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Criegee intermediate

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Criegee intermediates may be collisionally stabilized via collisions with other molecules in the atmosphere. These stabilized Criegee intermediates may then undergo thermal unimolecular decay to OH radicals and other products, or may undergo bimolecular reactions with other atmospheric species.
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When Criegee intermediates are formed, some portion of them will undergo prompt unimolecular decay, producing OH radicals and other products. However, they may instead become stabilized by interactions with other molecules or react with other chemicals to give different products.
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The alkene ozonolysis reaction is extremely exothermic, releasing about 50 kilocalories per mole (210 kJ/mol) of excess energy. Therefore, the Criegee intermediates are formed with a large amount of internal energy.
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Welz, Oliver; Savee, John D.; Osborn, David L.; Vasu, Subith S.; Percival, Carl J.; Shallcross, Dudley E.; Taatjes, Craig A. (13 January 2012). "Direct Kinetic Measurements of Criegee Intermediate (CH
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Taatjes, Craig A.; Shallcross, Dudley E.; Percival, Carl J.; Vasu, Subith S.; Osborn, David L.; Savee, John D.; Welz, Oliver (2012-01-13). "Direct Kinetic Measurements of Criegee Intermediate (CH
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Criegee intermediates are formed by the gas-phase reactions of alkenes and ozone in the Earth's atmosphere. Ozone adds across the carbon–carbon double bond of the alkene to form a
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Marston, George; Johnson, David (2008-03-25). "The gas-phase ozonolysis of unsaturated volatile organic compounds in the troposphere".
567: 317: 562: 79:). OH radicals are the most important oxidant in the troposphere, and are important in controlling air quality and pollution. 124:, which then decomposes to produce a carbonyl (RR'CO) and a carbonyl oxide. The latter is known as the Criegee intermediate. 75:, which are an important factor in controlling global climate. Criegee intermediates are also an important source of OH ( 144:
In the ozonolysis reaction sequence, the Criegee intermediate reacts with another carbonyl compound (generally the
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Ozone reacts with an alkene to form a carbonyl and a carbonyl oxide, known as a Criegee intermediate.
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Chemistry of the upper and lower atmosphere : theory, experiments, and applications
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The formation of this sort of structure was first postulated in the 1950s by
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byproduct of the Criegee-intermediate formation reaction itself) to form an
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in the Earth's atmosphere, and are implicated in the formation of
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has a substantially zwitterionic character rather than the
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Heard, Dwayne E.; Whalley, Lisa K.; Stone, Daniel (2012).
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with two charge centers. These chemicals may react with
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Finlayson-Pitts, Barbara J.; Pitts, James N. (2000).
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radicals: field measurements and model comparisons"
