652:, a former student of Kekulé, who argued that Kekulé's 1865 structure implied two distinct "ortho" structures, depending on whether the substituted carbons are separated by a single or a double bond. Since ortho derivatives of benzene were never actually found in more than one isomeric form, Kekulé modified his proposal in 1872 and suggested that the benzene molecule oscillates between two equivalent structures, in such a way that the single and double bonds continually interchange positions. This implies that all six carbon-carbon bonds are equivalent, as each is single half the time and double half the time. A firmer theoretical basis for a similar idea was later proposed in 1928 by
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790:
692:, only the parody had six monkeys seizing each other in a circle, rather than a single snake as in Kekulé's anecdote. Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well-known through oral transmission even if it had not yet appeared in print. Others have speculated that Kekulé's story in 1890 was a re-parody of the monkey spoof, and was a mere invention rather than a recollection of an event in his life.
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550:, heavily criticized the use of structural formulas that were offered, as he thought, without proof. However, most chemists followed Kekulé's lead in pursuing and developing what some have called "classical" structure theory, which was modified after the discovery of electrons (1897) and the development of quantum mechanics (in the 1920s).
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The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry after 1865 that in 1890 the German
Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene
514:
independently arrived at the idea of self-linking of carbon atoms (his paper appeared in June 1858), and provided the first molecular formulas where lines symbolize bonds connecting the atoms. For organic chemists, the theory of structure provided dramatic new clarity of understanding, and a reliable
420:
Kekulé never used his first given name; he was known throughout his life as August Kekulé. After he was ennobled by the Kaiser in 1895, he adopted the name August Kekule von
Stradonitz, without the French acute accent over the second "e". The French accent had apparently been added to the name by
583:. In 1865 Kekulé published a paper in French (for he was then still in Belgium) suggesting that the structure contained a six-membered ring of carbon atoms with alternating single and double bonds. The following year he published a much longer paper in German on the same subject.
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The idea that the number of valences of a given element was invariant was a key component of Kekulé's version of structural chemistry. This generalization suffered from many exceptions, and was subsequently replaced by the suggestion that valences were fixed at certain
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guide to both analytic and especially synthetic work. As a consequence, the field of organic chemistry developed explosively from this point. Among those who were most active in pursuing early structural investigations were, in addition to Kekulé and Couper,
695:
Kekulé's 1890 speech, in which these anecdotes appeared, has been translated into
English. If one takes the anecdote as reflecting an accurate memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.
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He told another autobiographical anecdote in the same 1890 speech, of an earlier vision of dancing atoms and molecules that led to his theory of structure, published in May 1858. This happened, he claimed, while he was riding on the upper deck of a
812:, Bohemia. His name thus became Friedrich August Kekule von Stradonitz, without the French accent on the last "e" of his name, and this is the form of the name that some libraries use. This title was inherited by his son, genealogist
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paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail (this is an ancient symbol known as the
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according to Kekuléan structure theory could be represented by the chain structure I-O-O-O-O-H. By contrast, the modern structure of (meta) periodic acid has all four oxygen atoms surrounding the iodine in a tetrahedral geometry.
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of carbon (which Kekulé announced late in 1857) and the ability of carbon atoms to link to each other (announced in a paper published in May 1858), to the determination of the bonding order of all of the atoms in a molecule.
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Kekulé's idea of assigning certain atoms to certain positions within the molecule, and schematically connecting them using what he called their "Verwandtschaftseinheiten" ("affinity units", now called "
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in London. Once again, if one takes the anecdote as reflecting an accurate memory of a real event, circumstances related in the anecdote suggest that it must have occurred in the late summer of 1855.
