{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T16:16:37Z","timestamp":1785514597003,"version":"3.56.0"},"reference-count":200,"publisher":"Wiley","issue":"64","license":[{"start":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T00:00:00Z","timestamp":1634083200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,11,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The name of Menshutkin is most frequently associated with his eponymous reaction (the quaternization of tertiary amines with alkyl halides). However, he made encyclopedic contributions to the field of reaction kinetics, where he carried out extensive studies of the effects of reactant structure on the rates of esterification of monohydric, dihydric and trihydric alcohols with monocarboxylic acids, and monobasic and dibasic carboxylic acids and anhydrides with monohydric alcohols. In these studies, he deduced an order of reactivity of alcohols in esterification on the basis of their reactions with acetic acid, and the effects of acid structure on the rates of esterification based on the reaction of the carboxylic acid with isobutyl alcohol. When his attention later turned to the substitution chemistry of amines, he defined the parameters that affected their reactions: anilines were less reactive than alkylamines, secondary more reactive than primary amines, and the reaction was accelerated by replacing benzene as a solvent with alcohols. The wide\u2010ranging work of Menshutkin, the physical organic chemist, is discussed.<\/jats:p>","DOI":"10.1002\/chem.202101823","type":"journal-article","created":{"date-parts":[[2021,10,17]],"date-time":"2021-10-17T14:46:47Z","timestamp":1634482007000},"page":"15829-15841","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Early Physical Organic Chemistry: Nikolai Aleksandrovich Menshutkin (1842\u20131907) and Reaction Velocities"],"prefix":"10.1002","volume":"27","author":[{"given":"David E.","family":"Lewis","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Wisconsin-Eau Claire  Eau Claire WI 54702 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,10,13]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"Biographies of Menshutkin:"},{"key":"e_1_2_2_2_2","first-page":"278","volume":"39","author":"Tishchenko V. E.","year":"1907","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.190704004182"},{"key":"e_1_2_2_4_2","unstructured":"B.\u2005N. Menshutkin Zhizn i deyatel\u2032nost Nikolaya Aleksandra Menshutkina [The life and works of Nikolai Aleksandrovich Menshutkin] M. Frolova Press St. Petersburg 1908;"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19070201502"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1134\/S1070427207010351"},{"key":"e_1_2_2_6_3","first-page":"167","volume":"80","year":"2007","journal-title":"Zh. Prikl. Khim."},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/CT9119901646"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","unstructured":"Markovnikov's opinion: A.\u2005V. Zakharov Kazanskii universitet: khronologiya stanovleniyq khimicheskoi laboratorii i kazanskoi khimicheskoi shkoly. Chast I. 1806\u20131872 [Kazan University: Chronology of the Formation and Development of the Chemical Laboratory and Kazan Chemistry School. Part I. 1806\u20131872] Kazan University Kazan 2011 p. 740;"},{"key":"e_1_2_2_10_2","unstructured":"the same passage can be found in A.\u2005F. Plat\u00e9 G.\u2005V. Bykov M.\u2005S. Eventova Vladimir Vasil\u2032evich Markovnikov. Ocherk zhizni i deyatel\u2032nosti. 1837\u20131904 [Vladimir Vasil\u2032evich Markovnikov. An account of his life and activities. 1837\u20131904] Izd. Akad. Nauk Moscow 1962 pp. 43\u201346."},{"key":"e_1_2_2_11_1","unstructured":"Organicheskaya khimiya sostavlennaya po lektsiyam ord. prof. A.\u2005M. Butlerova stud. Iv. Bukhvostovym [Organic chemistry compiled from the lectures of Ord. Prof. A.