A Link Between Macroscopic Phenomena and Molecular Chirality: Crystals as Probes for the Direct Assignment of Absolute Configuration of Chiral Molecules

Topics in Stereochemistry

Volumn 16, Issue , 2007, Pages 1-85

  Addadi, L ^a   Berkovitch Yellin, Z ^a   Weissbuch, I ^a   Lahav, M ^a   Leiserowitz, L ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Bijvoet method; Crystal dissolution; Crystal growth; Glycylglycine; Pasteur type resolution

Indexed keywords

CRYSTAL GROWTH;

ASSIGNMENT OF ABSOLUTE CONFIGURATION; BIJVOET METHOD; CHIRAL MOLECULE; CRYSTAL DISSOLUTION; GLYCYL-GLYCINE; MACROSCOPIC PHENOMENA; MOLECULAR CHIRALITY;

STEREOCHEMISTRY;

EID: 85048374807     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470147252.ch1     Document Type: Chapter

References (132)

1. Pasteur, L. Ann. Phys. 1848, 24, 442.
2. Van't Hoff, J. H. Arch. Neerl. Sci. Exactes. Nat. 1874, 9, 445.
3. Le Bel, J. A. Bull. Soc. Chim. France 1874, 22, 337.
4. Fischer, E. Chem. Ber. 1891, 24, 2683.
5. Rosanoff, M. A. J. Am. Chem. Soc. 1906, 28, 114.
6. Bijvoet, J. M.; Peerdeman, A. F.; Van Bommel, J. A. Nature 1951, 168, 271.
7. Kirkwood, J. G.; Wood, W. W.; Fickett, W. J. Chem. Phys. 1952, 20, 561.
8. Dunitz, J. D. "X-Ray Analysis and the Structure of Organic Molecules" Cornell University Press: Ithaca, New York, 1979, p. 129.
9. "Perhaps looking-glass milk isn't good to drink," wondered Alice in " Through the Looking Glass" by Lewis Carroll.
10. Groth, P. "Chemische Kristallographie," Bd. 1-5; Verlag von Wilhelm Engelmann: Liepzig, 1919.
11. Dunitz, J.D. in G. M. J. Schmidt et al. "Solid State Photochemistry" D. Ginsburg, Ed.; Verlag Chemie: Weinheim, 1976, p. 261.
12. Mason, S. F. "Molecular Optical Activity and Chiral Discrimination" Cambridge University Press: Cambridge, England, 1980.
13. In ref. 8, pp. 1-72.
14. Nishikawa, S.; Matsukawa, R. Proc. Imp. Acad. Japan 1928, 4, 96.
15. Coster, D.; Knol, K. S.; Prins, J. A. Z. Phys. 1930, 63, 345.
16. Bijvoet, J. M. Proc. Koninkl. Ned. Akad. Wetenschap. 1949, B52, 313.
17. Trommel, J.; Bijvoet, J. M. Acta Crystallogr. 1954, 7, 703.
18. Hope, H.; de la Camp, U. Acta Crystallogr. 1972, A28, 201.
19. Rabinovich, D.; Hope, H. Acta Crystallogr. 1975, A31, S128.
20. Green, B. S.; Rabinovich, D.; Shakked, Z.; Hope, H.; Swanson, K. Acta Crystallogr. 1981, B37, 376.
21. "International Tables for X-Ray Crystallography." Vol. IV; The Kynoch Press: Birmingham, England, 1974.
22. Stehn, J. R.; Goldberg, M. D.; Mayumo, B. A.; Wiener-Chasman, R. "Neutron Cross Section" (BNL 325); Brookhaven National Laboratory: 1964.
23. Johnson, C. K.; Gale, J.; Taylor, M. R. L.; Rose, I. A. J. Am. Chem. Soc. 1964, 87, 1852.
24. Seiler, P.; Martinoni, B.; Dunitz, J. D. Nature 1984, 309, 435.
25. Flook, R. J.; Freeman, H. C; Scudder, L. Acta Crystallogr. 1977, B33, 801.
26. Okaya, Y. In "Crystallographic Computing" Ahmed, F. R., Hall, S. R., Huber, C. P., Eds.; Munksgaard: Copenhagen, 1970, p. 127.
27. Tanaka, J. Acta Crystallogr. 1972, A28, 229.
28. Tanaka, J.; Katayama, C; Ogura, F.; Tatemitsu, H.; Nakagawa, H. Chem. Comm. 1973, 21.
29. Brongersma, H. H.; Mul, P. M. Chem. Phys. Lett. 1973, 19, 217.
30. Waser, J. J. Chem. Phys. 1949, 17, 498.
31. Turner, E. E.; Lonsdale, K. J. Chem. Phys. 1950, 18, 156.
32. Buckley, H. E. "Crystal Growth" Wiley: New York, 1951.
33. Wells, A. F. Phil. Mag. 1946, 37, 180, 217, 605.
34. Kern, R. Bull. Soc. Fr. Miner. Crystallogr. 1953, 76, 391.
35. Hartman, P. In "Physics and Chemistry of the Organic Solid State," Vol. 1; Fox, D.; Labes, M. M.; Weisberger, A., Eds.; Interscience: New York, 1963, p. 369. Idem. Ibid., Vol. 2; p. 873.
36. Dunning, W. J. D.; Albon, N. "Growth and Perfection of Crystals" Doremus, R. H.; Roberts, B. W.; Tumbull, D., Eds.; Wiley: London, 1958, p. 416.