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621:, etc.) only one isomer was ever found, implying that all six carbons are equivalent, so that substitution on any carbon gives only a single possible product. For diderivatives such as the
546:. Such physical methods of structural determination had not yet been developed, so chemists of Kekulé's day had to rely almost entirely on so-called "wet" chemistry. Some chemists, notably
1531:. Volume 35, No. 1, January 1958. p. 21–23. – Includes an English translation of Kekule's 1890 speech in which he spoke about his development of structure theory and benzene theory.
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641:), three isomers were observed, for which Kekulé proposed structures with the two substituted carbon atoms separated by one, two and three carbon-carbon bonds, later named
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and others, Kekulé was the principal formulator of the theory of chemical structure (1857–58). This theory proceeds from the idea of atomic valence, especially the
542:" or "bonds"), was based largely on evidence from chemical reactions, rather than on instrumental methods that could peer directly into the molecule, such as
605:. Kekulé argued for his proposed structure by considering the number of isomers observed for derivatives of benzene. For every monoderivative of benzene (C
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A larger-than-life monument of Kekulé, unveiled in 1903, is situated in front of the former
Chemical Institute (completed 1868) at the
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was in its earliest years, and too little evidence was then available to help chemists decide on any particular structure.
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The empirical formula for benzene had been long known, but its highly unsaturated structure was a challenge to determine.
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1002:"Ueber die Constitution und die Metamorphosen der chemischen Verbindungen und über die chemische Natur des Kohlenstoffs"
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808:, giving him the right to add "von Stradonitz" to his name, referring to a possession of his patrilineal ancestors in
441:. After graduating from secondary school (the Grand Ducal Gymnasium in Darmstadt), in the fall of 1847 he entered the
396:. From the 1850s until his death, Kekulé was one of the most prominent chemists in Europe, especially in the field of
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in 1861 suggested possible structures that contained multiple double bonds or multiple rings, but the study of
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485:, where he remained for the rest of his career. Basing his ideas on those of predecessors such as Williamson,
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O. T. Benfey (1958). "August Kekulé and the Birth of the
Structural Theory of Organic Chemistry in 1858".
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Benfey, O. Theodor. "August Kekule and the Birth of the
Structural Theory of Organic Chemistry in 1858."
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Kekulé's benzene ring in modern form, and the alchemical ouroboros symbol of a snake eating its tail
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and a brief compulsory military service, he took temporary assistantships in Paris (1851–52), in
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1188:"Ueber einige Condensationsproducte des Aldehyds (On some condensation products of aldehydes)"
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1136:"Friedrich August Kekule von Stradonitz –inventor of benzene structure – World Of Chemicals"
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More evidence was available by 1865, especially regarding the relationships of aromatic
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in his first semester, he decided to study chemistry. Following four years of study in
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Jean Gillis (1966). "Auguste Kekulé et son oeuvre, realisee a Gand de 1858 a 1867".
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Kekulé's father during the
Napoleonic occupation of Hesse by France, to ensure that
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969:"Über die s. g. gepaarten Verbindungen und die Theorie der mehratomigen Radicale"
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1964 West German centenary stamp for the discovery of the molecular formula of
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The counting of possible isomers for diderivatives was, however, criticized by
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956:. Vol. 15 (11th ed.). Cambridge University Press. pp. 717–718.
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445:, with the intention of studying architecture. After hearing the lectures of
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A.J. Rocke (1985). "Hypothesis and
Experiment in Kekulé's Benzene Theory".
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Organic
Chemistry: The Name Game: Modern Coined Terms and Their Origins
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Aug. Kekulé (1865). "Sur la constitution des substances aromatiques".
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Corresponding members of the Saint
Petersburg Academy of Sciences
839:. His statue is often humorously decorated by students, e.g. for
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461:. His Giessen doctoral degree was awarded in the summer of 1852.
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Image and Reality: Kekule, Kopp, and the Scientific Imagination
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Image and Reality: Kekulé, Kopp, and the Scientific Imagination
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Image and Reality: Kekulé, Kopp, and the Scientific Imagination
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688:(Journal of the Thirsty Chemical Society), a parody of the
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Another depiction of benzene had appeared in 1886 in the
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Kekulé structure of benzene with alternating double bonds
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Nickon, Alex; Silversmith, Ernest F. (22 October 2013).
