Controversy in chemistry: What counts as evidence? Two studies in molecular structure

Angewandte Chemie - International Edition

Volumn 43, Issue 20, 2004, Pages 2612-2619

  Labinger, Jay A ^a   Weininger, Steve J ^b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b WORCESTER POLYTECHNIC INSTITUTE   (United States)

Author keywords

History of science; Isomers; Stereochemistry; Structure elucidation

Indexed keywords

CRYSTAL STRUCTURE; ISOMERIZATION; MOLECULAR STRUCTURE; STEREOCHEMISTRY;

BOND-STRETCH ISOMERIZATION; CRYSTAL STRUCTURE ANALYSIS;

MOLECULAR DYNAMICS;

ATOM; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMER; ISOMERIZATION; MOLECULE; PROCESS DEVELOPMENT; RELIABILITY; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 4544259073     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200330055     Document Type: Review

References (72)

1. a) P. Machamer, M. Pera, A. Baltas, Scientific Controversies: Philosophical and Historical Perspectives, Oxford University Press, New York, 2000;
2. b) T. Brante, S. Fuller, W. Lynch, Controversial Science: From Content to Contention, State University of New York, Albany, 1993;
3. c) Scientific Controversies: Case Studies in the Resolution and Closure of Disputes in Science and Technology (Eds.: H. T. Engelhardt, Jr., A. L. Caplan), Cambridge University Press, Cambridge, 1987.
4. Others have recognized this inadequacy as well; there are already imaginative efforts underway to repair it, aimed at children in elementary and secondary schools, for example, Project SCOPE http://scope.educ.washington.edu, retrieved 24 December 2002 from the Worldwide Web.
5. Partial support by the Dreyfus Foundation is gratefully acknowledged, as is the encouragement of its former director, Dr. Robert Lichter.
6. Jerome Berson, Chemical Discovery and the Logician's Program: A Problematic Pairing, Wiley-VCH, Weinheim, 2003.
7. R. Hoffmann, P. Laszlo, Angew. Chem. 2001, 113, 4733-4739; Angew. Chem. Int. Ed. 2001, 40, 4599-4604.
8. R. Hoffmann, P. Laszlo, Angew. Chem. 2001, 113, 4733-4739; Angew. Chem. Int. Ed. 2001, 40, 4599-4604.
9. P. Laszlo, R. Hoffmann, Angew. Chem. 2000, 112, 127-128; Angew. Chem. Int. Ed. 2000, 39, 123-124.
10. P. Laszlo, R. Hoffmann, Angew. Chem. 2000, 112, 127-128; Angew. Chem. Int. Ed. 2000, 39, 123-124.
11. R. Hoffmann, V. I. Minkin, B. K. Carpenter, Bull. Soc. Chim. Fr. 1996, 133, 117-130.
12. T. S. Kuhn, The Essential Tension: Selected Studies in Scientific Tradition and Change, University of Chicago Press, Chicago, [1959] 1977, p. 229.
13. D. Pestre in his review of M. Fortun, H. J. Bernstein, Muddling Through: Pursuing Science and Truths in the 21st Century, Counterpoint, Washington, DC, 1998, retrieved 9 July 2002 from the Worldwide Web: http://physicsweb.org/ article/review/13/3/3.
14. D. R. Herschbach in The Flight from Science and Reason (Eds.: P.R. Gross, N. Levitt, M. W. Lewis), New York Academy of Sciences, New York, 1997, p. 17.
15. Project 2061: Science for All Americans, American Association for the Advancement of Science, Washington, DC, 1989.
16. D. M. Knight, J. Chem. Educ. 1971, 48, 285-286.
17. a) J. A. Le Bel, Bull. Soc. Chim. Fr. Ser. 2 1874, 22, 337-347;
18. b) H. van't Hoff, Voorstel tot uitbreding der tegenwoordig in de scheikundegebruikte structur-formules in de ruimte: ..., J. Greven, Utrecht, 1874; J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat. 1874, 9, 445-454; P. J. Ramberg, G. J. Somsen, Ann. Sci. 2001, 58, 51-74 (this article provides a new English translation of the Voorstel and also discusses the proper spelling of van't Hoff's surname);
