Б’янка Чубар – революціонерка французької органічної хімії

Virtually unknown in her homeland, Bianka Tchoubar, born in 1910 in Kharkiv, brought about a true paradigm shift in French organic chemistry of the 20th century. Originality of research ideas, scientific rigor and legendary perseverance earned her respect and recognition in the world scientific comm...

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Опубліковано в:Журнал органічної та фармацевтичної хімії
Дата:2022
Том:20
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Сторінки:6-13
ISSN:2518-1548
Автори та афіліації:
  • Romana-Iryna Yu. Martyniak — École Normale Supérieure, Paris Sciences et Lettres University
Автор: Martyniak, Romana-Iryna Yu.
Формат: Стаття
Мова:Англійська
Опубліковано: National University of Pharmacy 2022
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description Virtually unknown in her homeland, Bianka Tchoubar, born in 1910 in Kharkiv, brought about a true paradigm shift in French organic chemistry of the 20th century. Originality of research ideas, scientific rigor and legendary perseverance earned her respect and recognition in the world scientific community. This eccentric Parisian of Ukrainian origin became the first woman to enter the French National Center for Scientific Research (Centre National de la Recherche Scientifique, CNRS) upon its creation in 1939. Bianka Tchoubar’s contribution to the study of reaction mechanisms and salt effects in organic chemistry were of paramount importance, and so were her efforts to present these novel scientific concepts to the audience of French organic chemists through the clear and concise expression of her books. The name of this great Ukrainian researcher may be found in the pages of French organic chemistry textbooks, where the Demjanov ring expansion reaction is called the Demjanov–Tiffeneau–Tchoubar rearrangement. This article aims at presenting the outstanding scientific legacy and turbulent life path of this researcher to the world scientific community.
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fulltext ISSN 2308-8303 (Print) / 2518-1548 (Online) 6 Life Devoted to Science http://ophcj.nuph.edu.ua UDC 547.2 929 R.-I. Yu. Martyniak Department of Chemistry, École Normale Supérieure, Paris Sciences et Lettres University, 24, rue Lhomond, Paris, 75005, France Bianka Tchoubar: A Revolutionary in French Organic Chemistry Abstract Virtually unknown in her homeland, Bianka Tchoubar, born in 1910 in Kharkiv, brought about a true paradigm shift in French organic chemistry of the 20th century. Originality of research ideas, scientific rigor and legendary perseverance earned her respect and recognition in the world scientific community. This eccentric Parisian of Ukrainian origin became the first woman to enter the French National Center for Scientific Research (Centre National de la Recherche Scientifique, CNRS) upon its creation in 1939. Bianka Tchoubar’s contribution to the study of reaction mechanisms and salt effects in organic chemistry were of paramount importance, and so were her efforts to present these novel scientific concepts to the audience of French organic chemists through the clear and concise expression of her books. The name of this great Ukrainian researcher may be found in the pages of French organic chemistry textbooks, where the Demjanov ring expansion reaction is called the Demjanov–Tiffeneau–Tchoubar rearrangement. This article aims at presenting the outstanding scientific legacy and turbu- lent life path of this researcher to the world scientific community. Keywords: mechanisms of organic reactions; charged intermediates; salt effects; molecular rearrangements; alicyclic compounds; history of chemistry Р.