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Translated into English by D. Wilcox and F. Greenbaum,
292:
Ueber die Amyloxydschwefelsäure und einige ihrer Salze
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Foreign associates of the National Academy of Sciences
656:, who replaced Kekulé's oscillation by the concept of
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361:
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729:(in German). Vol. 2. Erlangen: Enke. 1862–1866.
719:(in German). Vol. 1. Erlangen: Enke. 1859–1861.
389:[ˈfʁiːdʁɪçˈʔaʊɡʊstˈkeːkuleːfɔnʃtʁaˈdoːnɪts]
352:
62:. Unsourced material may be challenged and removed.
579:Kekulé's most famous work was on the structure of
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1231:International Journal for Philosophy of Chemistry
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477:. In 1858, he was hired as full professor at the
392:; 7 September 1829 – 13 July 1896), was a German
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779:(in German). Vol. 7. Stuttgart: Enke. 1887.
769:(in German). Vol. 6. Stuttgart: Enke. 1882.
759:(in German). Vol. 5. Stuttgart: Enke. 1881.
749:(in German). Vol. 4. Stuttgart: Enke. 1880.
400:. He was the principal founder of the theory of
1562:"Kekule von Stradonitz, Friedrich August"
1501:. University of Chicago Press. pp. 60–66.
1275:Proceedings of the National Academy of Sciences
739:(in German). Vol. 3. Erlangen: Enke. 1867.
464:
433:The son of a civil servant, Kekulé was born in
2100:Recipients of the Pour le Mérite (civil class)
1417:Berichte der Deutschen Chemischen Gesellschaft
1170:Berichte der Deutschen Chemischen Gesellschaft
1104:"Untersuchungen uber aromatische Verbindungen"
690:Berichte der Deutschen Chemischen Gesellschaft
686:Berichte der Durstigen Chemischen Gesellschaft
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896:Random House Webster's Unabridged Dictionary
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1480:Mémoires de l'Académie Royale de Belgique
1349:. Courier Corporation. pp. 179–180.
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122:Learn how and when to remove this message
2075:Academic staff of the University of Bonn
1085:Bulletin de la Société Chimique de Paris
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1168:(Observations on the aromatic theory),
660:between quantum-mechanical structures.
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1892:Friedrich August Kekulé von Stradonitz
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1166:"Bemerkungen zur aromatischen Theorie"
820:, Kekulé's former students won three:
344:Friedrich August Kekule von Stradonitz
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2085:Foreign members of the Royal Society
2055:People from the Grand Duchy of Hesse
1538:(University of Chicago Press, 2010).
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60:adding citations to reliable sources
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1268:"The Shared-Electron Chemical Bond"
1035:"Sur une nouvelle théorie chimique"
24:
1519:
1324:from the original on 11 March 2020
27:German organic chemist (1829–1896)
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1555:Kekulé: A Scientist and a Dreamer
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1192:Annalen der Chemie und Pharmacie
1109:Annalen der Chemie und Pharmacie
1040:Annales de chimie et de physique
1007:Annalen der Chemie und Pharmacie
974:Annalen der Chemie und Pharmacie
947:"Kekulé, Friedrich August"
481:, then in 1867 he was called to
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1062:. University of Chicago Press.
776:Lehrbuch der Organischen Chemie
766:Lehrbuch der Organischen Chemie
756:Lehrbuch der Organischen Chemie
746:Lehrbuch der Organischen Chemie
736:Lehrbuch der Organischen Chemie
726:Lehrbuch der Organischen Chemie
716:Lehrbuch der Organischen Chemie
425:pronounced the third syllable.
