Systematic Analysis of Structural Data as a Research Technique in Organic Chemistry

Accounts of Chemical Research

Volumn 16, Issue 5, 1983, Pages 146-153

  Allen, Frank H ^a   Kennard, Olga ^a   Taylor, Robin ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 11644328584     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00089a001     Document Type: Article

References (55)

1. This Account complements an earlier paper that was primarily concerned with the chemical interpretation of individual structures: Wilson, S. R.; Huffman, J. C. J. Org. Chem. 1980, 45, 560–566.
2. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. Acta Crystallogr. Sect. B 1979, B35, 2331–2339 and references therein.
3. Bibliographic information is also published annually in: “Molecular Structures and Dimensions”, Kennard, O., Watson, D. G., Allen, F. H., Bellard, S., Eds.; D. Reidel: Dordrecht, The Netherlands.
4. Sutton, L. E., Ed., “Tables of Interatomic Distances and Configuration in Molecules and Ions”; The Chemical Society: London; Special Publication 11 (1958) and 18 (1965).
5. Arnott, S.; Hukins, D. W. L. Biochem. J. 1972, 130, 453–465.
6. Arnott, S.; Scott, W. E. J. Chem. Soc., Perkin Trans. II 1972, 324–335.
7. Taylor, R.; Kennard, O. J. Mol. Struct. 1982, 78, 1–28.
8. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 3209–3212.
9. Domenicano, A.; Vaciago, A.; Coulson, C. A. Acta Crystallogr., Sect. B 1975, B31, 221–234.
10. Domenicano, A.; Vaciago, A.; Coulson, A. A. Acta Crystallogr., Sect. B 1975, B31, 1630–1641.
11. Domenicano, A.; Mazzeo, P.; Vaciago, A. Tetrahedron Lett. 1976, 1029–1032.
12. Domenicano, A.; Vaciago, A. Acta Crystallogr., Sect. B 1979, B35, 1382–1388.
13. Domenicano, A.; Murray-Rust, P. Tetrahedron Lett. 1979, 2283–2286.
14. A similar independent analysis is described by: Norrestam, R.; Schepper, L. Acta Chem. Scand. Sec. A 1981, A35, 91–103. The two sets of angle deformations have a correlation coefficient of 0.966 and a root mean square deviation of 0.22°.
15. Ehrenson, S.; Brownlee, R. T. C.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1–80.
16. Charten, M. “The Chemistry of Alkenes”; Zabicky, J., Ed.; Interscience, London, 1970; Vol. II, pp 511–610.
17. Pete, J.-P. Bull. Soc. Chim. Fr. 1967, 357–370.
18. Hoffmann, R. J. Chem. Phys. 1964, 40, 2480–2488.
19. Hoffmann R.; Stohrer, W.-D. J. Am. Chem. Soc. 1971, 93, 6941–6948.
20. Hoffmann, R. Tetrahedron Lett. 1970, 2907–2909.
21. Hoffmann, R.; Davidson, R. B. J. Am. Chem. Soc. 1971, 93, 5699–5705.
22. Allen, F. H. Acta Crystallogr., Sect. B 1980, B36, 81–96.
23. Allen, F. H. In “Molecular Structure and Biological Activity”; Griffin, J. F., Duax, W. L., Eds.; Elsevier Biomedical: New York, 1982; 105–116.
24. Allen, F. H. Acta Crystallogr., Sect. B 1981, B37, 890–900.
25. Bernett, W. A. J. Chem. Educ. 1967, 44, 17–24 and references therein.
26. Altona, C.; Geise, H. J.; Romers, C. Tetrahedron 1968, 24, 13–32.
27. Duax, W. L.; Norton, D. A. “Atlas of Steroid Structures”; Plenum: London, 1975.
28. Duax, W. L.; Weeks, C. M.; Rohrer, D. C. Recent Prog. Horm. Res. 1976, 32, 81–116.
29. Mathieson, A.McL. Perspect. Struct. Chem. 1967, 1, 41–108.
30. Dunitz, J. D. Perspect. Struct. Chem. 1968, 2, 1–70.
31. The correlation of crystal structure conformations with pharmaceutical activity cannot be covered adequately here. Interested readers are referred to: Griffin, J. F.; Duax, W. L., Eds., “Molecular Structure and Biological Activity”; Elsevier Biomedical: New York, 1982.
32. Barton, D. H. R.; Head, A. J.; May, P. J. J. Chem. Soc. 1957, 935–944.
33. Barton, D. H. R.; McCapra, F.; May, P. J.; Thudium, F. J. Chem. Soc. 1960, 1297–1311.
34. Guy, J. J.; Allen, F. H.; Kennard, O.; Sheldrick, G. M. Acta Crystallogr., Sect. B 1977, B33, 1236–1244.
35. Courseille, C.; Precigoux, G.; Leroy, F.; Busetta, B. Cryst. Struct. Commun. 1973, 2, 441–446.
36. Ceccarelli, C.; Jeffrey, G. A.; Taylor, R. J. Mol. Struct. 1981, 70, 255–271.
37. Newton, M. D.; Jeffrey, G. A.; Takagi, S. J. Am. Chem. Soc. 1979, 101 1997–2002.
38. Taylor, R. J. Mol. Struct. 1981, 73, 125–136.
39. For example, Diercksen, G. H. F. Theor. Chim. Acta 1971, 21, 335–367.
40. Olovsson, I.; Jönsson, P.-G. In “The Hydrogen Bond—Recent Developments in Theory and Experiments”; Schuster, P., Zundel, G., Sandorfy, C., Eds.; Elsevier North-Holland: Amsterdam, 1976; Vol 2 416–420.
41. Del Bene, J. E.; Pople, J. A. J. Chem. Phys. 1973, 58, 3605–3608.
42. Jeffrey, G. A.; Lewis, L. Carbohydr. Res. 1978, 60, 179–182.
43. Jeffrey, G. A.; Takagi, S. Acc. Chem. Res. 1978, 11, 264–270.
44. Jeffrey, G. A.; Maluszynska, H. Int. J. Biol. Macromol. 1982, 4, 173–185.
45. Taylor, R.; Kennard, O. J. Am. Chem. Soc., 1982, 104, 5063–5070.
46. Bondi, A. J. Phys. Chem. 1964, 68, 441–451.
47. Kitaigorodsky, A. I. “Molecular Crystals and Molecules”; Academic Press: New York and London, 1973; 10–18.
48. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065–5067.
49. Dunitz, J. D. “X-Ray Analysis and the Structure of Organic Molecules”; Cornell University Press: Ithaca and London, 1979; 366–379.
50. Kaftory, M.; Dunitz, J. D. Acta Crystallogr., Sect. B 1975, B31, 2912–2914.
51. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. Acta Crystallogr., Sect. B 1974, B30, 1517–1527.
52. Rosenfield, R. E.; Parthasarathy, R.; Dunitz, J. D. J. Am. Chem. Soc. 1977, 99, 4860–4862.
53. For other reaction pathway studies, see: Bürgi, H. B. Inorg. Chem. 1973, 12, 2321–2325.
54. Bürgi, H. B. Angew. Chem., Int. Ed. Engl. 1975, 14, 460–473.
55. Britton, D.; Dunitz, J. D. Helv. Chim. Acta 1980, 63, 1068–1073.