-І. Ю. Мартиняк Хімічний факультет, Вища нормальна школа, Паризький дослідницький університет, вул. Ломон, 24, м. Париж, 75005, Франція Б’янка Чубар – революціонерка французької органічної хімії Анотація Маловідома на Батьківщині уродженка Харкова Б’янка Чубар зуміла створити справжню зміну парадигми у фран- цузькій органічній хімії XX століття. Оригінальністю наукових ідей, експериментальною майстерністю та непохитністю власних переконань ця науковиця здобула неабияке визнання у Франції та цілому світі. Ексцентрична парижанка українського походження стала першою жінкою, що увійшла до дослідницького штату Національного центру науко- вих досліджень Франції (Centre National de la Recherche Scientifique, CNRS) під час його створення 1939 року. Внесок науковиці у механістичні дослідження органічних реакцій, а також їх педагогічне опрацювання є неоціненними. Прізвище великої українки гордо майорить у французьких підручниках органічної хімії, які вшановують її експеримен- тальні дослідження, називаючи реакцію розширення аліциклів, відому як перегрупування Дем’янова, перегрупуван- ням Дем’янова–Тіффано–Чубар. Пропонована стаття має на меті репрезентувати науковій спільноті України та світу видатні здобутки й непростий життєвий шлях цієї дослідниці. Ключові слова: механізми органічних реакцій; заряджені інтермедіати; сольові ефекти; молекулярні перегрупування; аліциклічні сполуки; історія хімії Citation: Martyniak, R.-I. Yu. Bianka Tchoubar: A revolutionary in French organic chemistry. Journal of Organic and Pharmaceutical Chemistry 2022, 20 (2), 6 – 13. https://doi.org/10.24959/ophcj.22.255945 Received: 02 May 2022; Revised: 10 June 2022; Accepted: 12 June 2022 Copyright© 2022, R.-I. Yu. Martyniak. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0). Funding: the author received no specific funding for this work. Conflict of interests: the author has no conflict of interests to declare. ISSN 2308-8303 (Print) / 2518-1548 (Online) 7 Journal of Organic and Pharmaceutical Chemistry 2022, 20 (2) ■ Biography 1. Early Life and Education Bianka Tchoubar was born on the 22nd of October, 1910, in the Ukrainian city of Kharkiv, which was then part of the Russian Empire. The Tchoubar family belonged to the Jewish sect of the Karaites [2]. Bianka’s father, Ilya Tchoubar, was a Kharkiv lawyer with Menshevik views. He was a mem- ber of the Liberal Party of Constitutional Demo- crats (Cadets) and a person close to its leaders, Pavel Milyukov and Vladimir Nabokov. To avoid political repression after the advent of Bolshevik power in Russia and the occupation of the Ukrainian People’s Republic, the Tchoubar fami- ly (a couple with two children, Bianka and her brother Serhiy) were forced to leave Ukraine in 1920. The family settled in Constantinople, then the capital of the still-existing Ottoman Empire. Due to political instability caused by World War I, the collapse of the Ottoman Empire and the Turkish War of Independence, the Tchoubar family only lived in Constatinopole for a short time and moved to Budapest in 1922, where the brother of Ilya Tchoubar lived. The parents then moved to Paris, and the girl and her brother stayed with their uncle, where they were able to study French. The family reunited in Paris in 1924 [3]. After settling in Paris, Bianka Tchoubar converted to Orthodox Christianity in 1925, but soon became disappointed in religion and began to adhere to an agnostic worldview [2]. Bianka’s father died of a heart attack in the early 1930s, leaving his wife and two children with little livelihood. To survive, Bianka’s mother worked at minimal-wage and non-permanent jobs, selling perfumes during the day and being a cloak- room attendant at a theater in Paris in the eve- nings. The family lived in extreme poverty [3]. Bianka Tchoubar and her brother began their studies at a Russian school in the 16th arron- dissement of Paris, set up by the French govern- ment for the children of political migrants from the Russian Empire. It was at this school that Bianka Tchoubar first became interested in the natural sciences, including chemistry, under the tutelage of Mademoiselle Chamier, a Russian che- mist who had collaborated extensively with Marie and Pierre Curie in the past. Bianka Tchoubar later reminisced about this teacher as her mother in chemistry [3]. The figure of Marie Curie was extremely important to Bianka Tchoubar; she has repeatedly stated that she had never missed any of Curie’s public lectures in Paris [1]. Bianka Tchoubar continued her studies in chemistry, getting admitted to the Sorbonne University in 1929. In 1931, she received the Bachelor of Science Degree and began her re- search work under the