47:needs additional citations for
2080:Recipients of the Copley Medal
1568:New International Encyclopedia
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1528:Journal of Chemical Education
1445:Journal of Chemical Education
1371:Journal of Chemical Education
1142:. 28 May 2015. Archived from
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814:Stephan Kekule von Stradonitz
2070:University of Giessen alumni
2045:19th-century German chemists
1225:Pierre Laszlo (April 2004).
465:Theory of chemical structure
316:Jacobus Henricus van 't Hoff
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1551:(Kekulé's dream, in German)
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1836:Jean-Baptiste Boussingault
1812:August Wilhelm von Hofmann
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2050:Scientists from Darmstadt
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1430:10.1002/cber.189002301204
1397:10.1080/00033798500200411
1346:From Alchemy to Chemistry
1164:Ladenburg, Albert (1869)
818:Nobel Prizes in Chemistry
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1020:10.1002/jlac.18581060202
987:10.1002/jlac.18571040202
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475:University of Heidelberg
272:University of Heidelberg
2060:German organic chemists
1780:Julius Robert von Mayer
1198:(2–3). Wiley: 309–320.
1186:Kekulé, August (1872).
953:Encyclopædia Britannica
613:X, where X = Cl, OH, CH
469:In 1856, Kekulé became
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340:Friedrich August Kekulé
157:Friedrich August Kekulé
18:Friedrich August Kekulé
1852:James Joseph Sylvester
1668:Michel Eugène Chevreul
1628:Alexander von Humboldt
1497:Alan J. Rocke (2010).
1058:Alan J. Rocke (2010).
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645:isomers respectively.
588:Archibald Scott Couper
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512:Archibald Scott Couper
404:and in particular the
230:Tetravalence of carbon
1956:George Gabriel Stokes
1860:Charles Adolphe Wurtz
1796:Hermann von Helmholtz
1764:Henri Victor Regnault
1644:Johannes Peter Müller
1636:Heinrich Wilhelm Dove
1296:10.1073/pnas.14.4.359
806:Wilhelm II of Germany
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643:ortho, meta, and para
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544:X-ray crystallography
503:Charles-Adolphe Wurtz
443:University of Giessen
437:, the capital of the
398:theoretical chemistry
216:University of Giessen
1940:Stanislao Cannizzaro
1908:Joseph Dalton Hooker
1772:James Prescott Joule
1684:Wilhelm Eduard Weber
1410:Aug. Kekulé (1890).
1373:, 42 (1965), 266–67.
1140:worldofchemicals.com
1102:Aug. Kekulé (1866).
1033:A.S. Couper (1858).
1000:Aug. Kekulé (1858).
967:Aug. Kekulé (1857).
816:. Of the first five
800:In 1895, Kekulé was
525:Alexander Crum Brown
459:Alexander Williamson
439:Grand Duchy of Hesse
320:Hermann Emil Fischer
175:Grand Duchy of Hesse
56:improve this article
2012:Marcellin Berthelot
2004:John William Strutt
1988:Albert von Kölliker
1916:Thomas Henry Huxley
1900:Franz Ernst Neumann
1748:Karl Ernst von Baer
1660:Henri Milne-Edwards
1457:1958JChEd..35...21B
1343:Read, John (1957).
