641:, 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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779:
681:, 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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539:, 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).
665:
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
503:
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
409:
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
572:. 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,
684:
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
801:, 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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610:, 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
535:. 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
1520:. 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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630:), 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
531:" or "bonds"), was based largely on evidence from chemical reactions, rather than on instrumental methods that could peer directly into the molecule, such as
594:. 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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991:"Ueber die Constitution und die Metamorphosen der chemischen Verbindungen und über die chemische Natur des Kohlenstoffs"
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797:, giving him the right to add "von Stradonitz" to his name, referring to a possession of his patrilineal ancestors in
430:. After graduating from secondary school (the Grand Ducal Gymnasium in Darmstadt), in the fall of 1847 he entered the
385:. 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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474:, where he remained for the rest of his career. Basing his ideas on those of predecessors such as Williamson,
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447:
1432:
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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1177:"Ueber einige Condensationsproducte des Aldehyds (On some condensation products of aldehydes)"
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1125:"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
446:, Switzerland (1852–53), and in London (1853–55), where he was decisively influenced by
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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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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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945:. Vol. 15 (11th ed.). Cambridge University Press. pp. 717–718.
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434:, 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
828:. His statue is often humorously decorated by students, e.g. for
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450:. 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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677:(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,
281:
Ueber die Amyloxydschwefelsäure und einige ihrer Salze
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Foreign associates of the National Academy of Sciences
645:, who replaced Kekulé's oscillation by the concept of
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350:
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718:(in German). Vol. 2. Erlangen: Enke. 1862–1866.
708:(in German). Vol. 1. Erlangen: Enke. 1859–1861.
378:[ˈfʁiːdʁɪçˈʔaʊɡʊstˈkeːkuleːfɔnʃtʁaˈdoːnɪts]
341:
51:. Unsourced material may be challenged and removed.
568:Kekulé's most famous work was on the structure of
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1220:International Journal for Philosophy of Chemistry
897:
466:. In 1858, he was hired as full professor at the
381:; 7 September 1829 – 13 July 1896), was a German
2015:
768:(in German). Vol. 7. Stuttgart: Enke. 1887.
758:(in German). Vol. 6. Stuttgart: Enke. 1882.
748:(in German). Vol. 5. Stuttgart: Enke. 1881.
738:(in German). Vol. 4. Stuttgart: Enke. 1880.
389:. He was the principal founder of the theory of
1551:"Kekule von Stradonitz, Friedrich August"
1490:. University of Chicago Press. pp. 60–66.
1264:Proceedings of the National Academy of Sciences
728:(in German). Vol. 3. Erlangen: Enke. 1867.
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422:The son of a civil servant, Kekulé was born in
2089:Recipients of the Pour le Mérite (civil class)
1406:Berichte der Deutschen Chemischen Gesellschaft
1159:Berichte der Deutschen Chemischen Gesellschaft
1093:"Untersuchungen uber aromatische Verbindungen"
679:Berichte der Deutschen Chemischen Gesellschaft
675:Berichte der Durstigen Chemischen Gesellschaft
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885:Random House Webster's Unabridged Dictionary
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1469:Mémoires de l'Académie Royale de Belgique
1338:. Courier Corporation. pp. 179–180.
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111:Learn how and when to remove this message
2064:Academic staff of the University of Bonn
1074:Bulletin de la Société Chimique de Paris
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1157:(Observations on the aromatic theory),
649:between quantum-mechanical structures.
2016:
1881:Friedrich August Kekulé von Stradonitz
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1155:"Bemerkungen zur aromatischen Theorie"
809:, Kekulé's former students won three:
333:Friedrich August Kekule von Stradonitz
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2074:Foreign members of the Royal Society
2044:People from the Grand Duchy of Hesse
1527:(University of Chicago Press, 2010).
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49:adding citations to reliable sources
20:
1257:"The Shared-Electron Chemical Bond"
1024:"Sur une nouvelle théorie chimique"
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1313:from the original on 11 March 2020
16:German organic chemist (1829–1896)
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1544:Kekulé: A Scientist and a Dreamer
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1181:Annalen der Chemie und Pharmacie
1098:Annalen der Chemie und Pharmacie
1029:Annales de chimie et de physique
996:Annalen der Chemie und Pharmacie
963:Annalen der Chemie und Pharmacie
936:"Kekulé, Friedrich August"
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1051:. University of Chicago Press.
765:Lehrbuch der Organischen Chemie
755:Lehrbuch der Organischen Chemie
745:Lehrbuch der Organischen Chemie
735:Lehrbuch der Organischen Chemie
725:Lehrbuch der Organischen Chemie
715:Lehrbuch der Organischen Chemie
705:Lehrbuch der Organischen Chemie
414:pronounced the third syllable.
36:needs additional citations for
2069:Recipients of the Copley Medal
1557:New International Encyclopedia
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1517:Journal of Chemical Education
1434:Journal of Chemical Education
1360:Journal of Chemical Education
1131:. 28 May 2015. Archived from
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803:Stephan Kekule von Stradonitz
2059:University of Giessen alumni
2034:19th-century German chemists
1214:Pierre Laszlo (April 2004).
