Wrong but seminal

Publishing the wrong interpretation of experimental data can result in an immediate horde of chemists feeding on the error like vultures. On rare occasions, this phenomenon can open up an entire new field of science — and the structure of ferrocene is a case in point.

Access options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

Figure 1: Peter Pauson and Thomas J. Kealy published the first paper in the ferrocene timeline.
Figure 2: Proposed structures of dicyclopentadienyl iron.
Figure 3: R. B. Woodward and Geoffrey Wilkinson were the Harvard-based protagonists of the ferrocene story in the early 1950s.
Figure 4: A representation of the first publications of the key chemists studying the preparation, structure and properties of ferrocene and the connections between them.
Figure 5: Buckminsterfullerene and data from the 1985 Nature paper29 from Kroto and co-workers.
Figure 6: Robert K. Merton, an eminent sociologist of science who introduced concepts such as 'obliteration by incorporation' and the 'Matthew effect', both of which are relevant in the story of ferrocene.
Figure 7: Peter Pauson at the dinner table of E. O. Fischer, 1955.
Figure 8: R. B. Woodward plants the seeds of a potential scientific collaboration (that never came to fruition).

References

  1. 1

    Kealy, T. J. & Pauson, P. L. Nature 168, 1039–1040 (1951).

    CAS  Article  Google Scholar 

  2. 2

    Pauson, P. L. J. Organomet. Chem. 637639, 3–6 (2001).

    Article  Google Scholar 

  3. 3

    Pauson, P. L. Quart. Rev. Chem. Soc. 9, 391–414 (1955).

    CAS  Article  Google Scholar 

  4. 4

    Wilkinson, G. J. Organomet. Chem. 100, 273–278 (1975).

    CAS  Article  Google Scholar 

  5. 5

    Dunitz, J. D. Helv. Chim. Acta 96, 545–563 (2013).

    CAS  Article  Google Scholar 

  6. 6

    Dunitz, J. D. in Organic Chemistry: Its Language and Its State of the Art (ed. Kisakurek, V.) 9–23 (Wiley-VCH, 1993).

    Google Scholar 

  7. 7

    Laszlo, P. & Hoffmann, R. Angew. Chem. Int. Ed. 39, 123–124 (2000).

    CAS  Article  Google Scholar 

  8. 8

    Zydowsky, T. M. Chem. Intell. 6, 29–34 (2000).

    CAS  Google Scholar 

  9. 9

    Hoffmann, R. & Laszlo, P. Soc. Res. 65, 653–694 (1998).

    Google Scholar 

  10. 10

    Werner, H. Angew. Chem. Int. Ed. 53, 3309 (2014).

    CAS  Article  Google Scholar 

  11. 11

    Cantrill, S. in Milestones in Crystallography http://dx.doi.org/10.1038/nature13357 (2014).

    Google Scholar 

  12. 12

    Wilkinson, G., Rosenblum, M., Whiting, M. C. & Woodward, R. B. J. Am. Chem. Soc. 74, 2125–2126 (1952).

    CAS  Article  Google Scholar 

  13. 13

    Miller, S. A., Tebboth, J. A. & Tremaine, J. F. J. Chem. Soc. 632–635 (1952).

  14. 14

    Kauffman, G. B. J. Chem. Educ. 60, 185–186 (1983).

    CAS  Article  Google Scholar 

  15. 15

    Woodward, R. B., Rosenblum, M. & Whiting, M. C. J. Am. Chem. Soc. 74, 3458–3459 (1952).

    CAS  Article  Google Scholar 

  16. 16

    Cotton, F. A. & Wilkinson, G. J. Am. Chem. Soc. 74, 5764–5767 (1952).

    CAS  Article  Google Scholar 

  17. 17

    Page, J. A. & Wilkinson, G. J. Am. Chem. Soc. 74, 6149–6150 (1952).

    CAS  Article  Google Scholar 

  18. 18

    Wilkinson, G. J. Am. Chem. Soc. 74, 6146–6147 (1952).

    CAS  Article  Google Scholar 

  19. 19

    Wilkinson, G. J. Am. Chem. Soc. 74, 6148–6149 (1952).

    CAS  Article  Google Scholar 

  20. 20

    Seeman, J. I. J. Phys. Org. Chem. 27, 708–721 (2014).

    CAS  Article  Google Scholar 

  21. 21

    Fischer, E. O. & Pfab, W. Z. Naturforsch. B 7, 377–379 (1952).

    Article  Google Scholar 

  22. 22

    Eiland, P. F. & Pepinsky, R. J. Am. Chem. Soc. 74, 4971 (1952).

    CAS  Article  Google Scholar 

  23. 23

    Dunitz, J. D. & Orgel, L. E. Nature 171, 121–122 (1953).

    CAS  Article  Google Scholar 

  24. 24

    Richmond, H. H. & Freiser, H. J. Am. Chem. Soc. 77, 2022–2023 (1955).

    CAS  Article  Google Scholar 

  25. 25

    Jaffé, H. J. Chem. Phys. 21, 156–157 (1952).

    Article  Google Scholar 

  26. 26

    Moffitt, W. J. Am. Chem. Soc. 76, 3386–3392 (1954).

    CAS  Article  Google Scholar 

  27. 27

    Kaplan, L., Kester, W. J. & Katz, J. J. J. Am. Chem. Soc. 74, 5531–5532 (1952).

    CAS  Article  Google Scholar 

  28. 28

    Vale, R. D. Proc. Natl Acad. Sci. USA 112, 13439–13446 (2015).

    CAS  PubMed  Article  Google Scholar 

  29. 29

    Kroto, H., Heath, J. R., O'Brien, S. C., Curl, R. F. & Smalley, R. E. Nature 318, 162–163 (1985).

