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On the Density of Racemic and Homochiral Crystals: Wallach, Liebisch and Sommerfeld in Göttingen

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On the Density of Racemic and Homochiral Crystals: Wallach, Liebisch and Sommerfeld in Göttingen CHIRALITY – SYmmeTRIeS And ASYmmeTRIeS CHIMIA 2018, 72, No. 6 399 doi:10.2533/chimia.2018.399 Chimia 72 (2018) 399–403 © Swiss Chemical Society On the Density of Racemic and Homochiral Crystals: Wallach, Liebisch and Sommerfeld in Göttingen Karl-Heinz Ernst*ab Dedicated to Prof. Jack Dunitz on the occasion of his 95th birthday. In memoriam of Howard Flack Abstract: The first comparison of heterochiral crystals with their homochiral counterparts was given by Otto Wallach in an account on carvone bromide crystals in 1895 in Liebigs Annalen der Chemie. Although the well- known mineralogist Theodor Liebisch, professor in Göttingen from 1887 to 1908, performed the analyses and wrote the last four pages of that Annalen paper, his colleague from chemistry, Wallach served as sole author. We discuss whether Wallach or Liebisch had the idea of a comparative study of crystal densities of racemates and their homochiral analogues and who of the two should be credited. Keywords: Arnold Sommerfeld · Chiral crystallization · History of science · Otto Wallach · Theodor Liebisch the Swiss Federal Laboratories for an essay about this small episode of the Materials Science and Technology. In history of science,[9] it was Wallach’s col- 1995 he founded the Molecular Surface league Theodor Liebisch, professor of Science Group, specializing in chirality of mineralogy in Göttingen, who performed two-dimensional molecular crystals, func- and reported on the density of crystals tional surfaces and single molecule surface of chiral compounds in the Wallach- dynamics. He was visiting researcher at authored Annalen paper. In the same pa- the Physics Department of UC Berkeley, per, which even contains measurements at the Department of Bioengineering at the performed by Arnold Sommerfeld, both University of Washington in Seattle and at Wallach and Liebisch claimed to be the IBM Almaden Research Center, San José, father of the idea of such comparative Born in Northeim near Göttingen in CA. Currently he holds an adjunct faculty studies. Although it was common at that Lower Saxony, Germany, Karl-Heinz position at the Department of Chemistry at time not to have students and assistants Ernst was originally trained as Chemical the University of Zurich and was recently listed as coauthors, it is quite interesting Technical Assistant (CTA). He studied promoted at Empa to Distinguished Senior to speculate why Wallach did not include Chemical Engineering and Chemistry at Scientist. his colleague as a coauthor. the TFH Berlin and the Freie Universität Berlin, respectively. His PhD studies were conducted at the Berlin Electron Storage 1. Introduction 2. Otto Wallach (1847–1931) Ring for Synchrotron Radiation (BESSY I) and the Freie Universität Berlin. After a In 1895 Otto Wallach published as Otto Wallach was born (27.3.1847) postdoctoral research stay at the University sole author a paper entitled ‘Zur Kenntnis in Königsberg, East Prussia, and grew of Washington in Seattle he joined Empa, der Terpene und der ätherischen Oele; up in Potsdam near Berlin (Fig. 1). Due No. 34: Ueber gebromte Derivate der to health problems, he had a bad start in Carvonreihe’,[1] in Justus Liebigs Annalen school,[10] but became a good student later. der Chemie 286, pp. 119–143.[2] One im- His friend Georg Borsche introduced him portant result of the paper is the evalua- to chemistry and Wallach followed him tion of the density of racemate crystals in 1867 to Göttingen to study chemistry with respect to their homochiral counter- under Friedrich Wöhler. He spent one se- parts. For eight of the nine tested samples, mester inbetween in Berlin with August *Correspondence: Prof. Dr. K.-H. Ernstab E-mail: [email protected] higher densities (up to 4%) were reported Wilhelm von Hofmann (1818–1892), who aEmpa – Swiss Federal Laboratories for Materials for the racemate crystals. The empirical had just come from London as Eilhard Science and Technology finding, namely, that racemic crystals Mitscherlich’s (1794–1863) successor. Laboratory for Nanoscale Materials Science Überlandstrasse 125 tend to have a higher density than their Wallach completed his PhD after only CH-8600 Dübendorf homochiral analogues, was coined later five semesters! In his doctorate work bDepartment of Chemistry ‘Wallach’s rule’,[3] an expression which (‘Über von Toluol abgeleitete neue iso- University of Zurich Winterthurerstrasse 190 has subsequently often been used in the mere Verbindungen’) under the direction CH-8057 Zürich literature.[4–8] As published previously in of Hans Hübner, he isolated an unknown 400 CHIMIA 2018, 72, No. 6 CHIRALITY – SYmmeTRIeS And ASYmmeTRIeS isomer of bromotoluene by crystallization. Although a true finding, it was disputed by ab Wöhler’s assistant Fittig, who offered his head if Wallach were right. (“Der Wallach will ein neues Bromtoluol gefunden haben! Ich lege meinen Kopf auf diesen Tisch und Sie können ihn abhauen, wenn das richtig ist.”