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Alexander Borodin

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In organic chemistry , an aldehyde ( / ˈ æ l d ɪ h aɪ d / ) is an organic compound containing a functional group with the structure R−CH=O . The functional group itself (without the "R" side chain ) can be referred to as an aldehyde but can also be classified as a formyl group . Aldehydes are a common motif in many chemicals important in technology and biology.

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67-406: Alexander Porfiryevich Borodin (Russian: Александр Порфирьевич Бородин , romanized : Aleksandr Porfiryevich Borodin , IPA: [ɐlʲɪkˈsandr pɐrˈfʲi rʲjɪvʲɪtɕ bərɐˈdʲin] ; 12 November 1833 – 27 February 1887) was a Romantic composer and chemist of Georgian - Russian extraction. He was one of the prominent 19th-century composers known as " The Five ",

134-442: A native Russian keyboard layout ( JCUKEN ). In the latter case, they would type using a system of transliteration fitted for their keyboard layout , such as for English QWERTY keyboards, and then use an automated tool to convert the text into Cyrillic. There are a number of distinct and competing standards for the romanization of Russian Cyrillic , with none of them having received much popularity, and, in reality, transliteration

201-531: A 62-year-old Georgian nobleman, Luka Stepanovich Gedevanishvili, and a married 25-year-old Russian woman, Evdokia Konstantinovna Antonova. Due to the circumstances of Alexander's birth, the nobleman had him registered as the son of one of his Russian serfs , Porfiry Borodin, hence the composer's Russian last name. As a result of this registration, both Alexander and his nominal Russian father Porfiry were officially serfs of Alexander's biological father Luka. The Georgian father emancipated Alexander from serfdom when he

268-567: A Latin alphabet for the Russian language was discussed in 1929–30 during the campaign of latinisation of the languages of the USSR , when a special commission was created to propose a latinisation system for Russian. The letters of the Latin script are named in Russian as following (and are borrowed from French and/or German ): Aldehyde Aldehyde molecules have a central carbon atom that

335-592: A group dedicated to producing a "uniquely Russian" kind of classical music . Borodin is known best for his symphonies , his two string quartets , the symphonic poem In the Steppes of Central Asia and his opera Prince Igor . A doctor and chemist by profession and training, Borodin made important early contributions to organic chemistry . Although he is presently known better as a composer, he regarded medicine and science as his primary occupations, only practising music and composition in his spare time or when he

402-540: A metal catalyst. Illustrative is the generation of butyraldehyde by hydroformylation of propylene : One complication with this process is the formation of isomers, such as isobutyraldehyde: The largest operations involve methanol and ethanol respectively to formaldehyde and acetaldehyde , which are produced on multimillion ton scale annually. Other large scale aldehydes are produced by autoxidation of hydrocarbons: benzaldehyde from toluene , acrolein from propylene , and methacrolein from isobutene . In

469-480: A mixture of alcohol and carboxylic acid. Nucleophiles add readily to the carbonyl group. In the product, the carbonyl carbon becomes sp -hybridized, being bonded to the nucleophile, and the oxygen center becomes protonated: In many cases, a water molecule is removed after the addition takes place; in this case, the reaction is classed as an addition – elimination or addition – condensation reaction . There are many variations of nucleophilic addition reactions. In

536-545: A postdoctoral position at Heidelberg University . He worked in the laboratory of Emil Erlenmeyer working on benzene derivatives. He also spent time in Pisa , working on halocarbons . One experiment published during 1862 described the first nucleophilic displacement of chlorine by fluorine in benzoyl chloride . The radical halodecarboxylation of aliphatic carboxylic acids was first demonstrated by Borodin during 1861 by his synthesis of methyl bromide from silver acetate . It