454:Theory of chemical structure
305:Jacobus Henricus van 't Hoff
7:
1540:(Kekulé's dream, in German)
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1825:Jean-Baptiste Boussingault
1801:August Wilhelm von Hofmann
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2039:Scientists from Darmstadt
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1419:10.1002/cber.189002301204
1386:10.1080/00033798500200411
1335:From Alchemy to Chemistry
1153:Ladenburg, Albert (1869)
807:Nobel Prizes in Chemistry
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464:University of Heidelberg
261:University of Heidelberg
2049:German organic chemists
1769:Julius Robert von Mayer
1187:(2–3). Wiley: 309–320.
1175:Kekulé, August (1872).
942:Encyclopædia Britannica
602:X, where X = Cl, OH, CH
458:In 1856, Kekulé became
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329:Friedrich August Kekulé
146:Friedrich August Kekulé
1841:James Joseph Sylvester
1657:Michel Eugène Chevreul
1617:Alexander von Humboldt
1486:Alan J. Rocke (2010).
1047:Alan J. Rocke (2010).
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634:isomers respectively.
577:Archibald Scott Couper
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501:Archibald Scott Couper
393:and in particular the
219:Tetravalence of carbon
1945:George Gabriel Stokes
1849:Charles Adolphe Wurtz
1785:Hermann von Helmholtz
1753:Henri Victor Regnault
1633:Johannes Peter Müller
1625:Heinrich Wilhelm Dove
1285:10.1073/pnas.14.4.359
795:Wilhelm II of Germany
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632:ortho, meta, and para
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533:X-ray crystallography
492:Charles-Adolphe Wurtz
432:University of Giessen
426:, the capital of the
387:theoretical chemistry
205:University of Giessen
1929:Stanislao Cannizzaro
1897:Joseph Dalton Hooker
1761:James Prescott Joule
1673:Wilhelm Eduard Weber
1399:Aug. Kekulé (1890).
1362:, 42 (1965), 266–67.
1129:worldofchemicals.com
1091:Aug. Kekulé (1866).
1022:A.S. Couper (1858).
989:Aug. Kekulé (1858).
956:Aug. Kekulé (1857).
805:. Of the first five
789:In 1895, Kekulé was
514:Alexander Crum Brown
448:Alexander Williamson
428:Grand Duchy of Hesse
309:Hermann Emil Fischer
164:Grand Duchy of Hesse
45:improve this article
2001:Marcellin Berthelot
1993:John William Strutt
1977:Albert von Kölliker
1905:Thomas Henry Huxley
1889:Franz Ernst Neumann
1737:Karl Ernst von Baer
1649:Henri Milne-Edwards
1446:1958JChEd..35...21B
1332:Read, John (1957).
1276:1928PNAS...14..359P
1135:on 10 November 2022
846:Non-Kekulé molecule
691:horse-drawn omnibus
468:University of Ghent
265:University of Ghent
1745:Charles Wheatstone
1401:"Benzolfest: Rede"
880:"Kekulé's formula"
826:University of Bonn
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585:aromatic compounds
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522:Alexander Butlerov
391:chemical structure
269:University of Bonn
216:chemical structure
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1817:James Dwight Dana
1596:Copley Medallists
1497:978-0-226-72332-7
1374:Annals of Science
1345:978-0-486-28690-7
1058:978-0-226-72332-7
911:978-1-4831-4523-5
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60:"August Kekulé"
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30:
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2031:
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1997:
1989:
1981:
1973:
1969:Carl Gegenbaur
1965:
1957:
1949:
1941:
1937:Rudolf Virchow
1933:
1925:
1917:
1909:
1901:
1893:
1885:
1877:
1869:
1861:
1853:
1845:
1837:
1829:
1821:
1813:
1809:Claude Bernard
1805:
1797:
1789:
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1765:
1757:
1749:
1741:
1733:
1729:Julius Plücker
1725:
1721:Michel Chasles
1717:
1713:Charles Darwin
1709:
1701:
1693:
1685:
1677:
1669:
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1532:External links
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1523:Rocke, A. J.,
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1413:(1): 1302–11.
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1270:(4): 359–362.
1253:Pauling, Linus
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933:, ed. (1911).
931:Chisholm, Hugh
917:
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643:Linus Pauling
640:
635:
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588:
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582:
578:
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571:
562:
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549:periodic acid
546:
540:
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537:Hermann Kolbe
534:
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221:Structure of
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186:German Empire
183:
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127:August Kekulé
124:
115:
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93:
90:
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79:
76:
72:
69:
65:
62: –
61:
57:
56:Find sources:
50:
46:
40:
39:
34:This article
32:
28:
23:
22:
19:
1880:
1609:Richard Owen
1555:
1524:
1515:
1487:
1481:
1472:
1468:
1462:
1440:(1): 21–23.
1437:
1433:
1427:
1410:
1404:
1394:
1377:
1373:
1367:
1359:
1354:
1334:
1327:
1315:. Retrieved
1267:
1263:
1247:
1235:. Retrieved
1223:
1219:
1209:
1184:
1180:
1170:
1162:
1158:
1149:
1137:. Retrieved
1133:the original
1128:
1119:
1102:
1096:
1086:
1080:(2): 98–110.
