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organic chemistry,branch of chemistrychemistry,
branch of science concerned with the properties, composition, and structure of substances and the changes they undergo when they combine or react under specified conditions.
..... Click the link for more information. dealing with the compounds of carbon. While it is only the fourteenth most common element on earth, carbon forms by far the greatest number of different compounds. Organic chemistry is of vital importance to the petrochemical, pharmaceutical, and textile industries, where a prime concern is the synthesis of new organic molecules and polymerspolymer
, chemical compound with high molecular weight consisting of a number of structural units linked together by covalent bonds (see chemical bond). The simple molecules that may become structural units are themselves called monomers; two monomers combine to form a dimer,
..... Click the link for more information. . Compounds containing only hydrogen and carbon, of which there are many thousands, are called hydrocarbonshydrocarbon
, any organic compound composed solely of the elements hydrogen and carbon. The hydrocarbons differ both in the total number of carbon and hydrogen atoms in their molecules and in the proportion of hydrogen to carbon.
..... Click the link for more information. ; the simplest is methanemethane
, CH4, colorless, odorless, gaseous saturated hydrocarbon; the simplest alkane. It is less dense than air, melts at −184°C;, and boils at −161.4°C;. It is combustible and can form explosive mixtures with air.
..... Click the link for more information. (CH4). In general, a particular type of organic compound, such as an alcoholalcohol,
any of a class of organic compounds with the general formula R-OH, where R represents an alkyl group made up of carbon and hydrogen in various proportions and -OH represents one or more hydroxyl groups.
..... Click the link for more information. , aldehydealdehyde
[alcohol + New Lat. dehydrogenatus=dehydrogenated], any of a class of organic compounds that contain the carbonyl group, , and in which the carbonyl group is bonded to at least one hydrogen; the general formula for an aldehyde is RCHO, where R is hydrogen
..... Click the link for more information. , etherether,
any of a number of organic compounds whose molecules contain two hydrocarbon groups joined by single bonds to an oxygen atom. The most common of these compounds is ethyl ether, CH3CH2OCH2CH3
..... Click the link for more information. , or ketoneketone
, any of a class of organic compounds that contain the carbonyl group, C=O, and in which the carbonyl group is bonded only to carbon atoms. The general formula for a ketone is RCOR′, where R and R′ are alkyl or aryl groups.
..... Click the link for more information. , is identified by the presence of a characteristic functional groupfunctional group,
in organic chemistry, group of atoms within a molecule that is responsible for certain properties of the molecule and reactions in which it takes part. Organic compounds are frequently classified according to the functional group or groups they contain.
..... Click the link for more information. of atoms. The functional group is the part of the molecule most responsible for its particular chemical nature. Organic compounds containing nitrogen are of great importance in biochemistrybiochemistry,
science concerned chiefly with the chemistry of biological processes; it attempts to utilize the tools and concepts of chemistry, particularly organic and physical chemistry, for elucidation of the living system.
..... Click the link for more information. . They generally contain the amine group (NH2). Molecules containing both the NH2 and COOH groups are called amino acidsamino acid
, any one of a class of simple organic compounds containing carbon, hydrogen, oxygen, nitrogen, and in certain cases sulfur. These compounds are the building blocks of proteins.
..... Click the link for more information. and are the building blocks of proteins.
a branch of chemistry; a natural-science discipline that studies compounds of carbon with other elements, which are called organic compounds, as well as the laws of transformation of such compounds.
Carbon forms compounds with most elements and has the most pronounced capacity—relative to other elements—for forming chain or cyclical molecules. The backbone of such molecules may consist of a virtually unlimited number of carbon atoms bound directly to one another, or it may include atoms of other elements in addition to carbon. The phenomenon most characteristic of carbon compounds is isomerism, that is, the existence of compounds of identical composition and molecular mass but with a different sequence of linkage or spatial arrangement of the atoms and, as a result, different chemical and physical properties. Because of this, the number of organic compounds is extremely great; by the 1970’s, more than 3 million organic compounds were known. By contrast, slightly more than 100,000 compounds of all other elements have been identified.
Organic compounds are capable of complex and diverse transformations, which differ significantly from the transformations of inorganic compounds and play the major role in the formation and activity of plant and animal organisms. Among the organic compounds are carbohydrates and proteins, which are associated with metabolism; hormones, which regulate metabolism; nucleic acids, which carry the genetic code of an organism; and vitamins. Organic chemistry is thus a unique bridge between the sciences studying inanimate matter and the highest form of the existence of matter—life. Many phenomena and regularities of chemistry, such as isomerism, were discovered in the study of organic compounds.
