
2950:
2814:
2638:
2614:
2576:
2308:
2243:
2192:
2143:
2102:
1835:
1674:
1630:
1622:
1563:
1555:
1435:
1392:
1388:
1190:
1132:
1120:
1066:
940:
930:
860:
809:
238:
234:
183:
167:
2094:
10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
488:
2958:
2744:
2693:
2657:
2059:
1500:
1495:
1333:
1166:
1039:
1005:
431:
3523:
2566:
1974:
1692:
Prudent practices in the laboratory: handling and disposal of chemicals
1658:
1460:
1439:
1116:
891:
361:(390 °C). This method is used to produce ultrapure alkali metals:
222:
152:
2075:"Click Chemistry: Diverse Chemical Function from a Few Good Reactions"
2050:
Huisgen, R. (1961). "Centenary
Lecture – 1,3-Dipolar Cycloadditions".
1363:
A very damaging and illegal usage of sodium azide is its diversion by
3236:
3039:
2769:
2712:
2552:
2458:
1539:
1337:
906:
226:
46:
1897:
3115:
3047:
2733:
2544:
2428:
2405:
2374:
2072:
1429:
1364:
1352:
990:
574:
552:
534:
533:(or the azide ion) surrounded by two much more stable species, the
2222:
Azidopyridines: Under-Reported
Synthons for Medicinal Chemistry".
2159:"How Dangerous is too Dangerous? A Perspective on Azide Chemistry"
469:
3069:
3057:
3033:
2700:
2645:
2588:
2561:
2539:
2529:
2444:
2420:
1774:(5th ed.). New York: W. H. Freeman and Company. p. 382.
1136:
1070:
1062:
1000:
813:
439:
268:
156:
1957:
Aulakh, M. S.; Rennie, D. A. (1985-02-01). "Azide effects upon N
1921:
1341:
1206:
1028:
870:
417:
1648:. Vol. 1 (2nd ed.). NY: Academic Press. p. 475.
1131:. Many other interferences are reported in the literature for
460:, generating a metal complex in unusual oxidation states (see
2521:
2516:
2508:
1348:
1059:
1025:
1009:
825:
786:
598:
512:
508:
504:
1169:
form of the azide anion, has a very low reduction potential
3075:
1128:
68:
62:
30:
1995:
2118:"The growing impact of click chemistry on drug discovery"
1644:
Dönges, E. (1963). "Alkali Metals". In Brauer, G. (ed.).
1205:, in a special anaerobic glovebox with very low residual
537:
2220:
844:, as can be verified in the Frost diagram for nitrogen.
438:
for both aliphatic and aromatic systems. It reacts with
1608:
496:
2157:
Treitler, Daniel S.; Leung, Simon (2 September 2022).
588:
995:
Sodium azide is commonly used in the laboratory as a
855:
81:
65:
2370:
Synthesizing, purifying, and handling organic azides
2264:
442:, causing a ring-opening; it undergoes Michael-like
71:
2115:
1989:
59:
1662:Angewandte Chemie International Edition in English
2322:Haas, Jonathan M.; Marsh, William W. (May 1970).
1576:
4209:
2073:H. C. Kolb; M. G. Finn; K. B. Sharpless (2001).
1886:Journal of Environmental Engineering and Science
1146:
991:Microbial inhibitor and undesirable side effects
593:Azides decompose with nitrite compounds such as
2328:American Industrial Hygiene Association Journal
1961:O emission and transformations of N in soils".
1883:
1736:
470:Redox behaviour and trend to disproportionation
424:. Some such compound are more shock sensitive.
1917:
1915:
1739:Ullmann's Encyclopedia of Industrial Chemistry
1371:to poison some animal species by blocking the
1201:= -2,71 volt) under strict anoxic conditions (
3101:
2390:
2156:
2052:Proceedings of the Chemical Society of London
1848:
1791:
1787:
1785:
1783:
1781:
151:. The dominant application of azides is as a
2267:"Sodium azide poisoning: A narrative review"
1956:
1719:: CS1 maint: multiple names: authors list (
2049:
1912:
1842:
1646:Handbook of Preparative Inorganic Chemistry
832:redox reactions is in the following order:
577:exchanged in the redox reaction, and E the
3108:
3094:
2397:
2383:
2030:
1950:
1792:Rozycki, Michael; Bartha, Richard (1981).
1778:
999:agent to avoid microbial proliferation in
605:reaction because two different N-species (
2321:
2298:
2133:
2092:
2031:Weber, C. E. (July 1948 – January 1951).
2024:
1825:
1769:
1732:
1730:
2315:
1877:
1535:
1533:
1531:
1193:can be added to molten metallic sodium (
487:
449:Azides can be used as precursors of the
170:is made industrially by the reaction of
29:
2258:
2080:Angewandte Chemie International Edition
1543:Angewandte Chemie International Edition
626:) converge to a same one (respectively
446:to 1,4-unsaturated carbonyl compounds.
390:Protonation of azide salts gives toxic
14:
4210:
3141:
3116:Salts and covalent derivatives of the
1798:Applied and Environmental Microbiology
1727:
1643:
1432:and death at elevated concentrations.
3973:
3089:
2378:
1528:
1177:= -3,09 volt, and is even a stronger
2404:
2116:Kolb, H.C.; Sharpless, B.K. (2003).
318:, azide can be described by several
1107:, ZVI). Azide can also enhance the
589:Destruction by oxidation by nitrite
24:
2037:Journal of Metallurgy and Ceramics
1320:Azide-alkyne Huisgen cycloaddition
1309:
956:Some organic azides are potential
856:Primary explosives and propellants
25:
4229:
2357:
394:in the presence of strong acids:
2164:The Journal of Organic Chemistry
1963:Canadian Journal of Soil Science
869:is the propellant in automobile
515:, as they are easily subject to
422:transition metal azide complexes
55:
2214:
2150:
2109:
2066:
2043:
1936:10.1016/j.apgeochem.2019.05.014
847:
1763:
1681:
1652:
1637:
1602:
1570:
551:on the left and the molecular
162:
27:Anion and chemical group (–N3)
13:
1:
2283:10.1080/15563650.2021.1906888
2135:10.1016/S1359-6446(03)02933-7
1810:10.1128/aem.41.3.833-836.1981
1522:
1358:
1147:Purification of molten sodium
430:The azide anion behaves as a
1863:10.1016/0308-8146(84)90053-0
1424:), as toxic and volatile as
890:Heavy metal azides, such as
579:standard electrode potential
453:by being induced to release
328:
7:
2364:Synthesis of organic azides
2236:10.1021/acs.orglett.1c03201
1482:
1016:, it can behave both as an
229:, may be prepared from the
10:
4234:
3975:
2010:10.1007/s10895-019-02398-w
1489:Homoleptic azido compounds
1313:
1143:for a given application.