guidance of the then- famous Parisian chemist Professor Paul Freundler, a close friend and colleague of Joseph Achille Le Bel. The choice of the laboratory for her graduate research activities was due to Bianka Tchoubar’s interest in asymmetric ni- trogen reactions. Figure 1. Bianka Tchoubar with a cigarette. The portrait is reproduced from reference [1] ISSN 2308-8303 (Print) / 2518-1548 (Online) 8 Журнал органічної та фармацевтичної хімії 2022, 20 (2) In Professor Freundler’s group, the young scientist first met with the rejection of her ideas about organic ions by her French colleagues. The conflict of scientific worldviews stemmed from the considerable conservatism of the French sci- entific community to any new concepts, especially if they came from the so-called “Anglo-Saxon world” [1]. Despite the disagreement of her su- pervisor, Bianka Tchoubar devoted her Master thesis to the study of charged organic species in tertiary amine reactions with ethyl iodoacetate, which contributed to her Higher Education Degree in Chemistry, awarded in 1932 (Diplôme d’Études Supérieures de Sciences Chimiques) [3]. 2. Scientific Work with Marc Tiffeneau In 1933, Bianka Tchoubar began working in the laboratories of the Faculty of Medicine of the University of Paris, under Marc Tiffeneau’s super- vision. Despite world recognition of his achieve- ments, Marc Tiffeneau had limited recourse to resources in France and was forced to work in the field of pharmaceutical chemistry. He became Bianka Tchoubar’s most important mentor. Bianka’s first research article on the interaction of Grignard reagents with chlorocyclohexanones was published in 1934 in Proceedings of the French Academy of Sciences (Comptes rendus de l’Académie des Sciences) [4]. In the laboratory of Marc Tiffe- neau, Bianka Tchoubar first met Jeanne Lévy, an organic chemist, who later became one of her research collaborators [3]. In 1937, Bianka Tchoubar established the Laboratory of Organic Chemistry, which studied a variety of atomic transfer reactions. She was ap- pointed also as a trainee researcher at the newly established French National Center for Scientific Research (Centre national de la recherche scientifi- que – CNRS), becoming the first female researcher to enter this institution for science (Figure 1) [2]. She then became interested in molecular rearran- gement reactions and proposed a mechanism for nitrite deamination of alicyclic primary amines with ring expansion (Scheme 1) using quantum mechanical theories of chemical bonding. These were considered to be the so-called “English ideas” in France at the time, and viewed as un- welcome. Despite numerous disagreements and criticism of peers, the joint research of Bianka Tchoubar and Marc Tiffeneau made it possible to definitively establish the mechanism of the Tiffeneau–Demjanov rearrangement (or, as it is known in France, the Demjanov–Tiffeneau– Tchoubar rearrangement) (Scheme 2) [5, 6]. OH NH2 HNO2 O Scheme 1. Demjanov–Tiffeneau–Tchoubar rearrangement HO N O OH2H O N O H H O N O H H H H H 2 3 2 2 O O O O O N O N O - - - H2O OHNH H O N O N O OHNN H O OHNN HO OH2H - 2 -HNO OHNN O H H OH N N -H2 2O H3O- - O H H2O O N Scheme 2. Demjanov–Tiffeneau–Tchoubar rearrangement mechanism ISSN 2308-8303 (Print) / 2518-1548 (Online) 9 Journal of Organic and Pharmaceutical Chemistry 2022, 20 (2) Bianka Tchoubar’s research slowed down significantly in 1939–1945 due to the outbreak of World War II, when she took an active part in the French national resistance to the fascist occupation [2]. The sudden death of Marc Tiffeneau in 1945 further complicated Bianka Tchoubar’s scientific career. However, after the war in 1945, Bianka’s longtime friend Jeanne Lévy, an Associate Pro- fessor of Medicine at the University of Paris at that time, was appointed to establish a new Institute of Medicine in Paris, known today as the Fournier Institute (Institut Fournier) [2, 3]. Bianka Tchoubar joined the research department of the newly established Institute, and in 1946 published her thesis “Contribution to the study of alicyclic expansion mechanisms: nitrite deami- nation of 1-aminomethylcyclohexanols” [2]. Bianka Tchoubar managed to present these radically new