Classification of organic compounds. All organic compounds are subdivided into three major classes: acyclic, carbocyclic (or isocyclic), and heterocyclic.
Compounds of the first class (fatty, or aliphatic, compounds) include hydrocarbons and their open-chain derivatives: the homologous series of methane hydrocarbons, which is also called the alkane series, and the homologous series of unsaturated hydrocarbons, such as ethylene (alkenes), acetylene (alkynes), and dienes. The carbocyclic compounds include hydrocarbons and their derivatives that contain rings of carbon atoms in the molecule, such as hydrocarbons and their derivatives of the cycloparaffin series; cyclic unsaturated compounds; and aromatic hydrocarbons and their derivatives that contain benzene rings (also, in particular, polycyclic aromatic compounds such as naphthalene and anthracene). The heterocyclic compounds include organic compounds whose molecules have rings containing atoms of oxygen, nitrogen, sulfur, phosphorus, arsenic, or other elements in addition to carbon atoms.
Each hydrocarbon can form a set of derivatives; representatives of such derivatives are formally produced by substitution of a hydrogen atom in the hydrocarbon by some functional group, which determines the chemical properties of the compound. Thus, the derivatives of methane, CH4, include methyl chloride, CH3Cl; methanol, CH3OH; methylamine, CH3NH2; and nitromethane, CH3NO2. Analogously, the derivatives of benzene, C6H6, include chlorobenzene, C6H5Cl; phenol, C6H5OH; aniline, C6H5NH2; and nitrobenzene, C6H5NO2. Identically substituted derivatives of homologous hydrocarbons also form homologous series of derivatives including halogen-containing compounds, alcohols, amines, and nitro compounds. (For names of chemical compounds, See, .)
History. The origins of organic chemistry lie in remote antiquity; even then the fermentation of ethyl alcohol, or ethanol, and acetic acid and dyeing with indigo and alizarin were known. However, even in the Middle Ages (the period of alchemy), only a few organic compounds were known. All research in that period was concerned with developing operations through which, it was thought, certain simple substances could be transformed into others. Beginning in the 16th century (the period of iatrochemistry), research was directed largely toward the isolation and use of various medicinal preparations. A number of essential oils were isolated from plants, and diethyl ether was prepared. Methanol and acetic acid were obtained by dry distillation of wood, and tartaric acid was obtained by dry distillation of potassium bitartrate. Acetic acid was obtained by distillation of lead acetate, and succinic acid by distillation of amber.
A great role in the development of organic chemistry belongs to A. Lavoisier, who developed the fundamental quantitative methods for determining the composition of chemical compounds. The methods were subsequently improved by L. Thénard, J. Berzelius, J. von Liebig, and J. Dumas. The principles of these methods—combustion of weighed samples of a compound in an oxygen atmosphere, with subsequent capture and weighing of the products of combustion, CO2 and H2O—are the basis of modern elemental analysis, including microanalysis. As a result of the analysis of a large number of compounds, the previously prevailing notion of a fundamental difference between compounds of plant and animal origin gradually disappeared.
The term “organic compounds” was first encountered toward the end of the 18th century. The term “organic chemistry” was introduced by Berzelius in 1827 in the first manual on organic chemistry, which he wrote. The phenomenon of isomerism was discovered by F. Wöhler and Liebig in 1822–23. The first synthesis of an organic compound was achieved by Wöhler, who obtained oxalic acid from cyanogen in 1824 and urea by heating ammonium cyanate in 1828.
Beginning in the mid-19th century, the number of organic compounds obtained by synthesis increased rapidly. In 1842, N. N. Zinin obtained aniline by reduction of nitrobenzene, and in 1845, A. Kolbe synthesized acetic acid. P. Berthelot synthesized analogues of natural fats in 1854. In 1861, A. M. Butlerov obtained the first synthetic sugary substance, which he called metilenitan and from which acrose was later isolated. Synthetic organic chemistry acquired increasing importance. As a result of the successes in synthesis, the prevalent idealistic view of the necessity of a “vital force” for the production of organic compounds was discredited.
The development of theoretical concepts in organic chemistry began in the second quarter of the 19th century, when the radical theory was advanced by Liebig, Wöhler, E. Frankland, and R. von Bunsen. The basis of the theory—the hypothesis that groups of atoms, or radicals, pass unchanged from one compound to another—remains valid in many cases. Many physical and chemical methods for the study of compounds of unknown structure have been based on this hypothesis. Later (1834–39), Dumas showed the possibility of replacing the positively charged atoms in a radical with electronegative atoms without serious changes in the electrochemical nature of the radical, which had been considered impossible until Dumas’s studies.
