306:
4-page addendum to a 26-page article on isomeric butyric acids, and based on very slight experimental evidence even by the standards of the time. Hughes concludes that the rule was an inspired guess, unjustified by the evidence of the time, but which turned out later to be correct (in most cases). A more recent assessment, based on a reading of
Markovnikov's Magistr Khimii and Doktor Khimii dissertations, contradicts this view, and points out that Markovnikov's Rule arises logically from his dissertations.
38:
199:(now Dzerzhinsk, Nizhny Novgorod Oblast, Russian Federation). Soon after his birth, his father retired and settled in a family estate received as a dowry from his wife's family at marriage, in the village of Ivanovo, Knyagininsky district of the Nizhny Novgorod province, where Markovnikov spent his early childhood.
305:
Hughes has discussed the reasons for
Markovnikov's lack of recognition during his lifetime. Although he published mostly in Russian which was not understood by most Western European chemists, the 1870 article in which he first stated his rule was written in German. However the rule was included in a
210:. In 1860, after completing a university course, he was left to prepare for a professorship and was appointed laboratory assistant at a chemical laboratory. In 1864 he defended his master's thesis. In the spring of 1869, he defended his doctoral dissertation.
262:. According to this rule, the nucleophilic X- binds to the carbon (C) atom with fewer hydrogen atoms, while the proton binds to the carbon atom with more hydrogen atoms bonded to it. Thus, hydrogen chloride (HCl) reacts with propene, CH
451:
157:
580:
629:
619:
386:
294:
exhibited both
Markovnikov as well as reversed-order, or anti-Markovnikov, addition, however, was not understood until
61:
624:
406:"Catalytic Markovnikov and anti-Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends"
370:
239:
120:
477:"Ueber die Abhängigkeit der verschiedenen Vertretbarkeit des Radicalwasserstoffs in den isomeren Buttersäuren"
317:
rings with more than six carbon atoms, a ring with four carbon atoms in 1879, and a ring with seven in 1889.
169:
65:
290:
Cl. The rule is useful in predicting the molecular structures of products of addition reactions. Why
584:
203:
206:
in 1856. He moved to the natural department of the university, where he attended the lectures of
541:
Lewis, David E. (2021). "The Logic Behind
Markovnikov's Rule: Was It an Inspired Guess? …No!".
218:
Markovnikov married Lyubov
Dmitrievna Rychkova. They had two sons, Vladimir, a politician and
405:
251:
180:
614:
609:
515:
320:
Markovnikov also showed that butyric and isobutyric acids have the same chemical formula (C
235:
231:
8:
219:
116:
99:
519:
558:
295:
207:
136:
562:
433:
425:
366:
310:
124:
254:, elucidated in 1869 to describe addition reactions of H-X (where 'X' represents a
550:
523:
488:
417:
362:
358:
291:
161:
131:
87:
404:
Beller, Matthias; Seayad, Jayasree; Tillack, Annegret; Jiao, Haijun (2004-06-28).
230:
After a conflict with that university, Markovnikov was appointed professor at the
192:
196:
69:
603:
583:. Institute of Chemistry, Skopje, Macedonia. 18 February 1997. Archived from
492:
429:
238:, where he stayed the rest of his career. He was elected as a member to the
554:
437:
421:
191:
Vladimir
Markovnikov was born on December 22, 1837, in Chernorechye near
527:
37:
183:, that describes addition reactions of hydrogen halides and alkenes.
476:
506:
Hughes, Peter (2006). "Was
Markovnikov's Rule an Inspired Guess?".
349:
Zerong, Wang (2010). "Markovnikov Rule and Anti-Markovnikov Rule".
299:
173:
255:
176:
314:
259:
403:
202:
He joined the cameral department of the law faculty of
298:
offered an explanation in 1933. It is also called The
172:
13 December] 1837 – 11 February 1904) was a
332:) but different structures; i.e., they are isomers.
351:Comprehensive Organic Name Reactions and Reagents
601:
474:
540:
505:
42:Late 19th-century photograph of Markovnikov.
278:rather than the isomeric 1-chloropropane CH
186:
36:
379:
543:Angewandte Chemie International Edition
410:Angewandte Chemie International Edition
602:
348:
234:in 1871 and, two years later, at the
179:, best known for having developed the
387:"Markovnikov, Vladimir Vasiliyevich"
13:
166:Влади́мир Васи́льевич Марко́вников
14:
641:
630:Inventors from the Russian Empire
581:"Vladimir Vasilevich MARKOVNIKOV"
573:
508:The Journal of Chemical Education
397:
620:Chemists from the Russian Empire
309:Markovnikov also contributed to
213:
149:Vladimir Vasilyevich Markovnikov
23:Vladimir Vasilyevich Markovnikov
30:Владимир Васильевич Марковников
534:
499:
468:
444:
363:10.1002/9780470638859.conrr411
342:
250:Markovnikov is best known for
240:American Philosophical Society
121:University of Saint Petersburg
1:
335:
270:to produce 2-chloropropane CH
7:
66:Nizhny Novgorod Governorate
16:Russian chemist (1837–1904)
10:
646:
475:Markownikoff, W. (1870).