603-491: A precipitate of silver, whose presence can be used to test for the presence of an aldehyde. A further oxidation reaction involves Fehling's reagent as a test. The Cu complex ions are reduced to a red-brick-coloured Cu 2 O precipitate. If the aldehyde cannot form an enolate (e.g., benzaldehyde ), addition of strong base induces the Cannizzaro reaction . This reaction results in disproportionation , producing

670-625: A precursor to acetic acid , which is now prepared by carbonylation of methanol . Many other aldehydes find commercial applications, often as precursors to alcohols, the so-called oxo alcohols , which are used in detergents. Some aldehydes are produced only on a small scale (less than 1000 tons per year) and are used as ingredients in flavours and perfumes such as Chanel No. 5 . These include cinnamaldehyde and its derivatives, citral , and lilial . The common names for aldehydes do not strictly follow official guidelines, such as those recommended by IUPAC , but these rules are useful. IUPAC prescribes

737-401: A precursor to polyurethanes . The second main aldehyde is butyraldehyde , of which about 2 500 000  tons per year are prepared by hydroformylation . It is the principal precursor to 2-ethylhexanol , which is used as a plasticizer . Acetaldehyde once was a dominating product, but production levels have declined to less than 1 000 000  tons per year because it mainly served as

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804-419: A primary or secondary amine adds to the carbonyl group and a proton is transferred from the nitrogen to the oxygen atom to create a carbinolamine . In the case of a primary amine, a water molecule can be eliminated from the carbinolamine intermediate to yield an imine or its trimer, a hexahydrotriazine This reaction is catalyzed by acid. Hydroxylamine ( NH 2 OH ) can also add to the carbonyl group. After

871-521: A professorship of chemistry at the Imperial Medical-Surgical Academy and spent the remainder of his scientific career in research, lecturing and overseeing the education of others. Eventually, he established medical courses for women in 1872. He began taking lessons in composition from Mily Balakirev during 1862. He married Ekaterina Protopopova, a pianist, during 1863, with whom he adopted several daughters. Music remained

938-600: A proper gymnasium , Borodin received good education in all of the subjects through private tutors at home. During 1850 he enrolled in the Medical–Surgical Academy in Saint Petersburg, which was later the workplace of Ivan Pavlov , and pursued a career in chemistry. On graduation he spent a year as surgeon in a military hospital, followed by three years of advanced scientific study in western Europe. During 1862, Borodin returned to Saint Petersburg to begin

1005-597: A secondary vocation for Borodin besides his main career as a chemist and physician. He suffered poor health, having overcome cholera and several minor heart failures . He died suddenly during a ball at the academy, and was interred in Tikhvin Cemetery at the Alexander Nevsky Monastery in Saint Petersburg. In his profession Borodin gained great respect, being particularly noted for his work on aldehydes . Between 1859 and 1862 Borodin had

1072-414: A sort of masked form of the parent aldehyde. For example, in aqueous solution only a tiny fraction of glucose exists as the aldehyde. Of the several methods for preparing aldehydes, one dominant technology is hydroformylation . Hydroformylation is conducted on a very large scale for diverse aldehydes. It involves treatment of the alkene with a mixture of hydrogen gas and carbon monoxide in the presence of

1139-483: A string sextet and a piano quintet. Borodin based the thematic structure and instrumental texture of his pieces on those of Felix Mendelssohn . During 1875 Borodin started his First String Quartet, much to the displeasure of Mussorgsky and Vladimir Stasov ; the other members of The Five were known to be hostile to chamber music. The First Quartet demonstrates mastery of the string quartet form. Borodin's Second Quartet , written in 1881, displays strong lyricism, as in

1206-429: Is an organic chemical compound with two aldehyde groups. The nomenclature of dialdehydes have the ending -dial or sometimes -dialdehyde . Short aliphatic dialdehydes are sometimes named after the diacid from which they can be derived. An example is butanedial , which is also called succinaldehyde (from succinic acid ). Some aldehydes are substrates for aldehyde dehydrogenase enzymes which metabolize aldehydes in