1123:optical properties of the
503:Azides have an ambivalent
473:
248:
37:
3143:
3125:
3024:
2863:
2605:
2501:
2413:
1582:Chemistry of the Elements
1580:; Earnshaw, Alan (1997).
1391:and respiratory poisons.
1382:
1189:= -3.04 volt), dry solid
962:2-dimethylaminoethylazide
436:nucleophilic substitution
322:; an important one being
2340:10.1080/0002889708506248
1747:10.1002/14356007.a13_193
1373:electron transport chain
1328:is commonly utilized in
1125:dissolved organic matter
1038:) with the formation of
1012:species. Being prone to
519:, as illustrated by the
507:behavior: they are both
495:for nitrogen species at
38:For organic azides, see
2177:10.1021/acs.joc.2c01402
1998:Journal of Fluorescence
1741:. Weinheim: Wiley-VCH.
1165:As hydrazoic acid, the
645:) and nitrogen oxides (
451:metal nitrido complexes
147:, containing the azide
1697:National Academy Press
1675:10.1002/anie.199505111
1623:10.1002/anie.201404561
1556:10.1002/anie.200400657
905:, are shock-sensitive
500:
35:
1586:Butterworth-Heinemann
1578:Greenwood, Norman N.
1406:(NaCN) (with an oral
1160:fast-neutron reactors
1069:. It can also reduce
491:
33:
2060:10.1039/PS9610000357
1924:Applied Geochemistry
1695:. Washington, D.C.:
1377:cellular respiration
953:are used similarly.
824:) is simultaneously
653:and NO) are formed:
320:resonance structures
2271:Clinical Toxicology
2171:(17): 11293–11295.
1772:Inorganic Chemistry
1617:(50): 13695–13697.
1367:as a substitute of
1141:microbial inhibitor
960:, an example being
601:reaction is also a
354:(395 °C), and
316:valence bond theory
231:metathesis reaction
1975:10.4141/cjss85-021
1473:rotary evaporators
1014:disproportionation
958:rocket propellants
830:comproportionation
603:comproportionation
597:. Each elementary
573:, z the number of
517:disproportionation
501:
480:Comproportionation
476:Disproportionation
444:conjugate addition
302:beryllium fluoride
36:
4205:
4204:
4199:
4198:
3083:
3082:
2128:(24): 1128–1137.
2122:Drug Discov Today
2087:(11): 2004–2021.
1770:Shriver; Atkins.
1611:Angewandte Chemie
1595:978-0-08-037941-8
1550:(33): 5188–5240.
1402:) is as toxic as
1213:(< 1 ppm vol.)
822:electron acceptor
569:, where F is the
563:Gibbs free energy
312:cyanogen fluoride
140:with the formula
138:organic compounds
16:(Redirected from
4225:
3129:
3128:
3110:
3103:
3096:
3087:
3086:
3073:
3061:
3037:
3026:Oxidation states
2855:
2854:
2823:
2822:
2757:
2756:
2721:
2720:
2709:
2708:
2654:
2653:
2399:
2392:
2385:
2376:
2375:
2366:, recent methods
2352:
2351:
2319:
2313:
2312:
2302:
2262:
2256:
2255:
2218:
2212:
2211:
2209:
2207:
2154:
2148:
2147:
2137:
2113:
2107:
2106:
2096:
2070:
2064:
2063:
2047:
2041:
2040:
2028:
2022:
2021:
1993:
1987:
1986:
1954:
1948:
1947:
1919:
1910:
1909:
1881:
1875:
1874:
1846:
1840:
1839:
1829:
1789:
1776:
1775:
1767:
1761:
1760:
1734:
1725:
1724:
1718:
1710:
1685:
1679:
1678:
1656:
1650:
1649:
1641:
1635:
1634:
1606:
1600:
1599:
1584:(2nd ed.).
