Abstract
Organic electrochemistry (in the Russian scientific literature “electrochemistry of organic compounds”, “EKhOS”) describes the whole field. In addition to electroorganic chemistry (synthesis, organic reactivity, etc), it includes also mechanisms of electrode processes including kinetics of separate stages, electrode and pre-electrode effects, combined spectral and electrochemical techniques, etc., as applied to a variety of objects—from simple molecules to complex natural compounds. The article provides an overview of works in all of these areas performed in the EKhOS's centres of the former USSR: in Moscow, Kazan, Riga, Tula, Novocherkassk, etc. In the second part of the article the author shares over 30-years experience at the Moscow's All-Union Scientific-Research Institute of Vitamins-from the first work with home-made polarograph, studying the mechanisms of reactions, to large-scale industrial electrosynthesis. Along with biographical material, author describes also the environment in which soviet scientists lived and worked in those years.
An erratum of the original chapter can be found under DOI 10.1007/978-3-319-21221-0_17
An erratum to this chapter can be found at http://dx.doi.org/10.1007/978-3-319-21221-0_17
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Notes
- 1.
He performed the thesis “Study of polarizability of complex molecules” under the supervision of Yakov Kivovich Syrkin, a member of the USSR Academy of Sciences, one of the leading Soviet theoretical chemists. In 1951, Syrkin was accused of “cosmopolitanism and propaganda of ideologically misguided resonance theory” and, together with Frumkin , of underestimation of the “decisive contribution of Russian scientists to physical chemistry” (due to their joint article in the Great Soviet Encyclopedia). This was followed by dismissal of Syrkin from the Karpov Institute of Physical Chemistry and by dismissal of Frumkin as director of the Institute of Physical Chemistry of the USSR Academy of Sciences.
- 2.
Here and below we use the system of abbreviated notation of electrode reactions (see Appendix). Thus, a complete schema of reactions (9.2) is written as “–e(d)(h)a–e–p,” where “–e,” “h,” and “–p” are transfers of electron, hydrogen, and proton, “d” and “a” are C–N bond dissociation and C–C bond association, and in the brackets (d)(h) are parallel stages.
- 3.
M.E. Vol’pin (1923–1996) was a Dr. chem. sci. (1959), an academician (1987), and the director of INEOS (1988–1996). Vol’pin got a contract at INEOS only as a result of persistent efforts of Kursanov in 1958, 3 years after he began work unofficially for free in Kursanov ’s laboratory, because of restrictions for persons of Jewish nationality (see [54]). I met them both during my unsuccessful application to INEOS in 1961 (see Sect. 9.2).
- 4.
- 5.
The “Knunyants ’s lactone” for acetobutyrolactone and “Knunyants ’s regrouping” are established terms in the literature.
- 6.
This “closed” organization was also called NII-42: a number is assigned to each “closed” organization and in everyday use they were called “numbered enterprises,” “mailboxes,” or simply “boxes.”
- 7.
Biographical material is taken from [95].
- 8.
Biographical data for this section were mainly taken from the book [98].
- 9.
Recall that the phenomenon itself and the method of ESR were discovered by Ye.K. Zavoysky in Kazan, KGU, in 1944.
- 10.
According to the memoirs of A.P. Tomilov , Yu.M. Kargin proposed to use an acronym EKhOS in the title of national conferences [89].
- 11.
Yan Pavlovich Stradyn in Russian transcription.
- 12.
Ya.P. Stradyn and R.A. Gavar presented this material on the CITCE’s 14th meeting, Moscow, 19–25 August 1963 (as per Dr. V. Glezer). Their work [125, 126] on in situ EC-ESR of nitrofurans has been published about a year before that of the Kazan scientists [105]. Geske and Maki [127] are commonly considered the pioneers of the in situ EC-ESR. However, Alexander Galkin and coworkers in the Kharkov FT I (Kharkov Physics-Technical Institute) in 1957 [128] were the first to carry out in situ electrochemical generation in the ampule of an ESR spectrometer.
- 13.
In a small room, in front of the cathedral library, we had worked together with Andrey Mirzabekov (1937–2003)—the future academician and director of V.A. Engel’gardt Institute of Molecular Biology USSR AS and future director of Biochip Technology Center at Argonne National Laboratory, USA. I worked on polarograph and Andrej on preparative chromatograph. The room was not equipped with ventilation and Nikolai Alekseevich asked us daily if there was any toxic contamination by mercury or solvent. Understanding our responsibility, Andrey and I worked neatly and carefully.
- 14.
I had a bad experience with another academic institution, INEOS. In 1961, prior to the work assignment to VNIVI, on the recommendation from my brother, Stal’ Mairanovskii, I was invited for an interview by Dr. Zinaida Naumovna Parnes; she studied hydride transfer reactions. She gave me reprints of her articles and asked me to think about the application of electrochemistry. A few days later, in INEOS, I met Dr. Parnes and Dr. Mark Yefimovitch Vol’pin again to continue our discussion. They were satisfied with my interview and suggested I apply for employment to the Director, acad. A.N. Nesmeyanov and introduced me to D.N. Kursanov , corr. member of USSR AS, the head of their department. Kursanov signed my letter and wished me a bright future in INEOS. Just a week later, I had a call from Dr. Z. Parnes, and she asked me to come: INEOS’s “pervyy otdel” blocked my admission (about the pervyy otdel, or first department, see Sect. 9.2.8).