1273-415: Is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp - hybridized . The aldehyde group is somewhat polar . The C=O bond length is about 120–122 picometers . Aldehydes have properties that are diverse and that depend on the remainder of

1340-493: Is known as the aldol condensation . The Prins reaction occurs when a nucleophilic alkene or alkyne reacts with an aldehyde as electrophile. The product of the Prins reaction varies with reaction conditions and substrates employed. Aldehydes characteristically form "addition compounds" with bisulfites : This reaction is used as a test for aldehydes and is useful for separation or purification of aldehydes. A dialdehyde

1407-535: Is noted for its strong lyricism and rich harmonies. Along with some influences from Western composers, as a member of The Five, his music is also characteristic of the Russian style . His passionate music and unusual harmonies proved to have a lasting influence on the younger French composers Debussy and Ravel (in homage, the latter composed during 1913 a piano piece entitled "À la manière de Borodine"). The evocative characteristics of Borodin's music—specifically In

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1474-597: Is often carried out without any consistent standards. Scientific transliteration, also known as the International Scholarly System , is a system that has been used in linguistics since the 19th century. It is based on the Czech alphabet and formed the basis of the GOST and ISO systems. OST 8483 was the first Soviet standard on romanization of Russian, introduced on 16 October 1935. Developed by

1541-706: Is the main system of the Oxford University Press, and a variation was used by the British Library to catalogue publications acquired up to 1975. The Library of Congress system (ALA-LC) is used for newer acquisitions. The BGN/PCGN system is relatively intuitive for Anglophones to read and pronounce. In many publications, a simplified form of the system is used to render English versions of Russian names, typically converting ë to yo , simplifying -iy and -yy endings to -y , and omitting apostrophes for ъ and ь . It can be rendered using only

1608-514: The Russian language (the transliteration of Russian text from the Cyrillic script into the Latin script ), aside from its primary use for including Russian names and words in text written in a Latin alphabet, is also essential for computer users to input Russian text who either do not have a keyboard or word processor set up for inputting Cyrillic, or else are not capable of typing rapidly using

1675-440: The S. M. Kirov Military Medical Academy ), and accepted a professorship of chemistry. He worked on self- condensation of small aldehydes in a process now known as the aldol reaction , the discovery of which is jointly credited to Borodin and Charles Adolphe Wurtz . Borodin investigated the condensation of valerian aldehyde and oenanth aldehyde , which was reported by von Richter during 1869. During 1873, he described his work to

1742-512: The Swern oxidation ), or amine oxides (e.g., the Ganem oxidation ). Sterically-hindered nitroxyls (i.e., TEMPO ) can catalyze aldehyde formation with a cheaper oxidant . Alternatively, vicinal diols or their oxidized sequelae ( acyloins or α-hydroxy acids ) can be oxidized with cleavage to two aldehydes or an aldehyde and carbon dioxide . Aldehydes participate in many reactions. From

1809-564: The Wacker process , oxidation of ethylene to acetaldehyde in the presence of copper and palladium catalysts, is also used. " Green " and cheap oxygen (or air) is the oxidant of choice. Laboratories may instead apply a wide variety of specialized oxidizing agents , which are often consumed stoichiometrically. chromium(VI) reagents are popular . Oxidation can be achieved by heating the alcohol with an acidified solution of potassium dichromate . In this case, excess dichromate will further oxidize

1876-411: The acetalisation reaction, under acidic or basic conditions, an alcohol adds to the carbonyl group and a proton is transferred to form a hemiacetal . Under acidic conditions, the hemiacetal and the alcohol can further react to form an acetal and water. Simple hemiacetals are usually unstable, although cyclic ones such as glucose can be stable. Acetals are stable, but revert to the aldehyde in