37. Smythe, B. M. Aust. J. Chem. 1967, 20, 1115.
38. Mantovani, G.; Gilli, G.; Fagioli, F. Compi. Rend. XIII Assembly 1967, C115, 289.
39. Van Hook, A. Kristal. Acad. Nauk. SSSR Inst. Kristallogr. 1968, 8, 45.
40. Van Hook, A. J. ASSBT 1981, 21, 130.
41. Michaelis, A. S.; van Kreveld, A. Neth. Milk Dairy J. 1966, 20, 163.
42. Wells, A. F. Disc. Faraday Soc. 1949, 5, 197.
43. Berkovitch-Yellin, Z.; van Mil, J.; Addadi, L.; Idelson, M.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1985, 107, 3111.
44. Addadi, L.; Berkovitch-Yellin, Z.; Weissbuch, I.;van Mil, J.; Shimon, L. J. W.; Lahav, M.; Leiserowitz, L. Angew. Chem. Int. Ed. Engl., 1985, 24, 466.
45. Addadi, L.; Weissbuch, I.; Berkovitch-Yellin, Z.; Lahav, M.; Leiserowitz, L.; Weinstein, S. J. Am. Chem. Soc. 1982, 104, 2075.
46. Addadi, L.; Berkovitch-Yellin, Z.; Domb, N.; Gati, E.; Lahav, M.; Leiserowitz, L. Nature 1982, 296, 21.
47. Weissbuch, I.; Addadi, L.; Berkovitch-Yellin, Z.; Gati, E.; Weinstein, S.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 6615.
48. Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. A 1969, 2372.
49. Wang, J. L. Unpublished results.
50. Leiserowitz, L.; Tuval, M. Acta Crystallogr. 1978, B34, 1230.
51. Berkovitch-Yellin, Z.; Addadi, L.; Idelson, M.; Lahav, M.; Leiserowitz, L. Angew. Chem. Suppl. 1982, 1336.
52. Blake, C. C; Small, R. W. Acta Crystallogr. 1972, B28, 201.
53. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1980, 102, 1611.
54. Addadi, L.; Weinstein, S.; Gati, E.; Weissbuch, I.; Lahav, M. J. Am. Chem. Soc. 1982, 704, 4610.
55. Sequeira, A.; Rajagopal, H.; Chidambaram, R. Acta Crystallogr. 1972, B28, 2514.
56. Verbist, J. J.; Lehman, M. S.; Koetzle, T. F.; Hamilton, W. C. Acta Crystallogr. 1972, B28, 3006.
57. Gil-Av, E.; Hare, P. E.; Tishbee, A. J. Am. Chem. Soc. 1980, 102, 5115.
58. Weinstein, S. Angew. Chem. Int. Ed. Engl. 1982, 21, 218.
59. Fredga, A. Tetrahedron 1960, 8, 126.
60. Honess, A. P. "The Nature, Origin and Interpretation of Etch Figures on Crystals" Wiley: New York, 1927, p. 6.
61. Johnston, W. G. In "Progress in Ceramic Science," Vol. 2; Burke, Z. E., Ed.; Pergamon: Oxford, 1962, p. 175.
62. Franck, F. C. In "Growth and Perfection of Crystals" Doremus, R. H.; Roberts, B. W. Tumbull, D., Eds.; Wiley: New York, 1958, p. 411.
63. Hari Babu, V.; Subba Rao, V. V. Progr. Cryst. Growth Charact. 1984, 8, 261.
64. Thomas, J. M.; Evans, E. L.; Clarke, T. A. J. Chem. Soc. A 1971, 2338.
65. Shimon, L. J. W.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1985, 107, 3375.
66. For a recent review on polar crystals, see Paul, I. C; Curtin, D. Y. Chem. Rev. 1981, 81, 525.
67. Berkovitch-Yellin, Z.; Addadi, L.; Idelson, M.; Leiserowitz, L.; Lahav, M. Nature 1982, 296, 27.
68. Visser, R. A.; Bennema, P. Neth. Milk Dairy J. 1983, 37, 109.
69. Visser, R. A. Ph.D Thesis, Catholic University of Nijmegen, Holland, 1983.
70. Traube, N. N. Jahrb. F. Min. Geol. USW, Beilage Bd. 7, 1891, S430.
71. Fries, P.C.; Rao, S. T.; Sundaralingam, M. Acta Crystallogr. 1971, B27, 994.
72. Beevers, C. A.; Hansen, H. N. Acta Crystallogr. 1971, B27, 1323.
73. Smythe, B. M. Sugar Technol. Rev. 1971, 191.
74. Jeffrey, G. A.; Park, Y. J. Acta Crystallogr. 1972, B28, 257.
75. Berman, H. M. Acta Crystallogr. 1970, B26, 290.
76. Cahn, R. S.; Ingold, C; Prelog, V. Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
77. Prelog, V.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1982, 21, 567.
78. Winter, C. E. J. Chem. Ed. 1983, 60, 550.
79. Weissbuch, I.; Shimon, L. J. W.; Berkovitch-Yellin, Z.; Addadi, L.; Leiserowitz, L.; Lahav, M. Isr. J. Chem. 1985, 25, 353.
80. Weissbuch, I.; Berkovitch-Yellin, Z.; