Head - Cand. Sci. (Chem) Alexey Yu. Vorob'ev

Phone: (383) 330-93-86, internal phone: 3-30
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The laboratory was organized in 1960. Its first head was V.A. Koptyug. Since 1981 V.G. Shubin has been its head.

For all these years the laboratory not only obtained results of world level, but also has been «a smithy of personnels» of a high qualification. Many former employees successfully work in Russia and abroad.

The major scientific trend

• Main direction of the researches: studying of structure and reactivity of cationic complexes of organic compounds.

Scientific achievements

• Mechanism of acid catalyzed isomerization reaction of aromatic compounds has been established by the isotope-labeling method.
• An unique information on electronic and spatial structure of the main types of carbocations,.modeling key intermediates of important reactions of electrophilic substitution, isomerization and condensation of aromatic compounds as well as cationoid rearrangements has been obtained by modern physical methods.
• On the basis of the original methodology based on studying of degenerate processes, structural-kinetics regularities carbocationic rearrangements have been revealedк.
• Foundations of the quantitative theory of molecular rearrangements proceeding with formation of carbocationic intermediates have been laid. Possibility of prediction of the main pathways of multiroute rearrangements of natural terpene compounds has been shown.
• Extensive information on ability of carbocations of various types to chemical transformations that opened new synthetic possibilities in chemistry of aromatic and natural compounds has been obtained.;
• Unexpected acceleration of rearrangement of long-lived carbocation upon transition from solution to a crystal has been found.
• It has been found that reaction of electrophilic fluorination of aromatic compounds is accompanied by isomerization processes;
• It has been established that the DFT method is effective for estimates of rates of degenerate rearrangements of long-lived carbocations.
• A new approach to studying of carbocation cyclization reactions has been formulated and developed. Limited character of the Baldwin rules has been established.
• A new reaction, hydrogen isotope exchange of alkyl groups in arenium ions and their neutral precursors with deuterated acids has been found. On the basis of it a new, simple way to perdeuterated hexamethylbenzene has been developed.
• The dynamic nature of p-complexes of aromatic and related compounds with NO+, RS+ and RSe+ cations has been established. The first study of nitrosonium complex of N-heterocyclic compounds, that of 1,10-phenanthroline has been carried out. A new, bidentate type of linkage of NO+ with N-heterocycle molecule has been found.
• The data testifying to the polar mechanism of fluorination reaction of aromatic compounds with N-fluorobis(phenylsulfonyl)amine have been obtained.
• It has been established that the exception of solvent in process of fluorination of polycyclic aromatic compounds with N-fluorobis(phenylsulfonyl)amine leads to increase of regioselectivity of the reaction.
• New methods of synthesis of basic industrial chemicals (anthraquinone and its derivatives, nitrotoluene, nitromesitylene, etc.), have been developed. These methods provide a high selectivity and improvement of ecological characteristics of the processes.

The major scientific trend of current researchs

• Theory of a chemical structure and chemical bond, kinetics and mechanisms of chemical reactions, reactivity of chemical compounds, stereochemistry, crystal chemistry (RAS).
• Dynamics of elementary chemical transformations, structure and properties of molecules, their assemblies and complexes, substances and materials. Creation and application of new methods of research, including methods of modern quantum chemistry, chemical radiospectroscopy and spin chemistry, laser and photochemistry, including tomographic techniques for chemistry and other applications (SB RAS).

Current projects

• Cationic complexes of N-centered electrophiles with heterocyclic compounds (RFBR).
• Chemical properties and synthetical applications of N-aminated heteroaromatics (RFBR.
• Studying of mechanisms of organic electrophilic reactions (DCMS RAS).
• Mechanisms of electrophilic and nucleophilic organic reactions (SB RAS).

Recent publications (main)

1. В.А. Коптюг. Изомеризация ароматических соединений. (Под ред. Н.Н. Ворожцова мл.). Изд-во СО АН СССР, Новосибирск, 1963. С. 270.
2. Современные проблемы химии карбониевых ионов. Изд-во Наука, Сибирское отделение, Новосибирск, 1975. С. 412.
3. V.G. Shubin. Rearrangements of Carbocatons by 1,2-Shifts, in Contemporary Problems in Carbonium Ion Chemistry I/II. (Ed. Ch. Rees). Springer-Verlag, Berlin, a.o., 1984. P. 267.; On-line
4. V.A. Koptyug. Arenium Ions – Structure and Reactivity, in Contemporary Problems in Carbonium Ion Chemistry III. (Ed. Ch. Rees). Springer-Verlag, Berlin, a.o., 1984. P. 1.
5. Г.И. Бородкин, В.Г. Шубин. Структурно-кинетические аспекты перегруппировок карбокатионов в свете некоторых общих принципов органической химии. В сб. Вопросы физической органической химии. Вып. 2. (Под ред. Б.А. Ершова). Изд-во. ЛГУ, Ленинград, 1984. С. 3.
6. V.G. Shubin and G.I. Borodkin. Some Aspects of Carbocation Rearrangements, in Stable Carbocation Chemistry. (Eds. G.K.S. Prakash and P.v.R. Schleyer). John Wiley & Sons, New York, NY, 1997. P. 231.
7. G.I. Borodkin and V.G. Shubin. Molecular Rearrangements of Cationic Organic Complexes. Chemistry Reviews, Vol. 24, Part 2. Harwood Academic Publ., Amsterdam, 1999. P. 1.
8. В.А. Коптюг. Избранные труды. Т. 1, кн. 1. Изд-во Наука, Москва, 2001. С. 419; Т.1, кн. 2. Изд-во Наука, Москва, 2002. С. 460; Т. 2. Изд-во Наука, Москва, 2003. С.245; Т. 3. Изд-во Наука, Москва, 2006, С.526.