1077:
1073:
1067:
1048:
1042:
1033:
1027:
1017:
1000:
994:
984:
967:
961:
951:
940:
904:. Elsevier.
900:
893:
883:
875:
823:
817:in 1902 and
788:
764:
754:
744:
734:
724:
714:
704:
687:
683:
678:
674:
672:
664:
636:
589:
579:in 1858 and
574:
567:
541:
526:
496:tetravalence
460:Privatdozent
457:
421:
408:
332:
328:
327:
280:
257:Institutions
250:
238:Copley Medal
176:(1896-07-13)
174:13 July 1896
107:
98:
88:
81:
74:
67:
55:
43:Please help
38:verification
35:
18:
2029:1896 deaths
2024:1829 births
1873:Carl Ludwig
1598:(1851–1900)
1317:29 November
1226:(1). Hyle.
811:van 't Hoff
418:Early years
193:Nationality
2018:Categories
1475:(1): 1–40.
1036:: 488–489.
867:References
799:Stradonice
793:by Kaiser
612:toluidines
214:Theory of
152:1829-09-07
71:newspapers
1232:1433-5158
1201:0075-4617
834:Halloween
821:in 1905.
813:in 1901,
668:ouroboros
647:resonance
506:Frankland
424:Darmstadt
160:Darmstadt
101:June 2015
1308:Archived
1304:16587350
840:See also
791:ennobled
529:valences
331:, later
243:ForMemRS
1560:. 1905.
1442:Bibcode
1295:1085493
1272:Bibcode
1139:2 March
815:Fischer
784:benzene
592:isomers
570:benzene
556:Benzene
462:at the
440:Giessen
399:benzene
374:German:
369:-kə-lay
223:benzene
85:scholar
2003:(1900)
1995:(1899)
1987:(1898)
1979:(1897)
1971:(1896)
1963:(1895)
1955:(1894)
1947:(1893)
1939:(1892)
1931:(1891)
1923:(1890)
1915:(1889)
1907:(1888)
1899:(1887)
1891:(1886)
1883:(1885)
1875:(1884)
1867:(1883)
1859:(1882)
1851:(1881)
1843:(1880)
1835:(1879)
1827:(1878)
1819:(1877)
1811:(1876)
1803:(1875)
1795:(1874)
1787:(1873)
1779:(1872)
1771:(1871)
1763:(1870)
1755:(1869)
1747:(1868)
1739:(1867)
1731:(1866)
1723:(1865)
1715:(1864)
1707:(1863)
1699:(1862)
1691:(1861)
1683:(1860)
1675:(1859)
1667:(1858)
1659:(1857)
1651:(1856)
1643:(1855)
1635:(1854)
1627:(1853)
1619:(1852)
1611:(1851)
1494:
1342:
1302:
1292:
1237:6 July
1230:
1199:
1055:
908:
819:Baeyer
774:Honors
520:, and
285:(1852)
283:
276:Thesis
245:(1875)
240:(1885)
235:(1893)
229:Awards
196:German
87:
80:
73:
66:
58:
1311:(PDF)
1260:(PDF)
697:Works
510:Wurtz
92:JSTOR
78:books
1492:ISBN
1340:ISBN
1319:2020
1300:PMID
1239:2013
1228:ISSN
1197:ISSN
1141:2018
1053:ISBN
906:ISBN
626:)(CH
606:, NH
472:Bonn
444:Chur
405:Name
182:Bonn
171:Died
142:Born
64:news
1450:doi
1415:doi
1382:doi
1290:PMC
1280:doi
1189:doi
1185:162
1107:doi
1103:137
1005:doi
1001:106
972:doi
968:104
832:or
670:).
622:(NH
614:, C
397:of
367:KAY
47:by
2020::
1554:.
1473:37
1471:.
1448:.
1438:35
1436:.
1411:23
1409:.
1403:.
1378:42
1376:.
1306:.
1298:.
1288:.
1278:.
1268:14
1266:.
1262:.
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1222:.
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1179:.
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1127:.
1101:.
1095:.
1076:.
1034:53
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999:.
993:.
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960:.
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920:^
882:.
836:.
524:.
516:,
512:,
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490:,
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478:,
401:.
372:,
357:eɪ
354:əl
348:eɪ
184:,
162:,
1588:e
1581:t
1574:v
1500:.
1456:.
1452::
1444::
1421:.
1417::
1388:.
1384::
1348:.
1321:.
1282::
1274::
1241:.
1203:.
1191::
1163:2
1143:.
1113:.
1109::
1078:3
1061:.
1011:.
1007::
978:.
974::
914:.
888:.
628:3
624:2
620:4
618:H
616:6
608:2
604:3
600:5
598:H
596:6
360:/
351:k
345:k
342:ˈ
339:/
335:(
154:)
150:(
114:)
108:(
103:)
99:(
89:·
82:·
75:·
68:·
41:.
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