The theory of types (1848–51, 1853), which was developed by Dumas, C. Gerhardt, and A. Laurent, replaced the radical theory. Dumas, Gerhardt, and Laurent succeeded in classifying organic compounds in terms of types of simple inorganic compounds. Thus, alcohols were considered compounds of the water type; amines, compounds of the ammonia type; and alkyl halides, compounds of the hydrogen chloride type. Later, F. A. Kekulé proposed a fourth type, the methane type, from which he produced all the hydrocarbons. The theory of types makes possible the precise classification of organic compounds that is the basis of the modern classification of organic compounds. However, the theory sought only to explain the reactivity of organic compounds and discounted the basic possibility of knowing the structure of the compounds. In 1853, Frankland, while studying organometallic compounds, introduced the concept of valence. In 1857, Kekulé proposed the possibility that carbon atoms are linked to one another and proved that carbon exists in the tetravalent state. In 1858, A. Couper, using the valence rule and Kekulé’s hypothesis on the linkage of carbon atoms, was the first to depart from the theory of types; he wrote formulas for organic compounds that were very similar to the modern formulas. However, the ideas of the theory of types remained very strong, and the development of theory continued to lag behind experimental progress.
In 1861, Butlerov proposed the structural theory of organic compounds. He introduced several new concepts into organic chemistry: the chemical bond, the bonding order of atoms in a molecule, and the interaction of atoms that are directly bonded to one another or are not bonded. Butlerov’s structural theory brilliantly explained cases of isomerism that were known at the time but were not understood. In 1864, Butlerov predicted the possibility of isomerism in hydrocarbons and in 1867 confirmed his prediction by the synthesis of isobutane. The integral theory developed by Butlerov is the basis for modern concepts of the chemical structure of organic compounds. One of the most important tenets of structural theory, the idea of interaction of atoms, was later developed by V. V. Markovnikov. Detailed study of this action facilitated further development of the structural theory and concepts of the distribution of electron density and the reactivity of organic compounds.
In 1869, J. Wislicenus showed that isomerism is also observed for completely identical sequences of atoms in a molecule. He proved the identity of the structures of lactic and sarcolactic acids and concluded that the fine differences in the properties of molecules with identical structure should be sought in a difference in the spatial arrangement of the atoms. In 1874, J. van’t Hoff and the French chemist J. Le Bel proposed the theory of the spatial arrangement of atoms in molecules, or stereochemistry. According to van’t Hoff, this theory is based on the notion of a tetrahedral model of tetravalent carbon and the premise that optical isomerism is the consequence of the spatial asymmetry of molecules, in which the carbon atom is attached to four different substituents. Van’t Hoff also expressed a hypothesis on the possibility of another type of spatial isomerism in molecules lacking an asymmetric carbon atom. Wislicenus soon proved that fumaric acid, which had previously been considered a polymer of maleic acid, was actually a geometric isomer of maleic acid (geometric, or cis-trans, isomerism). It is clear that the stereochemical approach could be founded only on concepts of molecular structure as understood by Butlerov.
By the end of the 19th century, much factual material had been accumulated, including material on aromatic compounds. In particular, the chemistry of benzene, a substance discovered by M. Faraday in 1825, was widely studied. In 1865, Kekulé proposed the first benzene theory of the structure of aromatic compounds, which assumed that carbon atoms in organic compounds may form rings. According to the theory, benzene has a symmetrical structure because of the cyclic structure of methine CH groups linked alternately by single and double bonds. However, the benzene structure according to Kekulé should admit the existence of two ortho-substituted homologues or derivatives of benzene, which were not observed. The resistance of benzene to strong oxidizing agents, as well as several other “aromatic” properties of benzene and its derivatives, also ran counter to the proposed formula. Therefore, in 1872, Kekulé introduced the concept of exchange (rapid shifting) of single and double bonds and eliminated the formal differences between the two ortho- positions. Although the structure of benzene according to Kekulé contradicted the substance’s known physical and chemical properties, it was long accepted by the vast majority of chemists without any changes. Thus, a number of problems remained unsolved from the viewpoint of “classical” structural theory. These problems also related to the uniqueness of the properties of many other compounds with conjugated systems of bonds. The structure of benzene and other aromatic systems could be established only with the advent of physical methods of research and with the development of quantum-chemical concepts of the structure of organic compounds.
