Background
Chichibabin was born on March 19, 1871, in Kuzemin, Ukraine, the son of a lower-echelon government employee.
ul. Leninskiye Gory, 1, Moskva, Russia, 119991
Chichibabin studied at the University of Moscow from 1888 until 1892.
University Embankment, 7/9, Sankt-Peterburg, Russia, 199034
Chichibabin received his Ph.D. from the University of Saint Petersburg.
Lenin Prize
Алексе́й Чичиба́бин
Chichibabin was born on March 19, 1871, in Kuzemin, Ukraine, the son of a lower-echelon government employee.
Chichibabin studied at the University of Moscow from 1888 until 1892. From his first year there he studied under Markovnikov, investigating the reduction of propylbenzene with hydrogen iodide. He received his Ph.D. from the University of Saint Petersburg.
After graduation Chichibabin investigated privately, under the direction of M. I. Konovalov, the nitration of alkylpyridines and from then on concentrated his research on pyridine. In 1905-1906, he was an assistant professor at the University of Warsaw, and from 1909 to 1930 full professor of chemistry at Moscow Higher technical School. From 1918 to 1923 he was also a professor at the University of Moscow. In 1930, after the death of his only daughter in a chemical accident, he moved to Paris, where he worked in the organic chemistry laboratory at the College de France. His fundamental textbook, Osnovnye nachala organicheskoy khimii (Fundamentals of Organic Chemistry), has gone through seven editions since 1924 and has been translated into English, French, Spanish, Czech, Slovak, Hungarian, and Chinese.
After the beginning of World War I, Chichibabin organized the production of pharmaceuticals in Russia; he was responsible for the construction of the first Russian alkaloid plant and the production of opium, morphine, codeine, atropin, cocaine, caffeine, aspirin, phenyl salicylate, and phenacetin. In 1926 Chichibabin was the first Soviet chemist to receive the Lenin Prize, for his work with pyridines and in pharmaceutical chemistry.
Chichibabin studied naphthenic acids in Caucasian oil (he was the first to find aliphatic acids in this oil). He also worked on phenol alkylation; established the structure of musk ketone and found a new synthesis of amber musk; discovered the synthesis of thiodiglycol by the action of hydrogen sulfide on ethylene oxide; synthesized pilocarpine and santonin. In other areas of chemistry Chichibabin showed that under certain conditions organo-magnesium compounds can react with ortho esters, acetals, and even ethers. He was also concerned with triphenylmethane compounds and the theoretical problems connected with them. To explain the special properties of triarylmethyls, Chichibabin developed the concept of trivalent carbon and even attempted to explain olefins by means of it.
In pyridine chemistry, the field in which he did his most notable work, Chichibabin investigated the rearrangement of 1-benzylpyridine salts and found that they can regroup-with the benzyl radical occupying not only positions 2 and 4, previously believed, but also position 3. His studies of the reaction of aldhyde and acetylne with ammonia led to new methods of synthesizing pyridine or alkylpyridine with the alkyl group in any position. Most important is the synthesis from acetaldehyde and ammonia of 2-methyl-5-ethyl-pyridine, used for the preparation of 5-methyl-5-vinylpyridine (for copolymerization with styrine). Important methods of synthesizing furan, pyrrole, and thiphene from acetylene were also devised.
In 1913 Chichibabin discovered that a hydrogen atom in position 2 or 4 of the pyridine nucleus can be directly substituted for an amino group. Later he showed that the same was true of a hydroxyl radical. The direct amination, now known as the Chichibabin reaction, is applied to industrial preparation of 2-aminopyridine from pyridine. A study of the Chichibabin amination was extended to different pyridines, natural nicotine, and compounds of the quinoline and isoquinoline series.
Chichibabin investigated the laws governing the introduction of a second substituent into aminopyridines. A new type of amino-imino tautomerism was discovered in aminopyridines and it was shown that, depending on condiktions, alkylation can attack the amino group or the hetero-nitrogen atom. In its reactions with difunctional compounds 2-aminopyridine reacts as an amidine, forming condensed bicyclical structures.
(Fundamentals of Organic Chemistry)
1924
Chichibabin and his wife, Vera Vladmirovna Chichibabina, had one child, a daughter, Natasha, who became a chemist. She was killed by an oleum explosion in a chemical production factory in 1930.