1287:1928PNAS...14..359P
1146:on 10 November 2022
857:Non-Kekulé molecule
702:horse-drawn omnibus
479:University of Ghent
276:University of Ghent
1756:Charles Wheatstone
1412:"Benzolfest: Rede"
891:"Kekulé's formula"
837:University of Bonn
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596:aromatic compounds
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533:Alexander Butlerov
402:chemical structure
280:University of Bonn
227:chemical structure
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1828:James Dwight Dana
1607:Copley Medallists
1508:978-0-226-72332-7
1385:Annals of Science
1356:978-0-486-28690-7
1069:978-0-226-72332-7
922:978-1-4831-4523-5
447:Justus von Liebig
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306:Justus von Liebig
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558:. For example,
529:Emil Erlenmeyer
499:Auguste Laurent
467:
431:
423:French-speakers
418:
394:organic chemist
384:
377:
351:
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212:Alma mater
199:
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117:
111:
108:
71:"August Kekulé"
65:
63:
53:
41:
28:
23:
22:
15:
12:
11:
5:
2113:
2103:
2102:
2097:
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2077:
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2067:
2062:
2057:
2052:
2047:
2042:
2037:
2020:
2019:
2017:
2016:
2008:
2000:
1992:
1984:
1980:Carl Gegenbaur
1976:
1968:
1960:
1952:
1948:Rudolf Virchow
1944:
1936:
1928:
1920:
1912:
1904:
1896:
1888:
1880:
1872:
1864:
1856:
1848:
1840:
1832:
1824:
1820:Claude Bernard
1816:
1808:
1800:
1792:
1784:
1776:
1768:
1760:
1752:
1744:
1740:Julius Plücker
1736:
1732:Michel Chasles
1728:
1724:Charles Darwin
1720:
1712:
1704:
1696:
1688:
1680:
1672:
1664:
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1557:
1552:
1544:
1543:External links
1541:
1540:
1539:
1534:Rocke, A. J.,
1532:
1521:
1518:
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1507:
1489:
1470:
1435:
1424:(1): 1302–11.
1402:
1375:
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1335:
1281:(4): 359–362.
1264:Pauling, Linus
1255:
1217:
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1127:
1116:(2): 129–196.
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1075:
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992:
981:(2): 129–150.
959:
944:, ed. (1911).
942:Chisholm, Hugh
928:
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901:
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867:Kekulé Program
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664:Kekulé's dream
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1868:Arthur Cayley
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1549:Kekulés Traum
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654:Linus Pauling
651:
646:
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560:periodic acid
557:
551:
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548:Hermann Kolbe
545:
541:
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232:Structure of
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155:
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138:August Kekulé
135:
126:
123:
115:
104:
101:
97:
94:
90:
87:
83:
80:
76:
73: –
72:
68:
67:Find sources:
61:
57:
51:
50:
45:This article
43:
39:
34:
33:
30:
19:
1891:
1620:Richard Owen
1566:
1535:
1526:
1498:
1492:
1483:
1479:
1473:
1451:(1): 21–23.
1448:
1444:
1438:
1421:
1415:
1405:
1388:
1384:
1378:
1370:
1365:
1345:
1338:
1326:. Retrieved
1278:
1274:
1258:
1246:. Retrieved
1234:
1230:
1220:
1195:
1191:
1181:
1173:
1169:
1160:
1148:. Retrieved
1144:the original
1139:
1130:
1113:
1107:
1097:
1091:(2): 98–110.
1088:
1084:
1078:
1059:
1053:
1044:
1038:
1028:
1011:
1005:
995:
978:
972:
962:
951:
915:. Elsevier.
911:
904:
894:
886:
834:
828:in 1902 and
799:
775:
765:
755:
745:
735:
725:
715:
698:
694:
689:
685:
683:
675:
647:
600:
590:in 1858 and
585:
578:
552:
537:
507:tetravalence
471:Privatdozent
468:
432:
419:
343:
339:
338:
291:
268:Institutions
261:
249:Copley Medal
187:(1896-07-13)
185:13 July 1896
118:
109:
99:
92:
85:
78:
66:
54:Please help
49:verification
46:
29:
2040:1896 deaths
2035:1829 births
1884:Carl Ludwig
1609:(1851–1900)
1328:29 November
1237:(1). Hyle.
822:van 't Hoff
429:Early years
204:Nationality
2029:Categories
1486:(1): 1–40.
1047:: 488–489.
878:References
810:Stradonice
804:by Kaiser
623:toluidines
225:Theory of
163:1829-09-07
82:newspapers
1243:1433-5158
1212:0075-4617
845:Halloween
832:in 1905.