ideas in physical organic chemistry while obtaining her doctorate. The significant delay in defending her doc- toral thesis was caused by the political instabili- ty in France of 1930s, as well as by the outbreak of World War II. The completion of her PhD was also delayed by the unwillingness of the French scientific community to accept the innovative but “English” concepts Bianka Tchoubar promoted. The young researcher explicitly stated her interest in charged intermediates of organic reactions. Her ambition was to rule the notions of “affinity capacity” and “migratory aptitude” out of organic chemistry as they did not provide satisfactory ex- planations for the observed patterns in alicyclic expansion reactions. Such ideas of Bianka Tchoubar were severely criticized in Parisian scientific circles of that time [2]. During the defense of the Bianka Tchoubar’s thesis, the opponent, French spectro- scopist Pauline Ramar-Luca, called the presented explanations of the reaction mechanisms “ephe- meral theories”. The only supporter of the young scientist’s novelties was the chairman of the doc- toral jury, Edmond Bauer. The theoretical chemist was impressed by the Bianka’s work and accepted her ideas with enthusiasm and encouragement. The Bianka Tchoubar’s doctoral thesis was the first French research work to explain organic reaction mechanisms in terms of mesomerism and the formation of charged intermediates. Bianka Tchoubar was responsible for bringing the widely accepted ideas of Hans Meerwein, who postulated the existence of carbocationic intermediates in the pinacol–pinacolone rearrangement between 1922 and 1927, to French organic chemistry [2]. 3. “Anglo-American” Theories and Center No.12 of the French National Center for Scientific Research French colleagues never refrained from criti- cism for Bianka Tchoubar’s pertinent and witty interpretations of the mechanistic features of chemical reactions “with English accent”. Rejec- tion and occasional ridicule of her ideas did not cease even after she was awarded her doctorate degree. It should be noted that French organic chemistry in the twentieth century had a rather strong “chauvinistic inclination” [7]. Achievements of quantum mechanics introduced into chemistry by the American and British chemists led by Linus Pauling and Christopher Ingold were rejected. That the 1912 Nobel Prize in Chemistry that was jointly awarded to two French researchers, Victor Grignard and Paul Sabatier seemed to have an im- pact to this field of science in France. This gesture of recognition of the French chemical science led to its isolation and Franco-centricity for the decades to come. There was an excessive and sometimes biased emphasis on selected research only because of their performance in France, a politicized ap- proach to research funding and staffing, and de- liberate prevention of scientific progress through the introduction of external scientific ideas from the so-called “unfriendly” countries. Moreover, the extremely influential Parisian chemists Charles Prévost and Albert Kirrmann monopolized French organic chemistry in the post-war period. They had been promoting Prévost’s theory of organic re- actions from their position of power, despite its ridicule at the international level. Prévost’s ac- counts of organic reactions formulated in terms of “syniony” and “metiony”, despite their outright inconsistency, had thus become the only acceptable theory in French laboratories and classrooms after World War II. In addition to the anti-British and anti-American sentiments that prevailed in the French society after World War II, as a result of the Vichy regime’s propaganda, the French govern- ment had also established control over the cir- culation of English literature, manifested in its artificially limited availability [7]. The French reluctance to accept the revolu- tionary ideas of their British and American counterparts was the main reason of the Bianka Tchoubar’s scientific career slowdown at the French National Center for Scientific Research. Due to the inconsistency of political views, her appointment to a full-time research position was delayed until 1955. In 1957 – 1958, Bianka Tchoubar organized