238:"How mysterious molecules may help cool Earth" 98:character that had previously been proposed. 8: 284: 165: 7: 498: 496: 236:Castro, Joseph (January 12, 2012). 14: 1: 312:. San Diego: Academic Press. 437:Su, Yu-Te; Huang, Yu-Hsuan; 370:OO) Formed by Reaction of CH 177:OO) Formed by Reaction of C 584: 105: 15: 568:Climate change mitigation 505:Chemical Society Reviews 273:Chemical Society Reviews 16:Not to be confused with 563:Environmental chemistry 471:10.1126/science.1234369 400:10.1126/science.1213229 265:"Tropospheric OH and HO 207:10.1126/science.1213229 117: 35: 115: 88:Infrared spectroscopy 30: 22:Criegee rearrangement 156:(1,2,4-trioxolane). 92:electronic structure 40:Criegee intermediate 463:2013Sci...340..174S 392:2012Sci...335..204W 199:2012Sci...335..204W 348:. January 12, 2012 286:10.1039/C2CS35140D 118: 36: 457:(6129): 174–176. 386:(6065): 204–207. 279:(19): 6348–6404. 193:(6065): 204–207. 77:hydroxyl radicals 18:Criegee oxidation 575: 558:Chemical bonding 537: 536: 517:10.1039/B704260B 500: 491: 490: 439:Witek, Henryk A. 434: 428: 427: 363: 357: 356: 354: 353: 338: 332: 331: 305: 299: 298: 288: 260: 254: 253: 251: 250: 233: 227: 226: 170: 583: 582: 578: 577: 576: 574: 573: 572: 543: 542: 541: 540: 502: 501: 494: 448: 436: 435: 431: 377: 373: 369: 365: 364: 360: 351: 349: 340: 339: 335: 320: 307: 306: 302: 268: 262: 261: 257: 248: 246: 235: 234: 230: 184: 180: 176: 172: 171: 167: 162: 134: 110: 104: 69:nitrogen oxides 42:(also called a 25: 12: 11: 5: 581: 579: 571: 570: 565: 560: 555: 545: 544: 539: 538: 511:(4): 699–716. 492: 446: 443:Lee, Yuan-Pern 429: 375: 371: 367: 358: 333: 318: 300: 266: 255: 228: 182: 178: 174: 164: 163: 161: 158: 133: 130: 106:Main article: 103: 100: 84:Rudolf Criegee 65:sulfur dioxide 13: 10: 9: 6: 4: 3: 2: 580: 569: 566: 564: 561: 559: 556: 554: 553:Free radicals 551: 550: 548: 534: 530: 526: 522: 518: 514: 510: 506: 499: 497: 493: 488: 484: 480: 476: 472: 468: 464: 460: 456: 452: 444: 440: 433: 430: 425: 421: 417: 413: 409: 405: 401: 397: 393: 389: 385: 381: 362: 359: 347: 346:Science Daily 343: 337: 334: 329: 325: 321: 319:9780080529073 315: 311: 304: 301: 296: 292: 287: 282: 278: 274: 270: 259: 256: 245: 244: 239: 232: 229: 224: 220: 216: 212: 208: 204: 200: 196: 192: 188: 169: 166: 159: 157: 155: 151: 147: 142: 138: 131: 129: 125: 123: 114: 109: 101: 99: 97: 93: 90:suggests the 89: 85: 80: 78: 74: 70: 66: 62: 59: 55: 54: 48: 47: 41: 34: 29: 23: 19: 508: 504: 454: 450: 432: 383: 379: 361: 350:. Retrieved 336: 309: 303: 276: 272: 258: 247:. Retrieved 241: 231: 190: 186: 168: 143: 139: 135: 126: 119: 81: 50: 43: 39: 37: 547:Categories 352:2012-01-14 249:2012-01-12 160:References 122:molozonide 108:Ozonolysis 46:zwitterion 33:zwitterion 525:1460-4744 408:1095-9203 328:162128929 102:Formation 96:biradical 53:biradical 533:18362978 487:31499893 479:23580523 424:26810853 416:22246773 374:I with O 295:22907645 243:NBC News 223:26810853 215:22246773 181:I with O 146:aldehyde 73:aerosols 58:carbonyl 51:Criegee 44:Criegee 31:Criegee 459:Bibcode 451:Science 388:Bibcode 380:Science 195:Bibcode 187:Science 154:ozonide 132:Removal 56:) is a 531:  523:  485:  477:  422:  414:  406:  326:  316:  293:  221:  213:  150:ketone 483:S2CID 449:OO". 420:S2CID 219:S2CID 61:oxide 529:PMID 521:ISSN 475:PMID 412:PMID 404:ISSN 324:OCLC 314:ISBN 291:PMID 211:PMID 67:and 513:doi 467:doi 455:340 396:doi 384:335 378:". 281:doi 203:doi 191:335 185:". 148:or 49:or 20:or 549:: 527:. 519:. 509:37 507:. 495:^ 481:. 473:. 465:. 453:. 441:; 418:. 410:. 402:. 394:. 382:. 344:. 322:. 289:. 277:41 275:. 271:. 240:. 217:. 209:. 201:. 189:. 38:A 535:. 515:: 489:. 469:: 461:: 447:2 426:. 398:: 390:: 376:2 372:2 368:2 355:. 330:. 297:. 283:: 267:2 252:. 225:. 205:: 197:: 183:2 179:2 175:2 24:.

Index

Criegee oxidation
Criegee rearrangement

zwitterion
zwitterion
biradical
carbonyl
oxide
sulfur dioxide
nitrogen oxides
aerosols
hydroxyl radicals
Rudolf Criegee
Infrared spectroscopy
electronic structure
biradical
Ozonolysis

molozonide
aldehyde
ketone
ozonide
Bibcode
2012Sci...335..204W
doi
10.1126/science.1213229
PMID
22246773
S2CID
26810853

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