[11] “Wallach claims discovery of a new bromotoluene! I will lay down my head onto this table and you may decollate it, if this is correct.”). Wallach was happy to leave Göttingen in 1869, “with the quiet and genuine desire: never to be seen there again.”[11] As Fig. 1 Fig. 1. a) Otto Wallach, Nobel Laureate in Chemistry 1910. b) Wallach is buried at the shows, it turned out differently. Wallach Stadtfriedhof in Göttingen among seven other Nobel laureates and many famous scientists and became assistant of Hermann Wichelhaus mathematicians. in Berlin and worked with August Kekulé in Bonn. After voluntary service in the German-French war, he went to Agfa in on terpenes until his retirement in 1915. bromides and aims at elucidation of their Berlin, but returned to Bonn again to work Wallach was very active even after his molecular structure by analyzing chemical with Kekulé and achieved his Habilitation. retirement and remained a bachelor his and physical properties. Besides the puz- As professor for pharmacy in Bonn, entire life. He was appointed already in zling role Liebisch plays in that paper, it Wallach began his seminal terpene work. 1885 fellow of the Deutsche Akademie contains several other remarkable com- Wallach described later as cause for his in- der Naturforscher Leopoldina, which ponents (Fig. 2). Concerning conglomer- terest in ethereal oils, flasks on a cupboard awarded him – long before Emil Fischer – ate versus racemate crystallization, the in Kekulé’s private laboratory containing with its prestigious Cothenius Medal. most important part is described in the such substances, but being untouched for As fellow of the Prussian Academy of chapter ‘Ueber racemie’ (About race- fifteen years. Wallach’s request to perform Sciences, Wallach became decorated with mism). Wallach repeatedly emphasizes research on their content were granted by more medals by Prussia. His colleagues in the importance of studies on racemism, Kekulé with ironical laughter: “Yes, if you England elected him as Honorary Fellow “because complete darkness prevails can make anything out of them!”[12] of the Chemical Society and awarded him about the principles in which such trans- In the 1880s research on terpenes the Honorary Doctor of the University of formations occur”; and “a solution to this had been lacking a systematic approach. Manchester. He received honorary doctor- question is only expected when numerous Wallach: “...if one casts a glance over the ates from the University of Leipzig and suitable examples are studied”. Wallach old literature of the terpenes, it does not the Institute of Technology Braunschweig. compares physical properties, like melt- appear a particularly enticing subject for (Even a crater on the moon was named ing and boiling points as well as crystal investigation. There were isolated obser- after him in 1979). Wallach was awarded shape, of optically active bromocarvones vations in almost incomprehensible abun- with the Nobel Prize in Chemistry 1910 with their inactive modifications (Fig. 2). dance.”[13] Or in the words of Leopold and learned about it from a newspaper on He particularly points out that he, in con- Ružicˇka (1887–1976, Chemistry Nobel the train from Hannover to Göttingen.[15] trast to others, believes in the importance laureate 1939): “…Wallach had plunged of synthesizing optically active as well as into work in a neglected garden so over- inactive crystalline counterparts. Wallach run with weeds that the useful plants could 3. Wallach’s Annalen from 1895 also made a side blow at Emil Fischer, not thrive. Any good gardeners had al- who ignored[16] Wallach’s discussion on ready attempted to improve its condition, The work reported in the Annalen pa- racemism ([My work has] “... not received but each had soon damaged his hands and per from 1895 serves as a good example the slightest attention” Wallach writes in a the weeds had begun to flourish again with for Wallach’s approach.[1] He describes the footnote of ref. [1]). renewed vigor. […] After about the begin- bromination of carvone and dihydrocar- Wallach clearly points out that there ning of 1890, the garden was well weeded vone, reports their tri-, tetra-, and penta- are exceptions from the tendency that ra- and it soon enticed other gardeners to investigate the conditions of life and the Fig. 2. Collection of properties of the plants, and to determine melting points and [12] their species.” crystal forms of race- Wallach reported in 1888 that dipentene mic and enantiopure is nothing but the racemic mixture of limo- carvone bromides. nene enantiomers,[14] and managed to iso- late (–)-limonene from spruce needle oil. As already had been applied in his doctoral work, Wallach brominated the compounds and achieved thus products that could be readily crystallized. As with Liebisch later in Göttingen, he involved a mineralogist (Carl Adolf Ferdinand Hintze, 1851–1916) in his analyses. When Victor Meyer went to Heidelberg in 1889 to replace Bunsen, Wallach succeeded him and went back to Göttingen, where he continued his work CHIRALITY – SYmmeTRIeS And ASYmmeTRIeS CHIMIA 2018, 72, No.
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