1574:
1568:
1567:
1537:
1517:
1516:
1515:
1512:
1469:
1452:
1438:azides, such as
1423:
1401:
1326:functional group
1296:
1293:
1279:
1276:
1262:
1259:
1225:
1218:
1214:
1157:
1114:
1102:
1098:
1094:
1083:
1082:
1081:
1078:
1057:
1056:
1055:
1052:
1037:
986:
952:
938:
926:
904:
886:
868:
843:
812:(NO) (+2) while
807:
795:
769:
767:
759:
758:
755:
750:
749:
746:
741:
733:
727:
719:
718:
715:
710:
709:
706:
696:
694:
687:
679:
678:
675:
670:
666:
665:
662:
652:
644:
637:
625:
624:
623:
620:
615:
614:
611:
571:Faraday constant
568:
560:
550:
549:
548:
545:
532:
463:high-valent iron
459:
412:
407:
406:
403:
386:
380:
379:
378:
375:
370:
360:
353:
346:
339:
325:
309:
299:
298:
297:
294:
284:
273:
266:
217:
191:
181:
149:functional group
146:
131:
117:
110:
109:
108:
105:
94:polyatomic anion
84:
78:
77:
74:
73:
70:
67:
64:
61:
21:
4233:
4232:
4228:
4227:
4226:
4224:
4223:
4222:
4208:
4207:
4206:
4201:
4200:
4164:
4160:
4156:
4145:
4141:
4133:
4129:
4116:
4112:
4098:
4094:
4086:
4082:
4071:
4067:
4059:
4055:
4050:
4048:
4044:
4036:
4032:
4015:
4011:
4006:
4004:
4000:
3992:
3988:
3917:
3913:
3891:
3887:
3879:
3875:
3867:
3859:
3855:
3850:
3848:
3844:
3840:
3832:
3828:
3820:
3816:
3808:
3804:
3781:
3777:
3766:
3762:
3754:
3744:
3740:
3732:
3724:
3720:
3712:
3708:
3694:
3690:
3682:
3674:
3670:
3662:
3658:
3650:
3646:
3629:
3625:
3617:
3613:
3603:
3599:
3591:
3578:
3570:
3566:
3558:
3554:
3543:
3539:
3531:
3527:
3519:
3515:
3510:
3508:
3500:
3496:
3488:
3484:
3479:
3477:
3473:
3465:
3461:
3456:
3454:
3450:
3442:
3438:
3430:
3426:
3422:
3417:
3415:
3411:
3403:
3399:
3391:
3387:
3379:
3375:
3365:
3361:
3353:
3340:
3332:
3328:
3324:
3313:
3309:
3301:
3297:
3289:
3285:
3277:
3264:
3253:
3249:
3245:
3244:
3240:
3235:
3232:
3227:
3225:
3221:
3213:
3209:
3204:
3202:
3198:
3193:
3191:
3187:
3179:
3175:
3167:
3163:
3155:
3136:
3121:
3114:
3084:
3079:
3067:
3055:
3031:
3020:
3016:
3008:
3000:
2992:
2983:
2975:
2971:
2962:
2954:
2946:
2938:
2930:
2922:
2914:
2906:
2896:
2887:
2879:
2859:
2853:
2850:
2849:
2848:
2846:
2839:
2835:
2831:
2821:
2818:
2817:
2816:
2809:
2802:
2798:
2785:
2777:
2773:
2764:
2755:
2752:
2751:
2750:
2748:
2741:
2729:
2719:
2716:
2715:
2714:
2707:
2704:
2703:
2702:
2697:
2689:
2685:
2677:
2673:
2666:
2652:
2649:
2648:
2647:
2642:
2634:
2630:
2622:
2601:
2597:
2584:
2580:
2556:
2548:
2525:
2512:
2497:
2491:
2482:
2474:
2466:
2462:
2453:
2440:
2432:
2424:
2409:
2403:
2360:
2355:
2320:
2316:
2263:
2259:
2224:Organic Letters
2219:
2215:
2205:
2203:
2155:
2151:
2114:
2110:
2071:
2067:
2048:
2044:
2029:
2025:
1994:
1990:
1960:
1955:
1951:
1920:
1913:
1898:10.1139/s03-043
1882:
1878:
1847:
1843:
1790:
1779:
1768:
1764:
1757:
1735:
1728:
1712:
1711:
1707:
1686:
1682:
1657:
1653:
1642:
1638:
1607:
1603:
1596:
1588:. p. 433.
1575:
1571:
1538:
1529:
1525:
1513:
1510:
1509:
1504:
1485:
1468:
1464:
1458:high explosives
1451:
1447:
1443:
1426:cyanhydric acid
1422:
1418:
1411:
1400:
1396:
1385:
1361:
1330:click chemistry
1322:
1316:Click chemistry
1314:Main articles:
1312:
1310:Click chemistry
1304:
1294:
1291:
1287:
1277:
1274:
1270:
1260:
1258:(g) + 2 H + 2 e
1257:
1253:
1249:
1244:
1236:
1224:
1220:
1216:
1212:
1210:
1200:
1188:
1176:
1156:
1152:
1149:
1112:
1108:
1105:zerovalent iron
1100:
1096:
1092:
1088:
1079:
1076:
1075:
1073:
1053:
1050:
1049:
1047:
1043:
1036:
1032:
993:
985:
981:
977:
973:
969:
965:
951:
947:
943:
937:
933:
925:
921:
917:
913:
903:
899:
895:
885:
881:
877:
867:
863:
858:
850:
841:
837:
833:
805:
801:
794:
790:
765:
763:
756:
753:
752:
747:
744:
743:
739:
738:
731:
725:
723:
716:
713:
712:
707:
704:
703:
701:
692:
691:
685:
683:
676:
673:
672:
668:
663:
660:
659:
657:
650:
646:
643:
639:
635:
631:
627:
621:
618:
617:
612:
609:
608:
606:
591:
583:thermodynamical
566:
559:
555:
546:
543:
542:
540:
531:
527:
486:
474:Main articles:
472:
458:
454:
434:; it undergoes
420:forms numerous
411:
404:
401:
400:
398:
385:
381:
376:
373:
372:
371:
369:
365:
359:
355:
352:
348:
347:(355 °C),
345:
341:
340:(275 °C),
338:
334:
331:
323:
308:
304:
295:
292:
291:
289:
282:
278:
271:
265:
261:
251:
216:
212:
208:
204:
200:
190:
186:
179:
175:
165:
145:
141:
130:
126:
115:
106:
103:
102:
100:
82:
58:
54:
43:
34:The azide anion
28:
23:
22:
15:
12:
11:
5:
4231:
4221:
4220:
4203:
4202:
4197:
4196:
4193:
4190:
4187:
4184:
4181:
4178:
4175:
4172:
4169:
4166:
4162:
4158:
4154:
4150:
4147:
4143:
4139:
4135:
4131:
4127:
4123:
4119:
4118:
4114:
4110:
4106:
4103:
4100:
4096:
4092:
4088:
4084:
4080:
4076:
4073:
4069:
4065:
4061:
4057:
4053:
4046:
4042:
4038:
4034:
4030:
4026:
4023:
4020:
4017:
4013:
4009:
4002:
3998:
3994:
3990:
3986:
3982:
3978:
3977:
3974:
3971:
3970:
3967:
3964:
3961:
3958:
3955:
3952:
3949:
3946:
3943:
3940:
3937:
3934:
3931:
3928:
3925:
3922:
3919:
3915:
3911:
3907:
3903:
3902:
3899:
3896:
3893:
3889:
3885:
3881:
3877:
3873:
3869:
3865:
3861:
3857:
3853:
3846:
3842:
3838:
3834:
3830:
3826:
3822:
3818:
3814:
3810:
3806:
3802:
3798:
3795:
3792:
3789:
3786:
3783:
3779:
3775:
3771:
3768:
3764:
3760:
3756:
3752:
3747:
3746:
3742:
3738:
3734:
3730:
3726:
3722:
3718:
3714:
3710:
3706:
3702:
3699:
3696:
3692:
3688:
3684:
3680:
3676:
3672:
3668:
3664:
3660:
3656:
3652:
3648:
3644:
3640:
3637:
3634:
3631:
3627:
3623:
3619:
3615:
3611:
3607:
3605:
3601:
3597:
3593:
3589:
3584:
3583:
3580:
3576:
3572:
3568:
3564:
3560:
3556:
3552:
3548:
3545:
3541:
3537:
3533:
3529:
3525:
3521:
3517:
3513:
3506:
3502:
3498:
3494:
3490:
3486:
3482:
3475:
3471:
3467:
3463:
3459:
3452:
3448:
3444:
3440:
3436:
3432:
3428:
3424:
3420:
3413:
3409:
3405:
3401:
3397:
3393:
3389:
3385:
3381:
3377:
3373:
3369:
3367:
3363:
3359:
3355:
3351:
3346:
3345:
3342:
3338:
3334:
3330:
3326:
3322:
3318:
3315:
3311:
3307:
3303:
3299:
3295:
3291:
3287:
3283:
3279:
3275:
3270:
3269:
3266:
3262:
3258:
3255:
3251:
3247:
3242:
3238:
3230:
3223:
3219:
3215:
3211:
3207:
3200:
3196:
3189:
3185:
3181:
3177:
3173:
3169:
3165:
3161:
3157:
3153:
3148:
3147:
3144:
3142:
3140:
3138:
3134:
3127:
3126:
3123:
3122:
3113:
3112:
3105:
3098:
3090:
3081:
3080:
3030:
3028:
3022:
3021:
3019:
3018:
3014:
3010:
3006:
3002:
2998:
2994:
2990:
2986:
2981:
2977:
2973:
2969:
2965:
2960:
2956:
2952:
2948:
2944:
2940:
2936:
2932:
2928:
2924:
2920:
2916:
2912:
2908:
2904:
2900:
2894:
2889:
2885:
2881:
2877:
2873:
2867:
2865:
2861:
2860:
2858:
2857:
2851:
2844:
2837:
2833:
2829:
2825:
2819:
2812:
2807:
2800:
2796:
2792:
2783:
2779:
2775:
2771:
2767:
2762:
2753:
2746:
2739:
2731:
2727:
2723:
2717:
2705:
2695:
2691:
2687:
2683:
2679:
2675:
2671:
2664:
2660:
2650:
2640:
2636:
2632:
2628:
2624:
2620:
2611:
2609:
2603:
2602:
2600:
2599:
2595:
2591:
2586:
2582:
2578:
2574:
2569:
2564:
2559:
2554:
2550:
2546:
2542:
2537:
2532:
2527:
2523:
2519:
2514:
2510:
2505:
2503:
2499:
2498:
2496:
2495:
2489:
2484:
2480:
2476:
2472:
2468:
2464:
2460:
2456:
2451:
2447:
2442:
2438:
2434:
2430:
2426:
2422:
2417:
2415:
2411:
2410:
2402:
2401:
2394:
2387:
2379:
2373:
2372:
2367:
2359:
2358:External links
2356:
2354:
2353:
2334:(3): 318–321.
2314:
2277:(8): 683–697.
2257:
2230:(3): 799–803.
2213:
2149:
2108:
2065:
2042:
2023:
2004:(4): 877–885.
1988:
1969:(1): 205–212.
1958:
1949:
1911:
1892:(5): 407–411.
1876:
1857:(2): 141–153.
1851:Food Chemistry
1841:
1804:(3): 833–836.
1777:
1762:
1755:
1726:
1705:
1680:
1669:(5): 511–520.
1651:
1636:
1601:
1594:
1569:
1526:
1524:
1521:
1520:
1519:
1498:
1492:
1491:
1484:
1481:
1466:
1449:
1445:
1420:
1415:hydrazoic acid
1409:
1404:sodium cyanide
1398:
1384:
1381:
1369:sodium cyanide
1360:
1357:
1311:
1308:
1307:
1306:
1302:
1289:
1285:
1272:
1268:
1255:
1251:
1242:
1234:
1222:
1208:
1198:
1186:
1181:than lithium (
1174:
1154:
1148:
1145:
1110:
1090:
1045:
1034:
1022:reducing agent
997:bacteriostatic
992:
989:
983:
979:
975:
971:
967:
949:
945:
935:
928:
927:
923:
919:
915:
901:
897:
888:
887:
883:
879:
865:
857:
854:
849:
846:
839:
835:
803:
792:
783:electron donor
776:
771:
770:
761:
735:
734:
729:
721:
698:
697:
689:
681:
648:
641:
633:
629:
595:sodium nitrite
590:
587:
565:of the system
557:
529:
525:hydrazoic acid
471:
468:
456:
414:
413:
409:
392:hydrazoic acid
388:
387:
383:
367:
357:
350:
343:
336:
330:
327:
306:
280:
263:
259:carbon dioxide
250:
247:
243:hydrazoic acid
219:
218:
214:
210:
206:
202:
194:liquid ammonia
188:
177:
164:
161:
143:
134:Organic azides
128:
124:hydrazoic acid
120:conjugate base
26:
9:
6:
4:
3:
2:
4230:
4219:
4216:
4215:
4213:
4194:
4191:
4188:
4185:
4182:
4179:
4176:
4173:
4170:
4167:
4165:
4151:
4148:
4146:
4136:
4134:
4124:
4121:
4120:
4117:
4107:
4104:
4101:
4099:
4089:
4087:
4077:
4074:
4072:
4062:
4060:
4049:
4039:
4037:
4027:
4024:
4021:
4018:
4016:
4005:
3995:
3993:
3983:
3980:
3979:
3972:
3968:
3965:
3962:
3959:
3956:
3953:
3950:
3947:
3944:
3941:
3938:
3935:
3932:
3929:
3926:
3923:
3920:
3918:
3908:
3905:
3904:
3900:
3897:
3894:
3892:
3882:
3880:
3870:
3868:
3862:
3860:
3849:
3835:
3833:
3823:
3821:
3811:
3809:
3799:
3796:
3793:
3790:
3787:
3784:
3782:
3772:
3769:
3767:
3757:
3755:
3749:
3748:
3745:
3735:
3733:
3727:
3725:
3715:
3713:
3703:
3700:
3697:
3695:
3685:
3683:
3677:
3675:
3665:
3663:
3653:
3651:
3641:
3638:
3635:
3632:
3630:
3620:
3618:
3608:
3606:
3604:
3594:
3592:
3586:
3585:
3581:
3579:
3573:
3571:
3561:
3559:
3549:
3546:
3544:
3534:
3532:
3522:
3520:
3509:
3503:
3501:
3491:
3489:
3478:
3468:
3466:
3455:
3445:
3443:
3433:
3431:
3416:
3406:
3404:
3394:
3392:
3382:
3380:
3370:
3368:
3366:
3356:
3354:
3348:
3347:
3343:
3341:
3335:
3333:
3319:
3316:
3314:
3304:
3302:
3292:
3290:
3280:
3278:
3272:
3271:
3267:
3265:
3259:
3256:
3254:
3234:
3226:
3216:
3214:
3203:
3192:
3182:
3180:
3170:
3168:
3158:
3156:
3150:
3149:
3145:
3139:
3137:
3131:
3130:
3124:
3119:
3111:
3106:
3104:
3099:
3097:
3092:
3091:
3088:
3077:
3072:
3071:
3065:
3060:
3059:
3053:
3049:
3045:
3041:
3036:
3035:
3029:
3027:
3023:
3017:
3011:
3009:
3003:
3001:
2995:
2993:
2987:
2985:
2978:
2976:
2966:
2964:
2957:
2955:
2949:
2947:
2941:
2939:
2933:
2931:
2925:
2923:
2917:
2915:
2909:
2907:
2901:
2898:
2897:
2890:
2888:
2882:
2880:
2874:
2872:
2869:
2868:
2866:
2862:
2856:
2840:
2826:
2824:
2813:
2811:
2803:
2793:
2791:
2787:
2780:
2778:
2768:
2766:
2758:
2742:
2735:
2732:
2730:
2724:
2722:
2710:
2698:
2692:
2690:
2680:
2678:
2667:
2661:
2659:
2655:
2643:
2637:
2635:
2625:
2623:
2616:
2613:
2612:
2610:
2608:
2604:
2598:
2592:
2590:
2587:
2585:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2551:
2549:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2520:
2518:
2515:
2513:
2507:
2506:
2504:
2500:
2493:
2492:
2485:
2483:
2477:
2475:
2469:
2467:
2457:
2455:
2448:
2446:
2443:
2441:
2435:
2433:
2427:
2425:
2419:
2418:
2416:
2412:
2407:
2400:
2395:
2393:
2388:
2386:
2381:
2380:
2377:
2371:
2368:
2365:
2362:
2361:
2349:
2345:
2341:
2337:
2333:
2329:
2325:
2318:
2310:
2306:
2301:
2296:
2292:
2288:
2284:
2280:
2276:
2272:
2268:
2261:
2253:
2249:
2245:
2241:
2237:
2233:
2229:
2225:
2217:
2202:
2198:
2194:
2190:
2186:
2182:
2178:
2174:
2170:
2166:
2165:
2160:
2153:
2145:
2141:
2136:
2131:
2127:
2123:
2119:
2112:
2104:
2100:
2095:
2090:
2086:
2082:
2081:
2076:
2069:
2061:
2057:
2053:
2046:
2038:
2034:
2027:
2019:
2015:
2011:
2007:
2003:
1999:
1992:
1984:
1980:
1976:
1972:
1968:
1964:
1953:
1945:
1941:
1937:
1933:
1929:
1925:
1918:
1916:
1907:
1903:
1899:
1895:
1891:
1887:
1880:
1872:
1868:
1864:
1860:
1856:
1852:
1845:
1837:
1833:
1828:
1823:
1819:
1815:
1811:
1807:
1803:
1799:
1795:
1788:
1786:
1784:
1782:
1773:
1766:
1758:
1752:
1748:
1744:
1740:
1733:
1731:
1722:
1716:
1708:
1706:0-309-05229-7
1702:
1698:
1694:
1693:
1684:
1676:
1672:
1668:
1664:
1663:
1655:
1647:
1640:
1632:
1628:
1624:
1620:
1616:
1612:
1605:
1597:
1591:
1587:
1583:
1579:
1573:
1565:
1561:
1557:
1553:
1549:
1545:
1544:
1536:
1534:
1532:
1527:
1507:
1502:
1499:
1497:
1494:
1493:
1490:
1487:
1486:
1480:
1478:
1474:
1462:
1459:
1456:
1441:
1437:
1433:
1431:
1427:
1416:
1412:
1405:
1394:
1390:
1389:explosophores
1380:
1378:
1374:
1370:
1366:
1356:
1354:
1350:
1346:
1345:cycloaddition
1343:
1339:
1335:
1331:
1327:
1321:
1317:
1305:= +2,71 volt)
1300:
1292:Na ⇌ Na + e
1290:
1288:= +3,04 volt)
1283:
1275:Li ⇌ Li + e
1273:
1271:= +3,09 volt)
1266:
1248:
1247:
1246:
1240:
1232:
1227:
1211:
1204:
1196:
1192:
1184:
1180:
1172:
1168:
1163:
1161:
1151:Sodium azide
1144:
1142:
1138:
1134:
1130:
1126:
1122:
1118:
1106:
1087:
1086:nitrous oxide
1072:
1068:
1064:
1061:
1041:
1030:
1027:
1023:
1019:
1015:
1011:
1007:
1002:
998:
988:
963:
959:
954:
942:
932:
912:
911:
910:
908:
893:
882:→ 2 Na + 3 N
876:
875:
874:
872:
862:
853:
845:
831:
827:
823:
819:
815:
811:
799:
798:nitrous oxide
788:
784:
780:
774:
737:
736:
700:
699:
656:
655:
654:
604:
600:
596:
586:
584:
580:
576:
572:
564:
554:
539:
536:
526:
522:
521:Frost diagram
518:
514:
510:
506:
498:
494:
493:Frost diagram
490:
485:
484:Frost diagram
481:
477:
467:
465:
464:
452:
447:
445:
441:
437:
433:
428:
425:
423:
419:
397:
396:
395:
393:
364:
363:
362:
326:
321:
317:
313:
303:
288:
287:nitronium ion
277:
276:nitrous oxide
270:
260:
256:
255:isoelectronic
246:
244:
240:
236:
232:
228:
224:
199:
198:
197:
195:
185:
173:
172:nitrous oxide
169:
160:
158:
154:
150:
139:
135:
125:
121:
114:
99:
95:
91:
87:
86:
76:
52:
48:
41:
40:organic azide
32:
19:
3117:
3074:(a strongly
3068:
3056:
3032:
2892:
2487:
2478:
2331:
2327:
2317:
2274:
2270:
2260:
2227:
2223:
2216:
2206:18 September
2204:. Retrieved
2168:
2162:
2152:
2125:
2121:
2111:
2084:
2078:
2068:
2051:
2045:
2036:
2026:
2001:
1997:
1991:
1966:
1962:
1952:
1927:
1923:
1889:
1885:
1879:
1854:
1850:
1844:
1801:
1797:
1771:
1765:
1738:
1691:
1683:
1666:
1660:
1654:
1645:
1639:
1614:
1610:
1604:
1581:
1572:
1547:
1541:
1505:
1477:freezedrying
1434:
1393:Sodium azide
1386:
1362:
1323:
1298:
1281:
1264:
1238:
1230:
1228:
1202:
1194:
1191:sodium azide
1182:
1170:
1164:
1150:
1121:fluorescence
1067:hydroquinone
1010:redox-active
994:
955:
941:barium azide
931:Silver azide
929:
889:
861:Sodium azide
859:
851:
848:Applications
810:nitric oxide
772:
764:O → 10 NO
740:
693:
669:
592:
502:
461:
448:
429:
426:
415:
389:
332:
300:, molecular
252:
239:silver azide
235:lead nitrate
220:
196:as solvent:
184:sodium amide
168:Sodium azide
166:
118:. It is the
50:
44:
2039:(1–6): 291.
1930:: 120–130.
1501:Pentazolate
1496:Pentazenium
1436:Heavy metal
1430:suffocation
1387:Azides are
1133:biochemical
1127:(DOM) from
1040:thiosulfate
1006:nucleophile
922:→ Pb + 3 N
808:) (+1), or
585:stability.
567:(-∆G/F = zE
432:nucleophile
416:Azide as a
213:+ NaOH + NH
163:Preparation
1756:3527306730
1523:References
1440:lead azide
1359:Other uses
1324:The azide
1215:to reduce
1167:protonated
1137:biological
1117:absorbance
907:detonators
892:lead azide
816:(+3) (the
227:detonators
225:, used in
223:lead azide
205:O + 2 NaNH
153:propellant
2348:0002-8894
2291:1556-3650
2252:240154010
2201:252009657
2185:0022-3263
2018:1053-0509
1983:0008-4271
1944:0883-2927
1906:1496-2551
1871:0308-8146
1818:0099-2240
1715:cite book
1461:detonable
1379:process.
1338:catalyzed
1334:copper(I)
1179:reductant
1020:and as a
1018:oxidizing
842:O > NO
779:reductant
575:electrons
509:oxidizing
382:2 M + 3 N
329:Reactions
314:FCN. Per
253:Azide is
113:structure
96:with the
47:chemistry
4212:Category
2841: /
2804: /
2788: /
2759: /
2743: /
2736: /
2711: /
2699: /
2668: /
2656: /
2644: /
2617: /
2517:>C=NR
2414:Hydrides
2406:Nitrogen
2309:34128439
2244:34714083
2193:36052475
2144:14678739
2103:11433435
1836:16345743
1631:24924913
1564:16100733
1483:See also
1365:poachers
1353:triazole
1332:through
787:oxidized
732:O + 6 OH
636:O and NO
553:nitrogen
535:ammonium
513:reducing
440:epoxides
233:between
157:air bags
3976:
2864:Halides
2502:Organic
2408:species
2300:8349855
2054:: 357.
1455:primary
1375:in the
1071:nitrite
1063:quinone
1026:oxidize
1001:abiotic
964:(DMAZ)
871:airbags
826:reduced
818:oxidant
814:nitrite
777:) (the
773:Azide (
269:cyanate
249:Bonding
98:formula
88:) is a
4218:Azides
3078:oxide)
3076:acidic
2607:Oxides
2346:
2307:
2297:
2289:
2250:
2242:
2199:
2191:
2183:
2142:
2101:
2016:
1981:
1942:
1904:
1869:
1834:
1827:243784
1824:
1816:
1753:
1703:
1629:
1592:
1562:
1453:) are
1383:Safety
1342:alkyne
1340:azide-
1261:
1254:⇌ 3 N
1095:, and
1060:reduce
1058:), or
1029:pyrite
1008:and a
838:> N
768:+ 8 OH
766:
751:+ 7 NO
726:
724:O →
711:+ 4 NO
695:+ 4 OH
686:
684:O →
616:and NO
482:, and
418:ligand
90:linear
18:Azides
3118:azide
3046:, 0,
2738:(HON)
2522:-CONR
2248:S2CID
2197:S2CID
1506:cyclo
1349:CuAAC
1129:soils
1099:into
1084:into
1065:into
878:2 NaN
796:(0),
785:) is
760:+ 4 H
720:+ 3 H
680:+ 2 H
599:redox
505:redox
408:→ HN
399:H + N
324:N=N=N
257:with
209:→ NaN
182:with
116:N=N=N
51:azide
4138:Th(N
4126:Ac(N
4109:Yb(N
4091:Ho(N
4079:Dy(N
4064:Gd(N
4052:Eu(N
4041:Eu(N
4029:Sm(N
4008:Ce(N
3997:Ce(N
3985:La(N
3910:Ra(N
3884:Bi(N
3872:Pb(N
3852:Hg(N
3825:Au(N
3813:Pt(N
3801:Ir(N
3774:Lu(N
3759:Ba(N
3737:Xe(N
3717:Te(N
3705:Sb(N
3687:Cd(N
3667:Pd(N
3655:Rh(N
3643:Ru(N
3622:Zr(N
3596:Sr(N
3563:Se(N
3551:As(N
3536:Ga(N
3524:Zn(N
3512:Cu(N
3493:Ni(N
3481:Co(N
3470:Co(N
3458:Fe(N
3447:Fe(N
3435:Mn(N
3408:Cr(N
3396:VO(N
3384:Ti(N
3372:Sc(N
3358:Ca(N
3306:Si(N
3294:Al(N
3282:Mg(N
3206:CO(N
3160:Be(N
3005:NHBr
2997:NHCl
2790:ONOO
2619:(NO)
2572:HNCS
2567:HNCO
2562:HOCN
2545:(CN)
2344:ISSN
2305:PMID
2287:ISSN
2240:PMID
2208:2022
2189:PMID
2181:ISSN
2140:PMID
2099:PMID
2014:ISSN
1979:ISSN
1940:ISSN
1902:ISSN
1867:ISSN
1832:PMID
1814:ISSN
1751:ISBN
1721:link
1701:ISBN
1627:PMID
1590:ISBN
1560:PMID
1444:Pb(N
1318:and
1250:2 HN
1203:e.g.