countless seminars, at which ISSN 2308-8303 (Print) / 2518-1548 (Online) 10 Журнал органічної та фармацевтичної хімії 2022, 20 (2) she presented the electronic theories of organic reactions [1 – 3, 7]. As a summary of seminar re- ports, in 1960, she wrote a book “Mechanisms of Organic Reactions”, which was the first French textbook to present the quantum theories of che- mical bonding. The famous quotation of Claude Bernard was chosen as the epigraph for this book: “If a theory was considered perfect and was no longer tested, it would have become a dogma” [8, 9]. The book was positively accepted by the world scientific community and translated into six lan- guages [1 – 3, 7]. The presentation of the already widely accepted quantum-mechanical theories of chemical bonding to the French audience has led to a paradigm shift in the 20th century French organic chemistry [7]. As early as in 1961, Bianka Tchoubar was ap- pointed Director of Research at the French Na- tional Center for Scientific Research and headed her first research group at the Institute for Che- mistry of Natural Substances in Gif-sur-Yvette, Île-de-France. Bianka Tchoubar’s ideas were re- cognized even more widely in 1968, when she was appointed Director of Research at Center no.12 of the French National Center for Scientific Re- search in Thiais, Île-de-France. This research group included more than 70 chemists who conducted extensive research in various fields of organic chemistry. It was the largest center for organic chemistry research in France at that time [2]. Scientific research at Center no.12 has focused on the fundamental study of organic reaction mechanisms. Considerable attention was also paid to the synthesis of biologically active substances and drug development. Under the supervision of Bianka Tchoubar at the CNRS Center no.12, the antispasmodic drug Spasmodex was developed. The active compound of this drug is dihexyverine (2-(piperidin-1-yl)-ethyl-[1,1’-bi(cyclohexane)]- 1-carboxylate) (Figure 2) [3]. Colleagues and students reminisce about Bianka Tchoubar being a gifted research supervisor, whose priority was a friendly atmosphere in the group. Bianka Tchoubar took each and every aspect of the research papers published under the CNRS Center no.12 affiliation as her personal responsi- bility. For these reasons, no research work in these laboratories was published without prior review by Bianka, even as she did not claim co-authorship in these works, thereby paving the path for young scientists. That is why, in 10 years of managing the laboratories of Center no.12, she agreed to put her name in 5 publications only, instead giving the real distinction to her colleagues [2, 3]. Monday seminars of young researchers were another tradition at Center no.12, led by Bianka Tchoubar. Former graduate students of Bianka recall that she appeared to be always shrouded in a thick cloud of cigarette smoke at the seminars. Her presence in the front rows of the auditorium was ubiquitous, where she actively and passionately discussed research results. Not self-serving, this scientist never used her established authority to dominate scientific discussions, which earned her the respect of colleagues [1 – 3]. Bianka Tchoubar tirelessly incorporated the ideas of quantum chemistry into the interpreta- tion of the results obtained in her own laborato- ries. Despite the experimental nature of her own research, she was also interested in the achieve- ments of theoretical branches of chemistry, which were developing extremely rapidly in that pe- riod [2]. 4. Scientific Research in the USSR and Last Years of Life Bianka Tchoubar first met with Yevhen Shilov at the IUPAC International Congress of Applied Chemistry in Paris in 1957. Dr. Shilov was the Head of the Laboratory of Organic Reaction Me- chanisms of the Institute of Organic Chemistry of the Ukrainian Soviet Socialist Republic Acade- my of Sciences (Figure 3). Having common in- terests and like-minded scientific views, a deep friendship grew between Bianka Tchoubar and Yevhen Shilov. Likewise, these same common- alities led to the subsequent friendship with his son, Oleksandr Shilov, who later became an aca- demician of the USSR