824:in 1901,
679:ouroboros
658:resonance
517:Frankland
435:Darmstadt
171:Darmstadt
112:June 2015
1319:Archived
1315:16587350
851:See also
802:ennobled
540:valences
342:, later
254:ForMemRS
1571:. 1905.
1453:Bibcode
1306:1085493
1283:Bibcode
1150:2 March
826:Fischer
795:benzene
603:isomers
581:benzene
567:Benzene
473:at the
451:Giessen
410:benzene
385:German:
380:-kə-lay
234:benzene
96:scholar
2014:(1900)
2006:(1899)
1998:(1898)
1990:(1897)
1982:(1896)
1974:(1895)
1966:(1894)
1958:(1893)
1950:(1892)
1942:(1891)
1934:(1890)
1926:(1889)
1918:(1888)
1910:(1887)
1902:(1886)
1894:(1885)
1886:(1884)
1878:(1883)
1870:(1882)
1862:(1881)
1854:(1880)
1846:(1879)
1838:(1878)
1830:(1877)
1822:(1876)
1814:(1875)
1806:(1874)
1798:(1873)
1790:(1872)
1782:(1871)
1774:(1870)
1766:(1869)
1758:(1868)
1750:(1867)
1742:(1866)
1734:(1865)
1726:(1864)
1718:(1863)
1710:(1862)
1702:(1861)
1694:(1860)
1686:(1859)
1678:(1858)
1670:(1857)
1662:(1856)
1654:(1855)
1646:(1854)
1638:(1853)
1630:(1852)
1622:(1851)
1505:
1353:
1313:
1303:
1248:6 July
1241:
1210:
1066:
919:
830:Baeyer
785:Honors
531:, and
296:(1852)
294:
287:Thesis
256:(1875)
251:(1885)
246:(1893)
240:Awards
207:German
98:
91:
84:
77:
69:
1322:(PDF)
1271:(PDF)
708:Works
521:Wurtz
103:JSTOR
89:books
1503:ISBN
1351:ISBN
1330:2020
1311:PMID
1250:2013
1239:ISSN
1208:ISSN
1152:2018
1064:ISBN
917:ISBN
637:)(CH
617:, NH
483:Bonn
455:Chur
416:Name
193:Bonn
182:Died
153:Born
75:news
1461:doi
1426:doi
1393:doi
1301:PMC
1291:doi
1200:doi
1196:162
1118:doi
1114:137
1016:doi
1012:106
983:doi
979:104
843:or
681:).
633:(NH
625:, C
408:of
378:KAY
58:by
2031::
1565:.
1484:37
1482:.
1459:.
1449:35
1447:.
1422:23
1420:.
1414:.
1389:42
1387:.
1317:.
1309:.
1299:.
1289:.
1279:14
1277:.
1273:.
1235:10
1233:.
1229:.
1206:.
1190:.
1172:,
1138:.
1112:.
1106:.
1087:.
1045:53
1043:.
1037:.
1010:.
1004:.
977:.
971:.
950:.
931:^
893:.
847:.
535:.
527:,
523:,
519:,
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493:,
489:,
412:.
383:,
368:eɪ
365:əl
359:eɪ
195:,
173:,
1599:e
1592:t
1585:v
1511:.
1467:.
1463::
1455::
1432:.
1428::
1399:.
1395::
1359:.
1332:.
1293::
1285::
1252:.
1214:.
1202::
1174:2
1154:.
1124:.
1120::
1089:3
1072:.
1022:.
1018::
989:.
985::
925:.
899:.
639:3
635:2
631:4
629:H
627:6
619:2
615:3
611:5
609:H
607:6
371:/
362:k
356:k
353:ˈ
350:/
346:(
165:)
161:(
125:)
119:(
114:)
110:(
100:·
93:·
86:·
79:·
52:.
20:)
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