1135:and
1119:and
944:Ba(N
939:and
914:Pb(N
896:Pb(N
511:and
374:heat
366:2 MN
310:and
187:NaNH
136:are
111:and
85:-zyd
4195:No
4192:Md
4189:Fm
4186:Es
4183:Cf
4180:Bk
4177:Cm
4174:Am
4171:Pu
4168:Np
4149:Pa
4122:**
4105:Tm
4102:Er
4075:Tb
4025:Pm
4022:Nd
4019:Pr
3969:Og
3966:Ts
3963:Lv
3960:Mc
3957:Fl
3954:Nh
3951:Cn
3948:Rg
3945:Ds
3942:Mt
3939:Hs
3936:Bh
3933:Sg
3930:Db
3927:Rf
3924:Lr
3921:**
3906:Fr
3901:Rn
3898:At
3895:Po
3864:TlN
3797:Os
3794:Re
3788:Ta
3785:Hf
3751:CsN
3701:Sn
3698:In
3679:AgN
3639:Tc
3636:Mo
3633:Nb
3610:Y(N
3588:RbN
3582:Kr
3575:BrN
3547:Ge
3505:CuN
3419:CrO
3344:Ar
3337:ClN
3274:NaN
3268:Ne
3250:N–N
3237:N(N
3195:C(N
3172:B(N
3152:LiN
3146:He
3120:ion
3066:,
3013:NHI
2989:NHF
2943:BrN
2935:ClN
2911:NBr
2903:NCl
2899:(?)
2810:NOO
2774:NNO
2734:HNO
2694:HNO
2670:(NO
2639:HNO
2594:-NO
2589:-NO
2557:NCN
2535:HCN
2530:-CN
2494:(?)
2336:doi
2295:PMC
2279:doi
2232:doi
2173:doi
2130:doi
2089:doi
2056:doi
2006:doi
1971:doi
1932:doi
1928:107
1894:doi
1859:doi
1822:PMC
1806:doi
1743:doi
1671:doi
1619:doi
1552:doi
1397:NaN
1243:red
1237:= -
1229:As
1199:red
1187:red
1175:red
1153:NaN
1033:FeS
974:NCH
966:(CH
934:AgN
864:NaN
789:in
728:5 N
702:2 N
688:5 N
658:3 N
632:, N
538:ion
499:= 0
466:).
356:CsN
349:RbN
335:NaN
305:BeF
272:OCN
192:in
155:in
122:of
45:In
4214::
4157:(N
4153:UO
3981:*
3841:(N
3837:Hg
3791:W
3770:*
3729:IN
3423:(N
3350:KN
3325:(N
3321:SO
3317:P
3261:FN
3257:O
3233:NO
3218:NH
3184:CH
3133:HN
3070:+5
3064:+4
3062:,
3058:+3
3054:,
3052:+2
3050:,
3048:+1
3044:−1
3042:,
3040:−2
3038:,
3034:−3
2984:Cl
2980:NH
2959:NH
2951:IN
2927:FN
2919:NI
2893:NF
2884:NF
2876:NF
2871:NF
2815:NO
2799:NO
2795:HO
2786:NO
2782:HO
2726:NO
2713:NO
2701:NO
2663:NO
2658:NO
2646:NO
2615:NO
2577:CH
2540:CN
2509:NR
2488:NH
2471:HN
2454:OH
2450:NH
2437:NH
2429:NH
2421:NH
2342:.
2332:31
2330:.
2326:.
2303:.
2293:.
2285:.
2275:59
2273:.
2269:.
2246:.
2238:.
2228:24
2226:.
2195:.
2187:.
2179:.
2169:87
2167:.
2161:.
2138:.
2124:.
2120:.
2097:.
2085:40
2083:.
2077:.
2035:.
2012:.
2002:29
2000:.
1977:.
1967:65
1965:.
1938:.
1926:.
1914:^
1900:.
1888:.
1865:.
1855:14
1853:.
1830:.
1820:.
1812:.
1802:41
1800:.
1796:.
1780:^
1749:.
1729:^
1717:}}
1713:{{
1699:.
1667:34
1665:.
1625:.
1615:53
1613:.
1558:.
1548:44
1546:.
1530:^
1508:-N
1475:,
1465:HN
1419:HN
1410:50
1408:LD
1355:.
1303:ox
1286:ox
1269:ox
1235:ox
1226:.
1217:Na
1162:.
1101:Fe
1097:Fe
1074:NO
1051:2−
987:.
978:CH
894:,
820:,
781:,
775:-⅓
671:NO
667:+
541:NH
528:HN
497:pH
478:,
342:KN
290:NO
285:,
274:,
267:,
262:CO
245:.