and of the Soviet Academy of Sciences [10]. The friendship with the Shilovs was the impetus for Bianka Tchoubar’s research in the field of coordination chemistry. In 1974, Bianka Tchoubar began studying the reduction of molecular nitrogen in coordination compounds of iron. She conducted such research in collaboration with colleagues and friends from the former Soviet Union, including Yevhen Shilov from the Academy of Sciences of Ukraine, with whom she met several times at the Institute O O N Dihexyverine (Spasmodex) Figure 2. Dihexyverine structure ISSN 2308-8303 (Print) / 2518-1548 (Online) 11 Journal of Organic and Pharmaceutical Chemistry 2022, 20 (2) of Organic Chemistry of the National Academy of Sciences of Ukraine in Kyiv. Much of the research in this period of her life was conducted with the lead- ing Soviet organic chemists Alla and Oleksandr Shilov (Figure 4), as well as with the 1956 Nobel Laureate in Chemistry Nikolai Semenov [1 – 3]. The results of iron complexes investigation led to amassing of a significant array of data on the salt effect influence on organic reaction kinetics [2, 11]. During her last years at the French National Center for Scientific Research, Bianka Tchoubar actively collaborated with the French spectrosco- pists Didier Astruc and Georges Bram. Their joint research was dedicated to the study of microwave activation effects on organic reactions, as well as to the organic reactions occurring in the ab- sence of the solvent [3]. Bianka Tchoubar officially retired from the French National Center for Scientific Research in 1978, but never left her love of science behind, continuing to be active in new for her fields of organic chemistry. In 1981, Bianka Tchoubar was awarded the Louis Jecker Prize (Prix Jecker) of the French Academy of Sciences. Interestingly, Bianka’s mentor, Marc Tiffeneau, received this award three times: in 1911, 1922 and 1923 [3]. Together with André Loupy in 1988, she wrote a book “Salt Effects in Organic and Organo- metallic Chemistry”, which was translated into several foreign languages [2, 11]. The last experiments Bianka Tchoubar con- ducted were designed to study solvent effects on the competition of SN2 and E2 reactions [2]. Her last paper was a literature review “Salt Effects as a Result of Ion Vapor Exchange” published in the Chemical Review, co-authored with André Loupy and Didier Astruc [12]. In total, Bianka Tchou- bar authored some 140 scientific papers [3]. Bianka Tchoubar passed away on April 24, 1990, and was buried at the Sainte-Geneviève- des-Bois cemetery in the Essonne department, Île-de-France. ■ Books Mechanisms of organic reactions (1960) This textbook easily fitting in a lab coat pocket was a huge success and quickly earned the nickname of “The Little Tchoubar”. Figure 3. Bianka Tchoubar with the Head of the Laboratory of Organic Reaction Mechanisms of the Institute of Organic Chemistry of the Ukrainian Soviet Socialist Republic Academy of Sciences Dr. Yevhen Shilov in Paris (1957). The picture is reproduced from reference [10] ISSN 2308-8303 (Print) / 2518-1548 (Online) 12 Журнал органічної та фармацевтичної хімії 2022, 20 (2) The first four chapters of the book are dedi- cated to molecular orbital hybridization, bond polarity and polarizability, inductive and meso- meric electronic effects, and modern theories of acids and bases. These sections reflected the in- fluence of Christopher Ingold’s research in the field of organic chemistry [9]. The remaining nine chapters cover some is- sues of chemical kinetics and transition states, as well as individual aliphatic substitution re- actions, elimination and addition reactions, as well as prototropic processes, carbonyl group re- actions, and aromatic substitutions [9]. There were several mechanistic interpreta- tions that turned out to be proven wrong with time. In particular, the textbook proposes a carbanion mechanism of deuteroexchange with halogenated substrates, instead of E2. However, the overall content of the textbook has withstood the test of time, with such inaccuracies being rare occur- rences [13]. Salt effects in organic and organometallic chemistry (1988) This book was co-authored with André Loupy. The