- 15.
- 16.
The electrochemistry of carotenes and porphyrins was the topic of the Ph.D. theses of Askold Anatoliyevich Engovatov (carotenes) (1975) and Ichtior Muradovich Muratov (porphyrins) (1986).
- 17.
We consider it advisable to divide reactions into three groups: (1) with slow and moderately fast cleavage 0 < k *d < 103 s–1 (SMFR) and (2) fast 103 < k *d < 1010 s–1 (FR) and (3) ultrafast cleavage (UFR) k *d ≥ 1010 s–1 [225].
- 18.
- 19.
Publications in Doklady AN SSSR had to be submitted by a member of the Academy of Sciences (academician).
- 20.
The term “redox catalysis” [258] that is often used instead of HOMEC in the literature is inadequate, because it does not reflect the involvement of the electrode itself in the electrochemical reaction (stage “e”) and the homogeneous character of the ЕТ on the substrate (stage “e v ”). In additions, this term is widely applied to other phenomena. The involvement of the electrode is also not expressed by the term “homo-mediator system” [259]. Starting from Kobozev and Monblanova [260], the term “electrocatalysis” became accepted for heterogeneous electrode reactions, and the “homogeneous electrocatalysis,” HOMEC, involves both e and e v stages.
- 21.
These studies are included in the Ph.D. thesis of Leonid Yu. Yusefovich (1978).
- 22.
This hypothesis is supported by the first results of viscosity measurements in the pre-electrode layer at a distance of δ < 6 nm [274] using an idea of combined EC-AFM method [275]. After the symposium [275], Prof. Dieter Kolb introduced me to a group of scientists from Mainz, they invited me to hold a seminar and we had a joint project. Prof. Kolb followed it with great interest. I fondly and with gratitude remember this outstanding electrochemist (1942–2011).
- 23.
This work became the basis of Ph.D. dissertation by Nina Fyodorovna Loginova (1977).
- 24.
The materials given in this section were the object of a large number of “closed” USSR author’s certificates; they entered in the closed (not openly accessible) Ph.D. dissertations by Inna Alekseyevna Titova (1979) and Isaac Grigorjevich Gitlin (1985).
- 25.
The pervyy otdel (first department) in the Soviet organizations oversaw the hiring of staff, travel abroad, access to information, foreign correspondence and publications, and use of typewriters and copiers (countering the “samizdat,” i.e., reprint of banned literature). The information about employees, their political views, etc., was also filed there.
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Acknowledgments
I am grateful to my wife, Dr. Bella Lurik , for her support during the writing of this work, for advice, and for memories of some events and meetings.
I express my gratitude, to Drs. Galina Bekker, Victor Glezer, Naftolij Ioffe, Vladimir Kurmaz, Emma Malakhova, Feliks Mairanovsky, Irena Mayranovsky, Elena Obol’nikova, Vladimir Petrosyan, Garislav Shkolenok, Igor’ Sirotin, Mikhail Yanotovskiy , and El’sa Zacharova for providing valuable materials and photos; and to Yulia Polyak for her work with photos.
I sincerely thank Dr. Boris Kahn and Dr. Stephan Samvelyan for their assistance with translation and especially my daughter Dr. Elena Boyd for her advice, changes, and corrections.
My special thanks to Dr. Fritz Scholz for his comprehensive help with this article and the whole idea—to write a book about the work of scientists under conditions of a unique historical experiment, which divided mankind in two worlds.
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Appendix: Symbolization of Electrode Reactions (Based on [299])
Appendix: Symbolization of Electrode Reactions (Based on [299])
Symbols “e,” “e v ,” and “ε” refer, correspondingly, to the heterogeneous, “volume” (without of any electrode interface effects) and solvated electron transfer; “c” and “c s ” refer to the volume and “surface” chemical stages. Designation of chemical stages “c”: according to particle, “p” (proton) and “h” (hydrogen), “minus” for detachment of a particle, and for attachment of a particle the “+” sign is omitted; and according to the type of reaction, “a” (association, bond formation), “d” (dissociation, bond cleavage), and “r” (rearrangement, isomerization). The subscripts N, E, R, and M (nucleophil, electrophil, radical reagents, material of the electrode) are used to indicate the nature of the substances; the subscript “2” is used for the dimerization reaction. The parallel reactions, the reactions of the second substance, and the “concert reactions” are written in the brackets ( ), [ ], and { }, correspondingly. The origin and the carry points of reagents may be indicated by the arrows “↑” and “↓,” correspondingly. Capital А and С letters may precede the reaction schema in order to distinguish between anodic and cathodic processes. The overall number of stages and the transported particles are given with the “∑” sign, for example, ∑2edp [cf. Reaction (9.7a)]. When written compactly, the symbols are entered directly in the reaction equation [cf. Reaction (9.6)].
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Mairanovsky, V.G. (2015). Organic Electrochemistry in the USSR. In: Scholz, F. (eds) Electrochemistry in a Divided World. Springer, Cham. https://doi.org/10.1007/978-3-319-21221-0_9
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