1943-543: The silver-mirror test . In this test, an aldehyde is treated with Tollens' reagent , which is prepared by adding a drop of sodium hydroxide solution into silver nitrate solution to give a precipitate of silver(I) oxide, and then adding just enough dilute ammonia solution to redissolve the precipitate in aqueous ammonia to produce [Ag(NH 3 ) 2 ] complex. This reagent converts aldehydes to carboxylic acids without attacking carbon–carbon double bonds. The name silver-mirror test arises because this reaction produces

2010-850: The Bolshoi State Opera and Ballet Company in Russia during 2013, and one at the Metropolitan Opera Company of New York City during 2014. No other member of the Balakirev circle identified himself so much with absolute music as did Borodin in his two string quartets, in addition to his many earlier chamber compositions. As a cellist, he was an enthusiastic chamber music player, an interest that increased during his chemical studies in Heidelberg between 1859 and 1861. This early period yielded, among other chamber works,

2077-456: The British Library since 1975. The formal, unambiguous version of the system for bibliographic cataloguing requires some diacritics, two-letter tie characters , and prime marks. The standard is also often adapted as a "simplified" or "modified Library of Congress system" for use in text for a non-specialized audience, omitting the special characters and diacritics, simplifying endings, and modifying iotated initials. British Standard 2979:1958

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2144-761: The HCN molecule, to form the alcohol group of the cyanohydrin. Organometallic compounds , such as organolithium reagents , Grignard reagents , or acetylides , undergo nucleophilic addition reactions, yielding a substituted alcohol group. Related reactions include organostannane additions , Barbier reactions , and the Nozaki–Hiyama–Kishi reaction . In the aldol reaction , the metal enolates of ketones , esters , amides , and carboxylic acids add to aldehydes to form β-hydroxycarbonyl compounds ( aldols ). Acid or base-catalyzed dehydration then leads to α,β-unsaturated carbonyl compounds. The combination of these two steps

2211-542: The Latin Alphabet is an adoption of ISO 9:1995 . It is the official standard of both Russia and the Commonwealth of Independent States (CIS). GOST 52535.1-2006 Identification cards. Machine readable travel documents. Part 1. Machine readable passports is an adoption of an ICAO standard for travel documents. It was used in Russian passports for a short period during 2010–2013 ( see below ). The standard

2278-685: The National Administration for Geodesy and Cartography at the USSR Council of Ministers , GOST 16876-71 has been in service since 1973. Replaced by GOST 7.79-2000. This standard is an equivalent of GOST 16876-71 and was adopted as an official standard of the COMECON . GOST 7.79-2000 System of Standards on Information, Librarianship, and Publishing–Rules for Transliteration of the Cyrillic Characters Using

2345-729: The Russian Chemical Society and noted similarities with compounds recently reported by Wurtz. He published his last full article during 1875 on reactions of amides and his last publication concerned a method for the identification of urea in animal urine. His successor as chemistry professor of the Medical-Surgical academy was his son-in-law and fellow chemist, Aleksandr Dianin . Borodin met Mily Balakirev during 1862. While under Balakirev's tutelage in composition he began his Symphony No. 1 in E-flat major; it

2412-503: The Steppes of Central Asia , his Symphony No. 2 , Prince Igor – made possible the adaptation of his compositions in the 1953 musical Kismet , by Robert Wright and George Forrest , notably in the songs " Stranger in Paradise ", " And This Is My Beloved " and " Baubles, Bangles, & Beads ". In 1954, Borodin was posthumously awarded a Tony Award for this show. Sources Romanization of Russian The romanization of

2479-478: The aldehyde to a carboxylic acid , so either the aldehyde is distilled out as it forms (if volatile ) or milder reagents such as PCC are used. A variety of reagent systems achieve aldehydes under chromium-free conditions. One such are the hypervalent organoiodine compounds (i.e., IBX acid , Dess–Martin periodinane ), although these often also oxidize the α position . A Lux-Flood acid will activate other pre-oxidized substrates: various sulfoxides (e.g.

