An Investigation into the Role and Importance of Three-Dimensional Representations through an Analysis of Late 19th and Early 20th Century Chemistry Textbooks

Published 2025-06-19
Keywords
- three-dimensional representations,
- symbolic level,
- chemistry manuals,
- tetrahedral carbon,
- metal complexes
How to Cite
Copyright (c) 2025 Matteo Chioccioli

This work is licensed under a Creative Commons Attribution 4.0 International License.
Abstract
Graphic representations of three-dimensional structures play a pivotal role both in academic research and chemical education. Nevertheless, their deceptive simplicity can lead school and even university students to an incorrect understanding of these representations that are central for both organic and inorganic chemistry. A deep knowledge of their symbolic meaning is, indeed, essential to avoid a meaningless learning of the discipline.
Two important historical examples, the three-dimensional representations of tetrahedral carbon and the geometry of metal complexes, are discussed in this paper. More in detail, this work investigates the way in which these three-dimensional formulae were received and presented in school and university textbooks published in the late 19th and early 20th centuries, before the introduction of techniques of structural investigation such as X-ray crystallography. Given the difficulty of finding all textbooks published in that period worldwide, the creation of a freely accessible database is also encouraged. Generally underestimated in historical investigations, old chemistry manuals are, in fact, essential to understand how the discipline has been taught in the past.
References
- A. H. Johnstone, Macro- and micro-chemistry., Sch. Sci. Rev. 1982, 64, 377-379.
- A. H. Johnstone, Why is science difficult to learn? Things are seldom what they seem., J. Comput. Assist. Learn. 1991, 7, 75-83.
- A. H. Johnstone, The development of chemistry teaching: a changing response to changing demand., J. Chem. Educ. 1993, 70, 701-705.
- A. H. Johnstone, You can’t get there from here., J. Chem. Educ. 2010, 87, 22-29.
- N. Reid, A tribute to Professor Alex H. Johnstone (1930–2017): His unique contribution to chemistry education research. Chem. Teacher Int. 2019, 1(1), 1-13.
- A. H. Johnstone, Teaching of Chemistry: logical or psychological?, Chem. Educ. Res. Pract. 2000, 1, 9-15.
- P. Mahaffy, The future shape of chemistry education., Chem. Educ. Res. Pract. 2004, 5(3), 229−245.
- P. Mahaffy, Moving chemistry education in 3D, a tetrahedral metaphor for understanding chemistry., J. Chem. Educ. 2006, 83, 49-55.
- J. Sjöström, I. Eilks, V. Talanquer, Didaktik Models in Chemistry Education., J. Chem. Educ. 2020, 97(4), 910-915.
- J. Sjöström, Towards Bildung-oriented chemistry education., Science and Education 2013, 22, 1873-1890.
- J. Sjöström, I. Eilks, Reconsidering different visions of scientific literacy and science education based on the concept of Bildung. In Cognition, Metacognition, and Culture in STEM Education: Learning, Teaching and Assessment, Springer International Publishing, 2018, pp 65-88.
- S. J. Weininger, Contemplating the Finger: Visuality and the Semiotics of Chemistry., HYLE – Int. J. Phil. Chem. 1998, 4, 3-27.
- R. Hoffmann, P. Laszlo, Representation in Chemistry., Angew. Chem. Int. Ed. 1991, 30, 1-16.
- K. S. Taber, Learning at the symbolic level. Chapter 4, in J. K. Gilbert & D. F. Treagust (Eds.), Multiple Representations in Chemical Education, Dordrecht: Springer, 2009, pp.75-108.
- Google Books: https://books.google.it
- WorldCat - An international library catalog: https://search.worldcat.org/it
- Internet Archive - An American nonprofit digital library: https://archive.org/
- OPAC-SBN - On-line public access catalog – Italian National Library Service: https://opac.sbn.it
- BNF-Gallica - The Online Digital Library of the Bibliothèque Nationale de France: https://gallica.bnf.fr
- J. H. van’t Hoff, Voorstel tot uitbreiding der tegenwoordig in de scheikunde gebruikte structuur-formules in de ruimte; benevens een daarmeê samenhangende opmerking omtrent het verband tusschen optisch actief vermogen en chemische constitutie van organische verbindingen, J. Greven, Utrecht, 1874.
- J. H. van’t Hoff, Sur les formules de structure dans l‘espace., Arch. Neerl. Sci. Exactes Nat. 1874, 9, 445-454.
- J. A. Le Bel, Sur les relations qui existent entre les formules atomiques des corps organique et le pouvoir rotatoire de leurs dissolutions., Bull. Soc. Chim. Fr. 1874, 22, 337-347.
- J. H. van’t Hoff, Sur les formules de structure dans l‘espace., Bull. Soc. Chim. Fr. 1875, 23, 295-301.
- J. H. van’t Hoff, La Chimie dans l’espace, P. M. Bazendijk, Rotterdam, 1875.
- J. H. van’t Hoff, Die Lagerung der Atome im Raume, Druck und Verlag von Friedrich Vieweg und Sohn, Braunschweig, 1877.
- J. Wislicenus, Ueber die isomeren Milchsäure. Zweite Abhandlung. XXV. Ueber die optisch- active Milchsäure der Fleisch-flüssigkeit, die Paramilchsäure., Annalen der Chemie und Pharmacie 1873, 167, 302-346.
- O. B. Ramsay, The origins of stereochemistry: the contributions of J. H. van’t Hoff and J. A. Le Bel. Chapter 5, in Stereochemistry. Nobel Prize Topics in Chemistry: A Series of Historical Monographs on Fundamental Chemistry, Heyden, London, Philadelphia, Rheine, 1981, pp. 81-97.
