/tory behind the /tory Was There a Conspiracy when Kekule's First German ~enzene-~tructuie Paper Was Frequently Listed as Published in 1865? John H. Wotiz and Susanna Rudofsky Southern Illinois University Carbondale, IL 62901
Citation errors always cause prohlems for literature searchers. When thev amear in a vublication of nreat hisRewrite Chemistry and its History" (I), it was pointed out that KekulB's first publication in the German language that deals with the stru&ure of henzene was " ~ n t e r s & & n g e n uber aromatische Verbindungen" (2) puhlished in 1866, and that this paper is frequently listed as published in 1865. Was this a deliberate plot by someone to avoid the two Kekul6 papers on this subject written in French in 1865 ( 3 , 4 )and that predate the German puhlication (2)? In 1890 the German Chemical Societv celebrated the 25th anniversary of Kekulb's discovery' (5).'Shaving off one year from the Annalen 137 vublication date (2) and suhstitutinr the German reference for the original French reference (37 would have made this Berlin "Fest" the celebration of a uniquely German discovery at a time when German nationalism was running high. A thorough search through the accounts, and the papers presented at this "Fest" (5),did not hear out the original suspicion. An account of the Berlin meeting in English hv Jaov also lists the correct oublication year fo;~nn. i37 (6):~n&hiitz's biography of ~ . = ~ e k u(7) l& and Walker's treatise ( 8 )on Kekuli: and the benzene vrohlem also list the correct date. In 1965 the American Chemical Society arranged a "Kekuli: Symposium," 0. T. Benfey Chairman, to celebrate the 100year anniversary of the Kekul6 proposal. The presented papers were published (91,and in the hook the Kekuli! Ann. 137 paper is cited by four authors correctly as published in 1866 (10). However, one author lists the incorrect year 1865 (11). As examples in the American literature this error can he also found in a journal article (12), in a source book (13), and a general history of chemistry textbook (14). Since the author
edited by JOHNH. WOTIZ Southern Illinois University Carbondale, Illinois 62901
of the textbook was also the coauthor of the source hook. an inquiry was made to ascertain the possible origin of the error. The author responded in part: "I must therefore accept the blame for introducing the error, which I hope arose as a misprint in the Sourcebook. I thought we had taken unusual pains with the citations in that volume, and I suppose I trusted i t for the 'Historical Backnround' " (15). However, we do not helieve that Professor ~eicesterintroduced this error. In 1872 Kekuli: puhlished the paper "Ueber einige Condensationproducte des Aldehyds" (see figure) (16). The second paragraph in this publication reads: "When I puhlished** for the first time in 1865 my views on the constitution of aromatic compounds. . . ." The two asterisks refer to the footnote on the same page which reads "Diese Annalen 137, 1 5 T 2 (see figure). A search of Liehig's Annalen of the 19th century shows that references in articles are given in footnotes which list the volume and the page, hut not the year of puhlication. This is suwvosed to he imvlicit in the volume number. I t may not have Glen obvious td Kekuli: and the editors of Annalen at the time that this could lead to a later misinterpretation of the puhlication date. I t may he asked why an article dealing with condensation products of aromatic aldehydes (16) led subsequent authors to misquote the Ann. 137 year. The answer may he suggested in an article by Hartmann: "The Benzene Structure. A Short History of a Prohlem" (17). The opening paragraph reads In the year 1866 August K e k d - a t that time a professor in Ghent-published two trealises dealing with aromatic compounds [ I ] . T h e first appeared in the B~dletind p la SociPtd Chimique and the second in Liehip Annalcn fur Chemistry and Pharmacy. In the Annalen work we find Cur the first time the well-known hexagon symbol but without the lines of double bonds. These appear for the first time in a third publication on aromatic compounds in the year 1872 [ Z ] .
'
Berlchf uber die Feier der Deotschen Chernischen Gesellschaff zur Ehren August Kekulh's. The article in Annalen 137 appears on pages 129 through 356.
Volume 59
Number 1 January 1982
23
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Literature Cited
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.
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16) Japp, F. R., J. Chem Soc., 13.97 (1898). 17) Anschlltz R.:A ' ugyst Kekul6." Vol. 1. Verlag Chemie. Berlin, 1929. I81 Walker.0.J.,Ann Sci., 1,34 (1939). (9) GouId.Rohert F.lEdilorl."KekulOCentennial".Advsnces in Chemistry Series, ACS
washington, D.C. H..p.70;Rose.N.C.,p.lO%Benfey,O.T..p. 121:Sehelar.V.M..
P U ~ I ~ C ~ ~ ~ O ~ S ,
(101 Ref. (91 Wi1cm.D. " ,m.,
& k h k dmtlcb. d a m . 0.rll.ab.
I h s Annuon 18?, 168;
The title page of KekulSs 1872 paper In Annalen( 16)
24
Reference I11 is our reference (3) and ( 2 ) with the incorrect year 1865. Reference [2] is our reference (16).The juxtaposition of the Ann. 137 (2) and Ann. 162 (16)articles leads us to believe that Hartmann obtained the incorrect date for Ann. 137 from KekulB's ambiguous citation in Ref. (16).The Ann. 162 paper (16)is by no means irrelevant to the theory of the benzene structure. I t contains a concise summary of Keku18's previous proposals and the first graphical representation by KekulB of double bonds in the hexagon. Ingold in his classical text of organic chemistry refers to the Ann. 162 article: "In 1872 Kekuk issued a supplementary hypothesis to the effect that an oscillation occurred between the two ~ o s s i h l earrangements h u h l e hand" (Id,. The questwn uf nhether Kekuli. was deliberately ambiyuuus in his Ann I62 citation cannot be answered without a search through editorial files and personal correspondence. We know thal thc participants i n the 1890 Herlin "Feat" (5) were not reluctant to cite the original two references written in French ( 3 , 4 ) .Laterday scholars may not have gone all the way to the citation source, hut they can be forgiven considering the circumstances.
Journal of Chemical Education
*mined. Loicestor. H. M.. "The Histo,iealBaekeround ofChemistrv."Isted.. Wilevandsonli ~ubli&ers, lks;Dover ~ ~ b ~ i New ~ ~ York t i ~ edition; ~ P 1971 , exs&ind, p. 188. 115) hicestor. H. M..Plivate comrnuniestian. MavP. 1980. I141