2546-505: The barbarous Polovtsians by travelling eastward across the Steppes. The Polovtsians were apparently a nomadic tribe originally of Turkic origin who habitually attacked southern Russia. A full solar eclipse early during the first act foreshadows an ominous outcome to the invasion. Prince Igor's troops are defeated. The story tells of the capture of Prince Igor, and his son, Vladimir, of Russia by Polovtsian chief Khan Konchak, who entertains his prisoners lavishly and orders his slaves to perform

2613-622: The basic letters and punctuation found on English-language keyboards: no diacritics or unusual letters are required, although the interpunct character (·) may be used to avoid ambiguity. This particular standard is part of the BGN/PCGN romanization system which was developed by the United States Board on Geographic Names and by the Permanent Committee on Geographical Names for British Official Use . The portion of

2680-447: The body. There are toxicities associated with some aldehydes that are related to neurodegenerative disease, heart disease , and some types of cancer . Of all aldehydes, formaldehyde is produced on the largest scale, about 6 000 000  tons per year . It is mainly used in the production of resins when combined with urea , melamine , and phenol (e.g., Bakelite ). It is a precursor to methylene diphenyl diisocyanate ("MDI"),

2747-486: The carbonyl group to form cyanohydrins , R−CH(OH)CN . In this reaction the CN ion is the nucleophile that attacks the partially positive carbon atom of the carbonyl group . The mechanism involves a pair of electrons from the carbonyl-group double bond transferring to the oxygen atom, leaving it single-bonded to carbon and giving the oxygen atom a negative charge. This intermediate ion rapidly reacts with H , such as from

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2814-407: The corresponding carboxyl group ( −COOH ). The preferred oxidant in industry is oxygen or air. In the laboratory, popular oxidizing agents include potassium permanganate , nitric acid , chromium(VI) oxide , and chromic acid . The combination of manganese dioxide , cyanide , acetic acid and methanol will convert the aldehyde to a methyl ester . Another oxidation reaction is the basis of

2881-462: The dominant tautomer in strong acid or base solutions, and enolized aldehydes undergo nucleophilic attack at the α position . The formyl group can be readily reduced to a primary alcohol ( −CH 2 OH ). Typically this conversion is accomplished by catalytic hydrogenation either directly or by transfer hydrogenation . Stoichiometric reductions are also popular, as can be effected with sodium borohydride . The formyl group readily oxidizes to

2948-493: The elimination of water, this results in an oxime . An ammonia derivative of the form H 2 NNR 2 such as hydrazine ( H 2 NNH 2 ) or 2,4-dinitrophenylhydrazine can also be the nucleophile and after the elimination of water, resulting in the formation of a hydrazone , which are usually orange crystalline solids. This reaction forms the basis of a test for aldehydes and ketones . The cyano group in HCN can add to

3015-412: The famous 'Polovtsian Dances', which provide a thrilling climax to the second act. The second half of the opera finds Prince Igor returning to his homeland, but rather than finding himself in disgrace, he is welcomed home by the townspeople and by his wife, Yaroslavna. Although for a while rarely performed in its entirety outside of Russia, this opera has received two notable new productions recently, one at

3082-551: The flavorant cinnamaldehyde , (7) retinal , which forms with opsins photoreceptors , and (8) the vitamin pyridoxal . Traces of many aldehydes are found in essential oils and often contribute to their pleasant odours, including cinnamaldehyde , cilantro , and vanillin . Possibly due to the high reactivity of the formyl group, aldehydes are not commonly found in organic "building block" molecules, such as amino acids, nucleic acids, and lipids. However, most sugars are derivatives of aldehydes. These aldoses exist as hemiacetals ,

3149-453: The following nomenclature for aldehydes: The word aldehyde was coined by Justus von Liebig as a contraction of the Latin al cohol dehyd rogenatus (dehydrogenated alcohol). In the past, aldehydes were sometimes named after the corresponding alcohols , for example, vinous aldehyde for acetaldehyde . ( Vinous is from Latin vinum "wine", the traditional source of ethanol , cognate with vinyl .) The term formyl group