225:
204:Kazan Imperial University
165:
142:
130:
112:
105:
95:
76:
47:
35:
28:
21:
625:Russian organic chemists
493:10.1002/jlac.18701530204
187:Early life and education
168:; 25 December [
29:
245:
555:10.1002/anie.202008228
422:10.1002/anie.200300616
391:Encyclopedia Krugosvet
481:Annalen der Pharmacie
456:search.amphilsoc.org
452:"APS Member History"
236:University of Moscow
232:University of Odessa
125:University of Odessa
520:2006JChEd..83.1152H
117:University of Kazan
100:University of Kazan
528:10.1021/ed083p1152
302:effect sometimes.
296:Morris S. Kharasch
252:Markovnikov's rule
181:Markovnikov's rule
137:Alexander Butlerov
416:(26): 3368–3398.
311:organic chemistry
146:
145:
107:Scientific career
80:February 11, 1904
58:December 25, 1837
637:
596:
594:
592:
587:on 16 April 2021
567:
566:
549:(9): 4412–4421.
538:
532:
531:
514:(8): 1152–1154.
503:
497:
496:
472:
466:
465:
463:
462:
448:
442:
441:
401:
395:
394:
383:
377:
376:
346:
292:hydrogen bromide
222:, an architect.
167:
160:
132:Doctoral advisor
90:, Russian Empire
88:Saint Petersburg
83:
57:
55:
40:
19:
18:
645:
644:
640:
639:
638:
636:
635:
634:
600:
599:
590:
588:
579:
576:
571:
570:
539:
535:
504:
500:
473:
469:
460:
458:
450:
449:
445:
402:
398:
385:
384:
380:
373:
347:
343:
338:
331:
327:
323:
289:
285:
281:
277:
273:
269:
265:
248:
228:
216:
193:Nizhny Novgorod
189:
156:
123:
119:
96:Alma mater
91:
85:
81:
72:
59:
53:
51:
43:
31:
24:
17:
12:
11:
5:
643:
633:
632:
627:
622:
617:
612:
598:
597:
575:
574:External links
572:
569:
568:
533:
498:
487:(1): 228–259.
467:
443:
396:
378:
371:
340:
339:
337:
334:
329:
325:
321:
287:
283:
279:
275:
271:
267:
263:
247:
244:
227:
224:
215:
212:
208:A. M. Butlerov
197:Russian Empire
188:
185:
144:
143:
140:
139:
134:
128:
127:
114:
110:
109:
103:
102:
97:
93:
92:
86:
84:(aged 65)
78:
74:
73:
70:Russian Empire
60:
49:
45:
44:
41:
33:
32:
26:
25:
22:
15:
9:
6:
4:
3:
2:
642:
631:
628:
626:
623:
621:
618:
616:
613:
611:
608:
607:
605:
586:
582:
578:
577:
564:
560:
556:
552:
548:
544:
537:
529:
525:
521:
517:
513:
509:
502:
494:
490:
486:
483:(in German).
482:
478:
471:
457:
453:
447:
439:
435:
431:
427:
423:
419:
415:
411:
407:
400:
392:
388:
382:
374:
372:9780470638859
368:
364:
360:
357:: 1833–1837.
356:
352:
345:
341:
333:
318:
316:
312:
307:
303:
301:
297:
293:
261:
257:
253:
243:
241:
237:
233:
223:
221:
214:Personal life
211:
209:
205:
200:
198:
194:
184:
182:
178:
175:
171:
163:
159:
154:
150:
141:
138:
135:
133:
129:
126:
122:
118:
115:
111:
108:
104:
101:
98:
94:
89:
79:
75:
71:
67:
63:
50:
46:
39:
34:
27:
20:
589:. Retrieved
585:the original
546:
542:
536:
511:
507:
501:
484:
480:
470:
459:. Retrieved
455:
446:
413:
409:
399:
390:
381:
354:
350:
344:
319:
308:
304:
249:
229:
217:
201:
190:
153:Markownikoff
152:
148:
147:
113:Institutions
106:
82:(1904-02-11)
615:1904 deaths
610:1837 births
591:25 December
313:by finding
604:Categories
461:2021-05-19
336:References
62:Knyaginino
54:1837-12-25
563:230570680
430:1433-7851
242:in 1901.
158:‹See Tfd›
438:15221826
300:Peroxide
516:Bibcode
260:alkenes
256:halogen
220:Nikolai
177:chemist
174:Russian
162:Russian
151:, also
561:
436:
428:
369:
315:carbon
274:CHClCH
266:-CH=CH
226:Career
559:S2CID
258:) to
593:2021
434:PMID
426:ISSN
367:ISBN
246:Work
170:O.S.
77:Died
48:Born
551:doi
524:doi
489:doi
485:153
418:doi
359:doi
355:411
606::
557:.
547:60
545:.
522:.
512:83
510:.
479:.
454:.
432:.
424:.
414:43
412:.
408:.
389:.
365:.
353:.
286:CH
282:CH
195:,
164::
68:,
64:,
595:.
565:.
553::
530:.
526::
518::
495:.
491::
464:.
440:.
420::
393:.
375:.
361::
330:2
328:O
326:8
324:H
322:4
288:2
284:2
280:3
276:3
272:3
268:2
264:3
155:(
56:)
52:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