174:,
159:.
142:RN
132:.
127:HN
92:,
83:AY
79:,
69:aɪ
63:eɪ
49:,
4163:2
4161:)
4159:3
4155:2
4144:4
4142:)
4140:3
4132:3
4130:)
4128:3
4115:3
4113:)
4111:3
4097:3
4095:)
4093:3
4085:3
4083:)
4081:3
4070:3
4068:)
4066:3
4058:3
4056:)
4054:3
4047:2
4045:)
4043:3
4035:3
4033:)
4031:3
4014:4
4012:)
4010:3
4003:3
4001:)
3999:3
3991:3
3989:)
3987:3
3916:2
3914:)
3912:3
3890:3
3888:)
3886:3
3878:2
3876:)
3874:3
3866:3
3858:2
3856:)
3854:3
3847:2
3845:)
3843:3
3839:2
3831:4
3829:)
3827:3
3819:6
3817:)
3815:3
3807:6
3805:)
3803:3
3780:3
3778:)
3776:3
3765:2
3763:)
3761:3
3753:3
3743:2
3741:)
3739:3
3731:3
3723:4
3721:)
3719:3
3711:5
3709:)
3707:3
3693:2
3691:)
3689:3
3681:3
3673:2
3671:)
3669:3
3661:6
3659:)
3657:3
3649:6
3647:)
3645:3
3628:4
3626:)
3624:3
3616:3
3614:)
3612:3
3602:2
3600:)
3598:3
3590:3
3577:3
3569:4
3567:)
3565:3
3557:5
3555:)
3553:3
3542:3
3540:)
3538:3
3530:2
3528:)
3526:3
3518:2
3516:)
3514:3
3507:3
3499:2
3497:)
3495:3
3487:3
3485:)
3483:3
3476:2
3474:)
3472:3
3464:3
3462:)
3460:3
3453:2
3451:)
3449:3
3441:2
3439:)
3437:3
3429:2
3427:)
3425:3
3421:2
3414:3
3412:)
3410:3
3402:3
3400:)
3398:3
3390:4
3388:)
3386:3
3378:3
3376:)
3374:3
3364:2
3362:)
3360:3
3352:3
3339:3
3331:2
3329:)
3327:3
3323:2
3312:4
3310:)
3308:3
3300:3
3298:)
3296:3
3288:2
3286:)
3284:3
3276:3
3263:3
3252:3
3248:2
3246:H
3243:3
3241:)
3239:3
3231:3
3229:N
3224:3
3222:N
3220:4
3212:2
3210:)
3208:3
3201:4
3199:)
3197:3
3190:3
3188:N
3186:3
3178:3
3176:)
3174:3
3166:2
3164:)
3162:3
3154:3
3135:3
3109:e
3102:t
3095:v
3015:2
3007:2
2999:2
2991:2
2982:2
2974:2
2972:F
2970:2
2968:N
2963:F
2961:2
2953:3
2945:3
2937:3
2929:3
2921:3
2913:3
2905:3
2895:5
2886:3
2878:2
2852:3
2847:O
2845:2
2843:N
2838:4
2836:O
2834:2
2832:N
2830:4
2828:H
2820:4
2808:2
2806:O
2801:2
2797:2
2784:2
2776:2
2772:2
2770:H
2765:O
2763:2
2761:N
2754:2
2749:O
2747:2
2745:N
2740:2
2728:3
2718:2
2706:3
2696:3
2688:5
2686:O
2684:2
2682:N
2676:2
2674:)
2672:2
2665:2
2651:2
2641:2
2633:3
2631:O
2629:2
2627:N
2621:2
2596:2
2583:2
2581:N
2579:2
2555:2
2553:H
2547:2
2524:2
2511:3
2490:5
2481:3
2479:N
2473:3
2465:4
2463:H
2461:2
2459:N
2452:2
2445:N
2439:2
2431:4
2423:3
2398:e
2391:t
2384:v
2350:.
2338::
2311:.
2281::
2254:.
2234::
2210:.
2175::
2146:.
2132::
2126:8
2105:.
2091::
2062:.
2058::
2020:.
2008::
1985:.
1973::
1959:2
1946:.
1934::
1908:.
1896::
1890:2
1873:.
1861::
1838:.
1808::
1759:.
1745::
1723:)
1709:.
1677:.
1673::
1633:.
1621::
1598:.
1566:.
1554::
1518:)
1514:5
1511:−
1503:(
1471:(
1467:3
1450:2
1448:)
1446:3
1442:(
1421:3
1417:(
1399:3
1395:(
1347:(
1336:-
1301:°
1299:E
1297:(
1284:°
1282:E
1280:(
1267:°
1265:E
1263:(
1256:2
1252:3
1241:°
1239:E
1233:°
1231:E
1223:2
1221:N
1209:2
1207:O
1197:°
1195:E
1185:°
1183:E
1173:°
1171:E
1155:3
1113:O
1111:2
1109:N
1103:(
1093:O
1091:2
1089:N
1080:2
1077:−
1054:3
1048:O
1046:2
1044:S
1042:(
1035:2
1031:(
984:3
982:N
980:2
976:2
972:2
970:)
968:3
950:2
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946:3
936:3
924:2
920:2
918:)
916:3
902:2
900:)
898:3
884:2
880:3
866:3
840:2
836:2
834:N
806:O
804:2
802:N
800:(
793:2
791:N
762:2
757:2
754:−
748:3
745:−
742:N
730:2
722:2
717:2
714:−
708:3
705:−
690:2
682:2
677:2
674:−
664:3
661:−
651:O
649:2
647:N
642:2
640:N
634:2
630:2
628:N
622:2
619:−
613:3
610:−
607:N
558:2
556:N
547:4
544:+
530:3
457:2
455:N
410:3
405:3
402:−
384:2
377:→
368:3
358:3
351:3
344:3
337:3
307:2
296:2
293:+
283:O
281:2
279:N
264:2
215:3
211:3
207:2
203:2
201:N
189:2
180:O
178:2
176:N
144:3
129:3
107:3
104:−
101:N
75:/
72:d
66:z
60:ˈ
57:/
53:(
42:.
20:)
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