3216-413: The industrial perspective, important reactions are: Because of resonance stabilization of the conjugate base, an α-hydrogen in an aldehyde is weakly acidic with a p K a near 17. Note, however, this is much more acidic than an alkane or ether hydrogen, which has p K a near 50 approximately, and is even more acidic than a ketone α-hydrogen which has p K a near 20. This acidification of

3283-496: The introduction of a dedicated Latin alphabet for writing the Russian language. Such an alphabet would not necessarily bind closely to the traditional Cyrillic orthography. The transition from Cyrillic to Latin has been proposed several times throughout history (especially during the Soviet era), but was never conducted on a large scale, except for informal romanizations in the computer era. The most serious possibility of adoption of

3350-403: The molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are soluble in water, and the volatile aldehydes have pungent odors. Aldehydes can be identified by spectroscopic methods. Using IR spectroscopy , they display a strong ν CO band near 1700 cm . In their H NMR spectra, the formyl hydrogen center absorbs near δ H  9.5 to 10, which is a distinctive part of

3417-582: The most important historical Russian operas. It contains the Polovtsian Dances , often performed as a stand-alone concert work forming what is probably Borodin's best-known composition. Borodin left the opera (and a few other works) incomplete at his death. Prince Igor was completed posthumously by Rimsky-Korsakov and Alexander Glazunov . It is set in the 12th century, when the Russians, commanded by Prince Igor of Seversk, determined to conquer

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3484-484: The new system and the old one, citizens who wanted to retain the old version of a name's transliteration, especially one that had been in the old pre-2010 passport, could apply to the local migration office before they acquired a new passport. The standard was abandoned in 2013. In 2013, Order No. 320 of the Federal Migration Service of Russia came into force. It states that all personal names in

3551-509: The passports must be transliterated by using the ICAO system , which is published in Doc 9303 " Machine Readable Travel Documents, Part 3 ". The system differs from the GOST R 52535.1-2006 system in two things: ц is transliterated into ts (as in pre-2010 systems), ъ is transliterated into ie (a novelty). In a second sense, the romanization or Latinization of Russian may also indicate

3618-441: The popular symphonic poem In the Steppes of Central Asia . Two years later he began composing a third symphony, but left it unfinished at his death; two movements of it were later completed and orchestrated by Alexander Glazunov . During 1868, Borodin became distracted from initial work on the second symphony by preoccupation with the opera Prince Igor , which is considered by some to be his most significant work and one of

3685-422: The presence of acid. Aldehydes can react with water to form hydrates , R−CH(OH) 2 . These diols are stable when strong electron withdrawing groups are present, as in chloral hydrate . The mechanism of formation is identical to hemiacetal formation. Another aldehyde molecule can also act as the nucleophile to give polymeric or oligomeric acetals called paraldehydes. In alkylimino-de-oxo-bisubstitution ,

3752-562: The spectrum. This signal shows the characteristic coupling to any protons on the α carbon with a small coupling constant typically less than 3.0 Hz. The C NMR spectra of aldehydes and ketones gives a suppressed (weak) but distinctive signal at δ C  190 to 205. Important aldehydes and related compounds. The aldehyde group (or formyl group ) is colored red. From the left: (1) formaldehyde and (2) its trimer 1,3,5-trioxane , (3) acetaldehyde and (4) its enol vinyl alcohol , (5) glucose (pyranose form as α- D -glucopyranose), (6)

3819-502: The system pertaining to the Russian language was adopted by BGN in 1944 and by PCGN in 1947. In Soviet international passports , transliteration was based on French rules but without diacritics and so all names were transliterated in a French-style system . In 1997, with the introduction of new Russian passports , a diacritic-free English-oriented system was established by the Russian Ministry of Internal Affairs , but