first chapters of the book discuss the ba- sics of the theory of Lewis acids and bases, ion pairs, salt effects in chemical bond cleavage, electrophilic and nucleophilic induction of hete- rolytic bond cleavage in halogenated substrates, specific salt effects in SN2 reactions, salt effects during multiple bonding reactions in ketones, esters, and nitriles, drying effects, bifunctional catalysis and electrophilic addition to carbon- carbon double bonds. Subsequent sections examine salt control over regioselectivity, stereoselectivity of substitution, addition, and elimination reactions, as well as the means of controlling the chemical equilibrium by salt and solvent effects. The final section of the book analyzes the role of the aforementioned phenomena in organo- metallic chemistry [11, 14]. ■ Acknowledgments The author expresses her gratitude to Roald Hoffmann, 1981 Nobel Laureate in Chemistry, Emeritus Professor at Cornell University, and a dear friend of Bianka Tchoubar’s, for relating his unique memories about Tchoubar’s life and work. Additional thanks go to Professor Mykola Obushak, Head of the Organic Chemistry Department at Ivan Franko National University of Lviv, for supporting the author in the writing of this article. Figure 4. Bianka Tchoubar with the Shilovs. Left to right: Alla Shilova, Bianka Tchoubar, and Oleksandr Shilov. The figure is reproduced from reference [2] ISSN 2308-8303 (Print) / 2518-1548 (Online) 13 Journal of Organic and Pharmaceutical Chemistry 2022, 20 (2) ■ References 1. Astruc, D. Bianka Tchoubar (1910 – 1990). In European Women in Chemistry; Apotheker, J., Sarkadi, L. S., Eds.; Wiley–VCH Verlag GmbH: 2011; pp 17 – 20. 2. Jacquesy, R. A.; Loupy, A.; Gruselle, M. Bianka Tchoubar, La Révolution des Mécanismes. Actual. Chim., 2015, 397 – 398, 8 – 10. 3. Jacques, J. Bianka Tchoubar (1910 – 1990). New J. Chem. 1992, 16, 11 – 14. 4. Tiffeneau, M.; Tchoubar, B. Mécanisme de la Formation des Alcoyl–Cyclohexanones par Actions des Dérivés Organomagnésiens sur les α-Chlorocyclohexanones. Remplacement Non-Direct de L’Halogène par L’Alcoyle. C. R. Acad. Sci. Paris. 1934, 198, 941. 5. Olson, J. O.; Shea, K. M. Critical Perspective: Named Reactions Discovered and Developed by Women. Acc. Chem. Res. 2011, 44 (5), 311 – 321. https://doi.org/10.1021/ar100114m. 6. Rulev, A. Yu.; Voronkov, M. G. Women in Chemistry: A Life Devoted to Science. New J. Chem. 2013, 37 (12), 3826 – 3832. https://doi.org/10.1039/C3NJ00718A. 7. Laszlo, P. How an Anglo-American Methodology Took Root in France. Bull. Hist. Chem. 2011, 36 (2), 75 – 81. 8. Rulev, A. Yu. Zhenskie Dat’ Imena [Let Us Give Them Feminine Names, in Russian]. Himiya i Zhizn’ 2019, 3, 28 – 31. 9. Tchoubar, B. Les Mécanismes Réactionels en Chimie Organique; Dunod, 1960. 10. Shilov Ye. A.: Biobibliograficheskiy Ukazatel’ [Shilov Ye. A.: A Biobibliographical Guide, in Russian]; Ganushkina, V. V., Talanova, M. N., Koyfman, O. I., Eds.; Information Сenter of The Ivanovo State University of Chemistry and Technology (ChemTech Golden Series), 2010. 11. Loupy, A.; Tchoubar, B. Effets de Sels en Chimie Organique et Organométallique; Dunod, 1988. 12. Loupy, A.; Tchoubar, B.; Astruc, D. Salt Effects Resulting from Exchange between Two Ion Pairs and Their Crucial Role in Reaction. Chem. Rev. 1992, 92 (6), 1141 – 1165. https://doi.org/10.1021/cr00014a001. 13. Kende, A. S. Les Mécanismes Réactionnels en Chimie Organique. J. Am. Chem. Soc. 1965, 87 (7), 1632-1632. https://doi.org/10.1021/ja01085a055. 14. Normant, J. F. Effets de Sels en Chimie Organique et Organométallique: by A. Loupy and B. Tchoubar, Ed. Dunod, Paris 1988, p. 311, ISBN 2-04-16986-5, ff. 350. J. Organomet. Chem. 1989, 362 (3), C33. https://doi.org/10.1016/0022-328X(89)87265-1. Information about the author: Romana-Iryna Yu. Martyniak, Master Student at the Department of Chemistry, École Normale Supérieure, Paris Sciences et Lettres University; Intern at the Laboratory of Molecular Simulation, Institute of Chemical Sciences and Engineering, School of Basic Sciences, École Polytechnique Fédérale de Lausanne; https://orcid.org/0000-0003-2419-7090; e-mail for correspondence: romana-iryna.martyniak@ens.psl.eu; tel. +41 76 4136139.