\u2005M. Butlerov by student I. Bukhvostov]; Kazan lit. Kazan 1862\u20131863(298 pp)."},{"key":"e_1_2_2_12_1","unstructured":"A. Butlerov Vvedenie k polnomu izuchenie organicheskoi khimii [An Introduction to the Complete Study of Organic Chemistry] Izd. Fav-der-Flit Kazan 1864."},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","first-page":"273","volume":"10","author":"Sinin N.","year":"1842","journal-title":"Bull. Sci. Acad. Imp. Sci. St.-Petersbourg"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/prac.18420270125"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"crossref","first-page":"3","DOI":"10.70359\/bhc2016v041p003","volume":"41","author":"Lewis D. E.","year":"2016","journal-title":"Bull. Hist. Chem."},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201901922"},{"key":"e_1_2_2_19_1","unstructured":"Ref.\u2005[1c] p. 13 (English translation: File SUPP-TRANS-1)."},{"key":"e_1_2_2_20_1","unstructured":"Ref.\u2005[1c] p. 13 (English translation: File SUPP-TRANS-2)."},{"key":"e_1_2_2_21_1","unstructured":"Ref.\u2005[1c] p. 13 cites this letter as dated 15 February 1864."},{"key":"e_1_2_2_22_1","unstructured":"For accounts of the development of structural theory see:"},{"key":"e_1_2_2_23_2","unstructured":"O.\u2005T. Benfey From Vital Force to Structural Formulas Houghton Mifflin New York 1964;"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ed035p21"},{"key":"e_1_2_2_25_2","doi-asserted-by":"crossref","unstructured":"A.\u2005J. Rocke Image and Reality: Kekul\u00e9 Kopp and the Scientific Imagination The University of Chicago Press Chicago 2010;","DOI":"10.7208\/chicago\/9780226723358.001.0001"},{"key":"e_1_2_2_26_2","unstructured":"A.\u2005J. Rocke The Quiet Revolution University of California Press Berkeley 1993;"},{"key":"e_1_2_2_27_2","unstructured":"A.\u2005J. Rocke Origins in the Structural Theory of Organic Chemistry;Vols. 1\u20132; University of Wisconsin Press; Madison 1975;"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1017\/S0007087400018276"},{"key":"e_1_2_2_29_2","doi-asserted-by":"crossref","unstructured":"D.\u2005E. Lewis inAtoms in Chemistry: From Dalton's Predecessors to Complex Atoms and Beyond (Ed.: C. Giunta) ACS Symp. Ser.2010 1044 ch. 4 35\u201357;","DOI":"10.1021\/bk-2010-1044.ch004"},{"key":"e_1_2_2_30_2","doi-asserted-by":"crossref","first-page":"77","DOI":"10.70359\/bhc2019v044p077","volume":"44","author":"Lewis D. E.","year":"2019","journal-title":"Bull. Hist. 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Internat."},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","first-page":"98","volume":"3","author":"Kekul\u00e9 A.","year":"1865","journal-title":"Bull. Soc. Chim. Paris"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18661370202"},{"key":"e_1_2_2_41_1","unstructured":"\u00a0"},{"key":"e_1_2_2_42_2","unstructured":"N. Menschutkine Bull. Soc. Chim. Paris1864 2 122\u20131231864 241\u2013244;"},{"key":"e_1_2_2_43_2","unstructured":"N. Menschutkin C.\u2005R. Hebd. S\u00e9ances Acad. Sci.1864 59 295\u2013298;1865 60 532\u2013534."},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18661390309"},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","first-page":"217","volume":"29","author":"Kovalevskii V.","year":"1897","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_47_2","first-page":"223","volume":"29","author":"Yaroshenko A.","year":"1897","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_48_2","first-page":"30","volume":"31","author":"Podladchikov M.","year":"1899","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_49_2","first-page":"211","volume":"35","author":"Saks A.","year":"1903","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_50_1","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1007\/978-3-642-28219-5","volume-title":"Early Russian Organic Chemists and Their Legacy","author":"Lewis D. E.","year":"2012"},{"key":"e_1_2_2_51_1","unstructured":"\u201cO vodorode fosforistoi kisloty ne sposobnom k metallicheskomu zameshcheniyu pri obyknovennykh usloviyakh dlya kislot\u201d [\u201cAbout the hydrogen of phosphorous acid which is not capable of substitution by metals under ordinary conditions for acids\u201d] N. Menshutkin Magistr Khimiidissertation St. Petersburg University (Russia) 1866."