- J. H. van’t Hoff, Dix années dans l’histoire d’une théorie (Deuxième édition de La chimie dans l’espace), P. M. Bazendijk, Rotterdam, 1887.
- J. H. van't Hoff, Chemistry in Space, Clarendon Press, Oxford, 1891.
- G. M. Richardson, translated and edited by. The Foundations of Stereo Chemistry. Memoirs by Pasteur, van’t Hoff, Le Bel, and Wislicenus. American Book Company, New York, Cincinnati, Chicago, 1901.
- R. B. Grossman, Van’t Hoff, Le Bel, and the Development of Stereochemistry: A Reassessment., J. Chem. Educ. 1989, 66(1), 30-33.
- T. Benfey, A. Travis, Carl Schorlemmer: the Red Chemist., Chemistry and Industry 1992, 12, 441-444.
- C. Schorlemmer, The rise and development of organic chemistry, J. E. Cornish, Manchester; Simkin, Marshall & Co., London, 1879.
- J. Wislicenus, Über die räumliche Anordnung der Atome in organischen Molekülen und ihre Bestimmung in geometrisch-isomeren ungesättigten Verbindungen, in Abhandlungen der K. Sächsischen Gesellschaft der Wissenschaften, 1887, 14, 1. An English translation of this work can be found in ref [30], pp. 61-132.
- W. P. Palmer, Nineteenth Century British and American Chemistry Textbook Writers: Some Differences of Approach. Proceedings of the Fourth Annual Educational Research Symposium of the Northern Territory Institute of Educational Research (NTIER), Northern Territory University, Darwin, 2001, pp. 27-47.
- H. E. Roscoe, C. Schorlemmer, A Treatise on Chemistry (4 Volumes). Volume III. The Chemistry of the Hydrocarbons and their Derivatives or Organic Chemistry. Part I, MacMillan & Co., London, 1881.
- H. E. Roscoe, C. Schorlemmer, A Treatise on Chemistry (4 Volumes). Volume III. The Chemistry of the Hydrocarbons and their Derivatives or Organic Chemistry. Part II, MacMillan & Co., London, 1884.
- I. Remsen, An Introduction to the study of the compounds of carbon; or, organic chemistry, Ginn, Heath & Co., Boston, 1885.
- I. Remsen, Principles of Theoretical Chemistry, with special reference to the constitution of chemical compounds, Herry C. Lea., Philadelphia, first edition, 1877; second Edition, 1883; third edition, 1887.
- F. Sestini, A. Funaro, Corso di chimica ad uso delle scuole secondarie., Raffaello Giusti Editore, Livorno, sixth edition, 1901; seventh edition, edited by Prof. Q. Sestini , 1905; eight edition, second edited by Prof. Q. Sestini, 1907; ninth edition, third edited by Prof. Q. Sestini, 1909; tenth edition, fourth edited by Prof. Q. Sestini, 1912; eleventh edition, fifth edited by Prof. Q. Sestini, 1914; twelfth edition, sixth edited by Prof. Q. Sestini, 1918; thirteenth edition, seventh edited by Prof. Q. Sestini, 1921; fourteenth edition, eighth edited by Prof. Q. Sestini, [pref. 1921].
- P. Levi, Il Sistema periodico, Einaudi, Turin, 1915, p. 27.
- A. Baeyer, Ueber Polyacetylenverbindungen., Berichte 1885, 18, 2269-2281.
- A. Werner, Beitrag zur Konstitution anorganischer Verbindungen., Z. Anorg. Chem. 1893, 3, 267-330.
- A. Werner, Neuere Anschauungen auf dem Gebiete der Anorganischen Chemie, Vieweg und Sohn, Braunscweing, 1905.
- H. Berke, Old and New ‘Anschauungen in der Anorganischen Chemie’. A Homage to Alfred Werner’s Book and Intuition. Part I. Alfred Werner’s Book and Coordination Theory., Chimia 2009, 63, 541-544.
- G. S. Newth, A Textboook of Inorganic Chemistry, Longmans, Green, & Co., London, New York, Bombay and Calcutta, first edition, 1894; eleventh edition, 1905.
- A. R. Hantzsch, Grundiss der Stereochemie, Verlag von Eduard Trewendt, Breslau, 1893.
- A. R. Hantzsch, Précis de stéréochimie, traduction française publiée par M. Ph.-A Guye et M. Gautier; avec une note additionnelle de A. Werner, Georges Carré, éditeur, Paris, 1896.
- A. R. Hantzsch, The elements of stereochemistry, translated from the French edition of Guye and Gautier by Charles G. L. Wolf, The Chemical Publishing Company, Easton, 1901.
- J. H. van’t Hoff, The arrangement of atoms in space. Second revised and enlarged edition. Longman, Green, & Co., London, New York, Bombay and Calcutta, 1898.
- A. Werner, A. Miolati, Beiträge zur Konstitution anorganischer Verbindungen, I Abhandlung., Z. Phys. Chem., 1893, 12, 35-55.
- A. F. Holleman, Leerboek der anorganiche Chemie, J. B. Wolters, Groningen, 1898.
- A. F. Holleman, Lehrbuch der anorganischen Chemie für Studierende an Universitäten und Technischen Hochschulen (bearbeitet und herausgegeben von Wilhelm Manchot), Verlag von Veit & Comp., Leipzig, 1900; Zweite Verbesserte Auflage, 1903; Dritte Auflage, 1905.
- A. F. Holleman, A Text-book of Inorganic Chemistry, rendered into English by H. C. Cooper with the co-operation of the author, John Wiley & Sons, New York, 1902; second edition, 1905; third edition, 1908.
- A. W. Stewart, Stereochemistry, Longmans, Green, & Co., London, New York, Bombay and Calcutta, 1907.