Electron concepts advanced by W. Kossel and G. Lewis in 1916 gave physical significance to the concept of the chemical bond, a pair of shared electrons. However, in the form in which the ideas were formulated, they could not reflect the fine transitions from covalent to ionic bonds, to a great extent remaining formal. Only with the aid of quantum chemistry did fundamentally new substantiation of the basically correct idea of the electron theory become possible.
Lewis’ ideas on the pair of electrons that form the bond and are strictly localized on that bond proved only approximate and cannot be adopted in most cases.
Modern concepts in structural theory; significance of organic chemistry. Consideration of the quantum properties of the electron and the concept of electron density and the interaction of electrons in conjugated systems opened up new possibilities for the study of the structure and interactions of atoms in the molecule and the reactivity of organic compounds. In alkanes, single C—C bonds, or σ-bonds, are actually formed by an electron pair; in symmetrical hydrocarbons, the electron density in the space between the bonded carbon atoms is greater than the sum of the corresponding electron densities of the same atoms when isolated and is symmetrically distributed relative to the axis joining the centers of the atoms. The increase in electron density results from the overlapping of the electron clouds of the atoms along a line joining the atoms’ centers.
In asymmetric paraffins, incomplete symmetry in the distribution of electron density becomes possible. However, this asymmetry is so insignificant that dipole moments are hardly ever found for paraffin hydrocarbons. The same behavior is true for unsaturated hydrocarbons such as ethylene and butadiene, in which the carbon atoms are bonded to one another by a double bond: a σ- and π-bond. The introduction of an electron-donor methyl group into these molecules leads to a shift in electron density toward the terminal carbon atom as a result of the high polarizability of the π-bond, and propylene (I) has a dipole moment of 0.35 debye, whereas 1-methylbutadiene has a dipole moment of 0.68 debye. The distribution of electron density in these cases is usually represented by one of the following diagrams:
(the signs δ+ and δ– indicate partial charges on the carbon atoms).
Several empirical rules of organic chemistry fit well into the notion of the distribution of electron density. Thus, it follows from the formula for propylene given above that, upon heterolytic addition of a hydrogen halide to the compound, the proton should attach itself at the site of greatest electron density—that is, at the least substituted carbon atom (the Markovnikov rule).
The introduction into hydrocarbons of atoms or groups whose electronegativity differs strongly from that of carbon or hydrogen atoms has a much greater effect. For example, the introduction of an electrophilic substituent into hydrocarbons leads to a change in the mobility of hydrogen atoms in the C—H and O—H bonds. A similar type of interaction of atoms, which is also explained by change in the electron density, attenuates rapidly in saturated compounds and is transmitted almost without attenuation along a chain of conjugated bonds.
A distinction is usually made between two types of substituent effects: the inductive effect along σ-bond chains and the conjugation effect along chains with conjugated bonds. Thus, the increase in acidity of chloroacetic acid (II) relative to acetic acid, CH3COOH, is explained by the inductive effect of the chlorine atom, whereas the lability of the hydrogen atoms of the methyl groups in acetaldehyde (III) or sorbaldehyde (IV) is explained by the conjugation effect:
The redistribution of electron density, particularly at the instant of reaction, occurs not only in bonds that are affected by the reaction but also in other parts of the molecule. The apparent abnormality of salt formation of p-dimethylaminoazobenzene (V), with the localization of a proton on the weakly basic nitrogen of the azo group, is explained by the shift of the reaction center of the molecule, because of a displacement of electron density at the instant of reaction, in the direction indicated by the arrows:
The effect of conjugation is also evident in cases when the two possible directions of a reaction of organic compounds are not due to tautomerism. Thus, alkylation of sodium enolates at the carbon atom occurs as a result of a shift of the reaction center caused by conjugation of the bonds:
The interaction of atoms as a result of the conjugation of bonds also appears in aromatic compounds. In the case of electrophilic substitution, electron-donor (nucleophilic) substituents (VI) orient to the ortho- and para- positions, and electron-acceptor (electrophilic) substituents (VII) orient to the meta- position:
Thus, the various processes of organic chemistry have found a natural explanation in terms of modern quantum-chemical concepts. The theoretical concepts of organic chemistry have been strengthened and have acquired predictive capacities.