    CAS  Article  Google Scholar 

  30. 30

    Krätschmer, W., Lamb, L. D., Fostiropoulos, K. & Huffman, D. R. Nature 347, 354–358 (1990).

    Article  Google Scholar 

  31. 31

    Toumey, C. Nature Nanotech. 5, 693–694 (2010).

    CAS  Article  Google Scholar 

  32. 32

    Nature Nanotech. 5, 691 (2010).

  33. 33

    Sankey, H. Stud. Hist. Phil. Sci. 39, 259–264 (2008).

    Article  Google Scholar 

  34. 34

    Merton, R. K. Proc. Am. Phil. Soc. 105, 470–486 (1961).

    Google Scholar 

  35. 35

    Dunitz, J. D. & Orgel, L. E. J. Chem. Soc. 2594–2596 (1953).

  36. 36

    Merton, R. K. Isis 79, 606–623 (1988).

    Article  Google Scholar 

  37. 37

    Merton, R. K. Science 159, 56–63 (1968).

    PubMed  Article  PubMed Central  Google Scholar 

  38. 38

    Werner, H. Angew. Chem. Int. Ed. 51, 6052–6058 (2012).

    CAS  Article  Google Scholar 

  39. 39

    Merton, R. K. Soc. Forces 74, 379–424 (1995).

    Article  Google Scholar 

  40. 40

    Donahue, C. J. & Donahue, E. R. J. Chem. Educ. 90, 1688–1691 (2013).

    CAS  Article  Google Scholar 

  41. 41

    Nataro, C. & Fosbenner, S. M. J. Chem. Educ. 86, 1412–1415 (2009).

    CAS  Article  Google Scholar 

  42. 42

    Hwa, R. & Weizman, H. J. Chem. Educ. 84, 1497–1498 (2007).

    CAS  Article  Google Scholar 

  43. 43

    Birdwhistell, K. R., Nguyen, A., Ramos, E. J. & Kobelja, R. J. Chem. Educ. 85, 261–262 (2008).

    CAS  Article  Google Scholar 

  44. 44

    Woodward, R. B. & Doering, W. E. J. Am. Chem. Soc. 66, 849 (1944).

    Google Scholar 

  45. 45

    Doering, W. von E. & Detert, F. L. J. Am. Chem. Soc. 73, 876–877 (1951).

    CAS  Article  Google Scholar 

  46. 46

    Dewar, M. J. S. Nature 155, 50–51 (1945).

    CAS  Article  Google Scholar 

  47. 47

    Nozoe, T. in Seventy Years in Organic Chemistry (ed. Seeman, J. I.) (Profiles, Pathways, and Dreams series, American Chemical Society, 1991).

    Google Scholar 

  48. 48

    Wilkinson, G., Pauson, P. L. & Cotton, F. A. J. Am. Chem. Soc. 76, 1970–1974 (1954).

    CAS  Article  Google Scholar 

  49. 49

    Pauson, P. L. & Wilkinson, G. J. Am. Chem. Soc. 76, 2024–2026 (1954).

    CAS  Article  Google Scholar 

  50. 50

    Wilkinson, G., Pauson, P. L., Birmingham, J. M. & Cotton, F. A. J. Am. Chem. Soc. 75, 1011–1012 (1953).

    CAS  Article  Google Scholar 

  51. 51

    Graening, T. & Schmalz, H.-G. Angew. Chem. Int. Ed. 43, 3230–3256 (2004).

    CAS  Article  Google Scholar 

  52. 52

    Bentley, R. J. Chem. Educ. 81, 1462–1470 (2004).

    CAS  Article  Google Scholar 

  53. 53

    Sayre, D. & Frazer, B. C. J. Appl. Crystal. 28, 245–246 (1995).

    Article  Google Scholar 

  54. 54

    Battersby, A. R. in Further Perspectives in Organic Chemistry (ed. Lord Todd) 50 (Elsevier, 1978).

    Google Scholar 

  55. 55

    Barton, D. H. R. Some Recollections of Gap Jumping (ed. Seeman, J. I.) (Profiles, Pathways, and Dreams series, American Chemical Society, 1991).

    Google Scholar 

  56. 56

    Quack, M. Angew. Chem. Int. Ed. 52, 2–11 (2013).

    Article  CAS  Google Scholar 

  57. 57

    Laszlo, P. Angew. Chem. Int. Ed. 39, 2071–2072 (2000).

    CAS  Article  Google Scholar 

Download references

Acknowledgements

We thank a number of journal editors for sharing their criteria for publication, including A. Padwa and S. Rychnovsky (The Journal of Organic Chemistry). J.I.S. thanks W. Myers (University of Richmond) and R. Wheeler (Duquesne University) for being catalysts for this project and the Harvard University Archives for their hospitality. We also thank O. T. Benfey, J. Dunitz, A. Eschenmoser, J. Gal, G. S. Girolami, R. Hoffmann, H. Kroto, P. Laszlo and W. Myers for helpful discussions. We dedicate this paper to the memory of Robert K. Merton (1910–2003). Today, many of his concepts, three of which are discussed in this manuscript and others, such as 'role model', 'self-fulfilling prophecy' and 'unintended consequences', are so much a part of today's lexicon that his inventorship of them is relatively unknown according to his own concept, 'obliteration by incorporation'.

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Jeffrey I. Seeman or Stuart Cantrill.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Seeman, J., Cantrill, S. Wrong but seminal. Nature Chem 8, 193–200 (2016). https://doi.org/10.1038/nchem.2455

Download citation

Further reading