3886-447: The system was also abandoned in 2010. In 2006, GOST R 52535.1-2006 was adopted, which defines technical requirements and standards for Russian international passports and introduces its own system of transliteration. In 2010, the Federal Migration Service of Russia approved Order No. 26, stating that all personal names in the passports issued after 2010 must be transliterated using GOST R 52535.1-2006. Because of some differences between

3953-825: The third movement's popular " Nocturne ." While the First Quartet is richer in changes of mood, the Second Quartet has a more uniform atmosphere and expression. Borodin's fame outside the Russian Empire was made possible during his lifetime by Franz Liszt , who arranged a performance of the Symphony No. 1 in Germany during 1880, and by the Comtesse de Mercy-Argenteau in Belgium and France. His music

4020-671: The use of diacritics) that faithfully represents the original and allows for reverse transliteration for Cyrillic text in any contemporary language. The UNGEGN , a Working Group of the United Nations , in 1987 recommended a romanization system for geographical names, which was based on the 1983 version of GOST 16876-71 . It may be found in some international cartographic products. American Library Association and Library of Congress (ALA-LC) romanization tables for Slavic alphabets are used in North American libraries and in

4087-467: The α-hydrogen in aldehyde is attributed to: The formyl proton itself does not readily undergo deprotonation. Aldehydes (except those without an alpha carbon, or without protons on the alpha carbon, such as formaldehyde and benzaldehyde) can exist in either the keto or the enol tautomer . Keto–enol tautomerism is catalyzed by either acid or base. In neutral solution, the enol is the minority tautomer, reversing several times per second. But it becomes

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4154-552: Was Heinz Hunsdiecker and his wife Cläre , however, who developed Borodin's work into a general method, for which they were granted a US patent during 1939, and which they published in the journal Chemische Berichte during 1942. The method is generally known as either the Hunsdiecker reaction or the Hunsdiecker–;Borodin reaction. During 1862, Borodin returned to the Medical–Surgical Academy (now known as

4221-434: Was 7 years old and provided housing and money for him and his mother. Despite this, Alexander was never publicly recognized by his mother, who was referred to by young Borodin as his "aunt". Despite his status as a commoner, Borodin was well provided for by his Georgian father and grew up in a large four-storey house, which was gifted to Alexander and his "aunt" by the nobleman. Although his registration prevented enrollment in

4288-470: Was first performed during 1869, with Balakirev conducting. During that same year Borodin started on his Symphony No. 2 in B minor, which was not particularly successful at its premiere during 1877 under Eduard Nápravník , but with some minor re-orchestration received a successful performance during 1879 by the Free Music School under Nikolai Rimsky-Korsakov 's direction. During 1880 he composed

4355-561: Was ill. As a chemist, Borodin is known best for his work concerning organic synthesis , including being among the first chemists to demonstrate nucleophilic substitution , as well as being the co-discoverer of the aldol reaction . Borodin was a promoter of education in Russia and founded the School of Medicine for Women in Saint Petersburg, where he taught until 1885. Borodin was born in Saint Petersburg as an illegitimate son of

4422-519: Was substituted in 2013 by GOST R ISO/ IEC 7501-1-2013, which does not contain romanization, but directly refers to the ICAO romanization ( see below ). Names on street and road signs in the Soviet Union were romanized according to GOST 10807-78 (tables 17, 18), which was amended by newer Russian GOST R 52290-2004 (tables Г.4, Г.5), the romanizations in both the standards are practically identical. ISO/R 9, established in 1954 and updated in 1968,

4489-570: Was the adoption of the scientific transliteration by the International Organization for Standardization (ISO). It covers Russian and seven other Slavic languages. ISO 9:1995 is the current transliteration standard from ISO. It is based on its predecessor ISO/R 9:1968, which it deprecates; for Russian, the two are the same except in the treatment of five modern letters. ISO 9:1995 is the first language-independent, univocal system of one character for one character equivalents (by

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