As a result of the development of theoretical and physical research methods, the problem of the structure of aromatic systems, including the structure of benzene, has been definitively solved. The structure of benzene is described as follows: the six carbon atoms of the benzene ring are located in a single plane and are linked by σ-bonds, whereas the six π-electrons make up a single labile electron system. The complete equality of the C—C bonds, which has been confirmed by experiment, and the high symmetry of benzene with a sixfold axis are a consequence of the benzene structure. From this it follows that benzene is nonpolar and has anisotropic diamagnetic susceptibility. Analogous properties are characteristic of all aromatic systems in which the number of π-electrons is equal to 4n + 2 (the Hückel rule). Benzene is far from the only example of compounds with equalized double and single bonds; analogous equalizing is observed for tropolone, tropylium bromide, ferrocene, and diphenylpolyenes. It has not been possible to develop a completely satisfactory graphic representation of the structure of benzene and other aromatic compounds. Such compounds are described by a set of valence diagrams (VIII), first proposed by L. Pauling in his theory of resonance, or the system (IX) in which the curved arrows also show the equality of the bonds (first used in the theory of resonance):
The same representations are used for graphic interpretation of the equal distribution of the electron density in symmetric ions, such as the carboxylate anion (X and XI, respectively); they are also used in explaining the weak basicity of amides (XII and XIII):
Organic chemistry entered a new phase in the mid-20th century. Many areas of organic chemistry developed so intensively that they formed large specialized divisions, such as stereochemistry, polymer chemistry, and the chemistry of natural substances, antibiotics, vitamins, hormones, organometallic compounds, organofluoric compounds, and dyes.
Rapid structural analysis of complex organic compounds and the quick solution of many important problems have been made possible by progress in the theory and development of various physical research methods, such as X-ray crystallographic structural analysis, ultraviolet and infrared spectroscopy, Raman spectroscopy, nuclear magnetic resonance, chemically induced dynamic nuclear polarization, and mass spectrometry. Chromatographic methods for the identification and segregation of various compounds are also of importance in this regard. The use of physical methods in the study of the kinetics of reactions of organic compounds makes possible the study of reactions with half-lives of 10–8 to 10–9 sec. Correlation equations based on the principle of linearity of free energy make possible qualitative evaluation of the relationships between the structure and reactivity of organic compounds, even those that are physiologically active.
Organic chemistry is closely linked to allied natural sciences—biochemistry, medicine, and biology. To a significant extent, the application of the ideas and methods of organic chemistry in these sciences has resulted in the development of a new scientific discipline, molecular biology.
The methods of organic chemistry, along with physical research methods, have played an important role in establishing the structure of the nucleic acids and many proteins and complex natural compounds; they have also been used to elucidate the mechanism and regulation of protein synthesis. The capacity of organic chemistry for synthesis has grown greatly and has led to the synthesis of such complex natural compounds as chlorophyll and vitamin B12 (R. Woodward) and polynucleotides with a specific ordering of component units (A. Todd and H. G. Khorana). The development of automated synthesis of many polypeptides, including enzymes, represented a great success of the methods of synthesis.
A new class of organic compounds has been synthesized; the compounds are formed by the interweaving of two or more cyclic molecules similar to an ordinary chain (catenanes, XIV) or to barbells with rings on their axes (rotaxanes, XV):
The individual segments of the molecules are bound by mechanical forces.
The synthesis of a gene, which was accomplished by Khorana and his co-workers (1967–70), may be considered the most significant achievement of synthetic organic chemistry.
The methods of organic chemistry have acquired great importance in modern technology for the production of synthetic rubbers, plastics, synthetic fibers, dyes, medicines, still and motion-picture film, plant growth factors, and pesticides. Advances in organic chemistry in the areas of industrial organic synthesis and petrochemical synthesis have not only changed the technology of a number of industries but have also led to the introduction of new types of production. As a result of the establishment of the relationships between the structure and properties of organic compounds, the creation of new materials for various purposes, with predetermined properties, has become possible. Organic chemistry has attained a level that corresponds to its important role in the creation of the material culture of modern society.
Scientific institutions and organizations; periodical publications. In the USSR, scientific work in organic chemistry is conducted at research institutes of the Academy of Sciences of the USSR, such as the N. D. Zelinskii Institute of Organic Chemistry, the A. E. Arbuzov Institute of Organic and Physical Chemistry, the A. V. Topchiev Institute of Petrochemical Synthesis, the Institute of Heteroorganic Compounds, and the M. M. Shemiakin Institute of Natural Compounds. In the Siberian Division of the Academy of Sciences of the USSR, work in organic chemistry is under way at the Novosibirsk Institute of Organic Chemistry, the Irkutsk Institute of Organic Chemistry, and the Institute of the Chemistry of Petroleum. Research institutes of the Academies of Sciences of the Union republics include the institutes of organic chemistry of the Armenian SSR, the Kirghiz SSR, and the Ukrainian SSR; the A. L. Mndzhoian Institute of Fine Organic Chemistry (Armenian SSR); the Institute of Physical Organic Chemistry (Byelorussian SSR); the P. G. Melikishvili Institute of Physical and Organic Chemistry (Georgian SSR); and the Institute of Organic Synthesis (Latvian SSR).