},{"key":"e_1_2_2_52_1","unstructured":"\u00a0"},{"key":"e_1_2_2_53_2","first-page":"38","volume":"1","author":"Menshutkin N.","year":"1869","journal-title":"Zh. Russ. Khim. O-va."},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18701530104"},{"key":"e_1_2_2_55_1","unstructured":"\u201cSintez i svoystva ureidov\u201d [\u201cSynthesis and properties of ureides\u201d] N. Menshutkin Doktor Khimiidissertation St. Petersburg University (Russia) 1869."},{"key":"e_1_2_2_56_1","unstructured":"N. Menshutkin Analiticheskaya Khimiya [Analytical Chemistry] V. Demanov Press St. Petersburg 1st ed. 1871; 2nd ed. 1874; 3rd ed. 1877; 4th ed. 1880; 5th ed. 1883; 6th ed. 1888; 7th ed. 1894; 8th ed. 1897; 9th ed. 1901."},{"key":"e_1_2_2_57_1","unstructured":"D. Mendeleev Osnovy Khimii [Principles of Chemistry] St. Petersburg 1869."},{"key":"e_1_2_2_58_1","unstructured":"Analytische Chemie Deutsche Ausgabe unter Mitwirgung des Verfassers \u00fcbersetzt von Dr. O. Bach Quandt und Handel Leipzig 1st ed. 1877; 2nd ed. 1886; 3rd rev. ed. 1892."},{"key":"e_1_2_2_59_1","unstructured":"Analytical Chemistry N. Menschutkin. Translated from the third Germa\u043f edition under the supervisio\u043f of the author by James Locke Macmillan and Co. London 1895."},{"key":"e_1_2_2_60_1","unstructured":"Russian-language biographies of Butlerov:"},{"key":"e_1_2_2_61_2","first-page":"3","volume":"19","author":"Menshutkin N.","year":"1887","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_62_2","first-page":"13","volume":"19","author":"Zaitsev A.","year":"1887","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_63_2","first-page":"58","volume":"19","author":"Gustavson G.","year":"1887","journal-title":"Zh. Russ. Fiz.-Khim. 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An account of his life and activities. 1837\u20131904] Izd. Akad. Nauk Moscow 1962 pp. 43\u201346."},{"key":"e_1_2_2_71_1","unstructured":"Ref.\u2005[16] p. 71."},{"key":"e_1_2_2_72_1","unstructured":"\u00a0"},{"key":"e_1_2_2_73_2","unstructured":"A.\u2005S. Kluchevich G.\u2005V. Bykov Aleksandr Mikhailovich Zaitsev.1841\u20131910 Izd. Nauka Moscow 1980 p. 11;"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100215"},{"key":"e_1_2_2_75_2","doi-asserted-by":"crossref","first-page":"21","DOI":"10.70359\/bhc1995n17p021","volume":"17","author":"Lewis D. E.","year":"1995","journal-title":"Bull. Hist. Chem."},{"key":"e_1_2_2_76_1","doi-asserted-by":"publisher","DOI":"10.2307\/128008"},{"key":"e_1_2_2_77_1","unstructured":"Ref.\u2005[1c] footnote p. 21. (English translation: File Supp-4)."},{"key":"e_1_2_2_78_1","unstructured":"N. Menshutkin Lektsii Organicheskoi Khimii [Lectures in Organic Chemistry] St. Petersburg 1st ed. 1884; 2nd ed. 1891; 3rd ed. 1896; 4th ed. 1901."},{"key":"e_1_2_2_79_1","unstructured":"V.\u2005N. Ipatieff The Life of a Chemist. Memoirs of V.\u2005N. Ipatieff(Transl.: V. Haensel R.\u2005H. Lusher) Stanford University Press Stanford CA 1946."},{"key":"e_1_2_2_80_1","unstructured":"S.\u2005D. Kassow Students Professors and the State in Tsarist Russia University of California Press Berkeley 1989 Chapter\u20051."},{"key":"e_1_2_2_81_1","first-page":"404","volume":"26","author":"Menshutkin N.","year":"1894","journal-title":"Zh. Russ. Fiz.-Khim. O-va."},{"key":"e_1_2_2_82_1","unstructured":"\u00a0"},{"key":"e_1_2_2_83_2","unstructured":"M. Berthelot L. P\u00e9an\u2005de\u2005Saint-Gilles Ann. Chim. Phys.1862 65 385\u2013422;Ann. Chim. Phys.1862 66 5\u2013110;Ann. Chim. 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