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spelling oai:ojs.journals.uran.ua:article-2559452026-08-24T13:21:16Z Bianka Tchoubar: A Revolutionary in French Organic Chemistry Б’янка Чубар – революціонерка французької органічної хімії Martyniak, Romana-Iryna Yu. mechanisms of organic reactions charged intermediates salt effects molecular rearrangements alicyclic compounds history of chemistry механізми органічних реакцій заряджені інтермедіати сольові ефекти молекулярні перегрупування аліциклічні сполуки історія хімії Virtually unknown in her homeland, Bianka Tchoubar, born in 1910 in Kharkiv, brought about a true paradigm shift in French organic chemistry of the 20th century. Originality of research ideas, scientific rigor and legendary perseverance earned her respect and recognition in the world scientific community. This eccentric Parisian of Ukrainian origin became the first woman to enter the French National Center for Scientific Research (Centre National de la Recherche Scientifique, CNRS) upon its creation in 1939. Bianka Tchoubar’s contribution to the study of reaction mechanisms and salt effects in organic chemistry were of paramount importance, and so were her efforts to present these novel scientific concepts to the audience of French organic chemists through the clear and concise expression of her books. The name of this great Ukrainian researcher may be found in the pages of French organic chemistry textbooks, where the Demjanov ring expansion reaction is called the Demjanov–Tiffeneau–Tchoubar rearrangement. This article aims at presenting the outstanding scientific legacy and turbulent life path of this researcher to the world scientific community. Маловідома на Батьківщині уродженка Харкова Б’янка Чубар зуміла створити справжню зміну парадигми у французькій органічній хімії XX століття. Оригінальністю наукових ідей, експериментальною майстерністю та непохитністю власних переконань ця науковиця здобула неабияке визнання у Франції та цілому світі. Ексцентрична парижанка українського походження стала першою жінкою, що увійшла до дослідницького штату Національного центру наукових досліджень Франції (Centre National de la Recherche Scientifique, CNRS) під час його створення 1939 року. Внесок науковиці у механістичні дослідження органічних реакцій, а також їх педагогічне опрацювання є неоціненними. Прізвище великої українки гордо майорить у французьких підручниках органічної хімії, які вшановують її експериментальні дослідження, називаючи реакцію розширення аліциклів, відому як перегрупування Дем’янова, перегрупуванням Дем’янова–Тіффано–Чубар. Пропонована стаття має на меті репрезентувати науковій спільноті України та світу видатні здобутки й непростий життєвий шлях цієї дослідниці. National University of Pharmacy 2022-07-20 Article Article application/pdf https://ophcj.nuph.edu.ua/article/view/255945 10.24959/ophcj.22.255945 Journal of Organic and Pharmaceutical Chemistry; Vol. 20 No. 2 (2022); 6-13 Журнал органической и фармацевтической химии; Том 20 № 2 (2022); 6-13 Журнал органічної та фармацевтичної хімії; Том 20 № 2 (2022); 6-13 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/255945/258017 Copyright (c) 2022 Romana-Iryna Yu. Martyniak http://creativecommons.org/licenses/by/4.0
spellingShingle механізми органічних реакцій
заряджені інтермедіати
сольові ефекти
молекулярні перегрупування
аліциклічні сполуки
історія хімії
Martyniak, Romana-Iryna Yu.
Б’янка Чубар – революціонерка французької органічної хімії
title Б’янка Чубар – революціонерка французької органічної хімії
title_alt Bianka Tchoubar: A Revolutionary in French Organic Chemistry
title_full Б’янка Чубар – революціонерка французької органічної хімії
title_fullStr Б’янка Чубар – революціонерка французької органічної хімії
title_full_unstemmed Б’янка Чубар – революціонерка французької органічної хімії
title_short Б’янка Чубар – революціонерка французької органічної хімії
title_sort б’янка чубар – революціонерка французької органічної хімії
topic механізми органічних реакцій
заряджені інтермедіати
сольові ефекти
молекулярні перегрупування
аліциклічні сполуки
історія хімії
topic_facet mechanisms of organic reactions
charged intermediates
salt effects
molecular rearrangements
alicyclic compounds
history of chemistry
механізми органічних реакцій
заряджені інтермедіати
сольові ефекти
молекулярні перегрупування
аліциклічні сполуки
історія хімії
url https://ophcj.nuph.edu.ua/article/view/255945
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