The National Committee of Soviet Chemists is a member of the International Union of Pure and Applied Chemistry (IUPAC), which organizes biennial congresses, conferences, and symposiums, particularly on organic chemistry.
In the USSR, periodicals that publish works on organic chemistry include Zhurnal organicheskoi khimii (Journal of Organic Chemistry; since 1965), Zhurnal obshchei khimii (Journal of General Chemistry; since 1931), Khimiia geterotsiklicheskikh soedinenii (Chemistry of Heterocyclic Compounds; Riga, since 1965), Khimiia prirodnykh soedinenii (Chemistry of Natural Compounds; Tashkent, since 1965), and Ekspress-informatsiia: Promyshlennyi organicheskii sintez (Bulletin: Industrial Organic Synthesis; since 1960).
Foreign periodicals include Journal of Organic Chemistry (Washington, D.C., since 1936), Journal of the Chemical Society/Perkin Transactions: I. Organic and Bio-organic Chemistry (London, since 1972) and II. Physical Organic Chemistry (London, since 1972), Justus Liebigs Annalen der Chemie (Weinheim, since 1832), Bulletin de la Soaiété chimique de France, part 2 (Paris, since 1858), and Journal of the Society of Organic Synthetic Chemistry of Japan (Tokyo, since 1943).
International journals of organic chemistry include Tetrahedron (New York, since 1957), Tetrahedron Letters (London, since 1959), Synthesis (Stuttgart, since 1969), Synthetic Communications (New York, since 1971), Journal of Organometallic Chemistry (Lausanne, since 1964), Journal of Heterocyclic Chemistry (London, since 1964), Organic Magnetic Resonance (London, 1969), Organic Mass Spectrometry (London, 1968), and Organic Preparations and Procedures International (New York, since 1969). Literature on organic chemistry is abstracted in Chemical Abstracts (Easton, Pa., since 1907), the reference journal Khimiia (Chemistry; since 1953), and Chemisches Zentralblatt (jointly by the German Democratic Republic and the Federal Republic of Germany; Berlin, 1830–1970).
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Butlerov, A. M. Izbr. raboty po organicheskoi khimii. Moscow, 1951.
Markovnikov, V. V. Izbr. trudy. Moscow, 1955.
Hjelt, E. Istoriia organicheskoi khimii s drevneishikh vremen do nastoiashchego vremeni. Kharkov-Kiev, 1937. (Translated from German.)
Schorlemmer, C. Vozniknovenie i razvitie organicheskoi khimii. Moscow, 1937. (Translated from English.)
Giua, M. Istoriia khimii. Moscow, 1966. (Translated from Italian.)
Rodd’s Chemistry of Carbon Compounds, 2nd ed., vols. 1–2. Amsterdam, 1964–68.
Beilsteins Handbuch der organischen Chemie, 4th ed., vols. 1–34. Revised by B. Prager [et al.]. Berlin, 1918–44. (Additional volumes published since 1928.)
Houben-Weyl. Methoden der organischen Chemie, 4th ed., vols. 1–12. Stuttgart, 1953–68.
Kratkaia khimicheskaia entsiklopediia, fascs. 1–5. Moscow, 1961–67.
Nesmeianov, A. N., and N. A. Nesmeianov. Nachala organicheskoi khimii, fascs. 1–2. Moscow, 1969–70.
Neniţescu, C. D. Organicheskaia khimiia, fascs. 1–2. Moscow, 1962–63. (Translated from Rumanian.)
Roberts, J., and M. Caserio. Osnovy organicheskoi khimii, parts 1–2. Moscow, 1968. (Translated from English.)
Fieser, L., and M. Fieser. Organicheskaia khimiia. Moscow, 1966. (Translated from English.)
Chichibabin, A. E. Osnovnye nachala organicheskoi khimii, vols. 1–2. Moscow, 1957–63.
Ingold, C. Teoreticheskie osnovy organicheskoi khimii. Moscow, 1973. (Translated from English.)
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I. L. KNUNIANTS