19. b) H. van't Hoff, Voorstel tot uitbreding der tegenwoordig in de scheikundegebruikte structur-formules in de ruimte: ..., J. Greven, Utrecht, 1874; J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat. 1874, 9, 445-454; P. J. Ramberg, G. J. Somsen, Ann. Sci. 2001, 58, 51-74 (this article provides a new English translation of the Voorstel and also discusses the proper spelling of van't Hoff's surname);
20. b) H. van't Hoff, Voorstel tot uitbreding der tegenwoordig in de scheikundegebruikte structur-formules in de ruimte: ..., J. Greven, Utrecht, 1874; J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat. 1874, 9, 445-454; P. J. Ramberg, G. J. Somsen, Ann. Sci. 2001, 58, 51-74 (this article provides a new English translation of the Voorstel and also discusses the proper spelling of van't Hoff's surname);
21. c) P. J. Ramberg, Chemical Structure, Spatial Arrangement: The Early History of Stereochemistry, 1874-1914, Ashgate, Aldershot, UK, 2003. This work appeared just as this article was submitted.
22. a) A. Sementsov, Am. Sci. 1955, 43, 97-100;
23. b) H. A. M. Snelders in van't Hoff-Le Bel Centennial (Ed.: O. B. Ramsey), American Chemical Society, Washington, DC, 1975, pp. 67-72; R. B. Grossman, J. Chem. Educ. 1989, 66, 30-33.
24. b) H. A. M. Snelders in van't Hoff-Le Bel Centennial (Ed.: O. B. Ramsey), American Chemical Society, Washington, DC, 1975, pp. 67-72; R. B. Grossman, J. Chem. Educ. 1989, 66, 30-33.
25. H. Kolbe, J. Prakt. Chem. 1877,15, 473-477.
26. a) W. H. Brock, The Norton History of Chemistry, W. W. Norton, New York, 1993, pp. 262-263;
27. b) A. J. Rocke, The Quiet Revolution: Hermann Kolbe and the Science of Organic Chemistry, University of California Press, Berkeley, 1993.
28. J. H. Brooke, Hist. Stud. Phys. Sci. 1975, 6, 405-429.
29. Ref. [14b], pp. 55-65.
30. V. Meyer, Ber. Dtsch. Chem. Ges. 1890, 23, 567-619.
31. S. J. Weininger in Of Minds and Molecules: New Philosophical Perspectives on Chemistry (Eds.: N. Bhushan, S. Rosenfeld), Oxford University Press, Oxford, 2000, pp. 143-161.
32. M. J. Nye, From Chemical Philosophy to Theoretical Chemistry: Dynamics of Matter and Dynamics of Disciplines, 1800-1950, University of California Press, Berkeley, 1993, p. 112.
33. A. W. Stewart, Stereochemistry, Longmans, Green, London, 1907, p. 1.
34. Ref. [22], p. 314 (emphasis added).
35. P. J. Ramberg, Hist. Stud. Phys. Biol. Sci. 1995, 26, 89-138.
36. A. Eiloart, A Guide to Stereochemistry, Alexander Wilson, New York, 1892, p. 23.
37. For a thorough discussion of "chemical" versus "physical" atomism see A. J. Rocke, Chemical Atomism in the Nine-teenth Century: From Dalton to Cannizzaro, Ohio State University Press, Columbus, 1984.
38. J. Weyer, Angew. Chem. 1974, 86, 604-611; Angew. Chem. Int. Ed. Engl. 1974, 13, 591-598. Weyer attributes that generation's attitude to the influence of Auguste Comte, although more recent scholars have cast some doubt on that conclusion: B. Bensaude-Vincent, Ann. Sci. 1999, 56, 81-94.
39. J. Weyer, Angew. Chem. 1974, 86, 604-611; Angew. Chem. Int. Ed. Engl. 1974, 13, 591-598. Weyer attributes that generation's attitude to the influence of Auguste Comte, although more recent scholars have cast some doubt on that conclusion: B. Bensaude-Vincent, Ann. Sci. 1999, 56, 81-94.
40. J. Weyer, Angew. Chem. 1974, 86, 604-611; Angew. Chem. Int. Ed. Engl. 1974, 13, 591-598. Weyer attributes that generation's attitude to the influence of Auguste Comte, although more recent scholars have cast some doubt on that conclusion: B. Bensaude-Vincent, Ann. Sci. 1999, 56, 81-94.
41. A. J. Rocke in Beyond History of Science: Essays in Honor of Robert E. Schofield (Ed.: E. Garber), Lehigh University Press, Bethlehem, PA, 1990, pp. 137-155.
42. J. Wislicenus, Ber. Dtsch. Chem. Ges. 1888, 21, 581-585; translation: P.J. Ramberg, Bull. Hist. Chem. 1994., 15/ 16, 53.
43. J. Wislicenus, Ber. Dtsch. Chem. Ges. 1888, 21, 581-585; translation: P.J. Ramberg, Bull. Hist. Chem. 1994., 15/ 16, 53.
44. J. H. van't Hoff, Imagination in Science, Springer, Berlin, 1967.
45. L. D. Barron, J. Am. Chem. Soc. 1979, 101, 269-270; R. G. Woolley, Struct. Bonding (Berlin) 1982, 52, 1-35.
46. L. D. Barron, J. Am. Chem. Soc. 1979, 101, 269-270; R. G. Woolley, Struct. Bonding (Berlin) 1982, 52, 1-35.
47. W.-D. Storer, R. Hoffmann, J. Am. Chem. Soc. 1972, 94, 1661-1668.
48. M.-M. Rohmer, M. Bénard, Chem. Soc. Rev. 2001, 30, 340-354.
49. G. Parkin, Chem. Rev. 1993, 93, 887-911.
50. A. V. Butcher, J. Chatt, J. Chem. Soc. A 1970, 2652-2656.
51. L. Manojlovic-Muir, J. Chem. Soc. Chem. Commun. 1971, 147.
52. J. Chatt, L. Manojlovic-Muir, K. W. Muir, J. Chem. Soc. Chem. Commun. 1971, 655-656.
53. K. Wieghardt, G. Backes-Dahmann, B. Nuber, J. Weiss, Angew. Chem. 1985, 97, 773-774; Angew. Chem. Int. Ed. Engl. 1985, 24, 777-778.
54. K. Wieghardt, G. Backes-Dahmann, B. Nuber, J. Weiss, Angew. Chem. 1985, 97, 773-774; Angew. Chem. Int. Ed. Engl. 1985, 24, 777-778.
55. Y. Jean, A. Lledos, J. K. Burdett, R. Hoffmann, J. Am. Chem. Soc. 1988, 110, 4506-4516.
56. Y. Jean, A. Lledos, J. K. Burdett, R. Hoffmann, J. Chem. Soc. Chem. Commun. 19811, 140-142.
57. W. A. Nugent, J. M. Mayer, Metal-Ligand Multiple Bonds, Wiley, New York, 1988, p. 152.
58. K. Yoon, G. Parkin, A. L. Rheingold, J. Am. Chem. Soc. 1991, 113, 1437-1438.
59. P. J. Desrochers, K.W. Nebesny, M.J. LaBarre, S. E. Lincoln, T. M. Loehr, J.H. Enemark, J. Am Chem. Soc. 1991, 113, 9193-9200.
60. P. J. Desrochers, K. W. Nebesny, M. J. LaBarre, M. A. Bruck, G. F. Neilson, R. P. Sperline, J. H. Enemark, G. Backes, K. Wieghardt, Inorg. Chem. 1994, 33, 15-24.
61. J. Song, M. B. Hall, Inorg. Chem. 1991, 30, 4433-4437.
62. R. Baum, Chem. Eng. News 1991, 69(9), 20.
63. I. Amato, Science 1991, 254, 1452-1453.
64. J. M. Mayer, Angew. Chem. 1992, 104, 293; Angew. Chem. Int. Ed. Engl. 1992, 31, 286.
65. J. M. Mayer, Angew. Chem. 1992, 104, 293; Angew. Chem. Int. Ed. Engl. 1992, 31, 286.
66. J. K. M. Sanders, E. C. Constable, B. K. Hunter, C. M. Pearce, Modern NMR Spectroscopy: A Workbook of Chemical Problems, Oxford University Press, New York, 1993, p. 1-6.
67. J. A. Labinger, C. R. Chim. 2002, 5, 235-244. The section presented here was adapted from this article.
68. A. P. Bashall, S. W. A. Bligh, A. J. Edwards, V. C. Gibson, M. McPartlin, O. B. Robinson, Angew. Chem. 1992, 104, 1664-1666; Angew. Chem. Int. Ed. Engl. 1992, 31, 1607-1609.
69. A. P. Bashall, S. W. A. Bligh, A. J. Edwards, V. C. Gibson, M. McPartlin, O. B. Robinson, Angew. Chem. 1992, 104, 1664-1666; Angew. Chem. Int. Ed. Engl. 1992, 31, 1607-1609.
70. A. Bashall, V. C. Gibson, T. P. Kee, M. McPartlin, O. B. Robinson, A. Shaw, Angew. Chem. 1991, 103, 1021-1023; Angew. Chem. Int. Ed. Engl. 1991, 30, 980-982.
71. A. Bashall, V. C. Gibson, T. P. Kee, M. McPartlin, O. B. Robinson, A. Shaw, Angew. Chem. 1991, 103, 1021-1023; Angew. Chem. Int. Ed. Engl. 1991, 30, 980-982.
72. V. C. Gibson, M. McPartlin, J. Chem. Soc. Dalton Trans. 1992, 947-956.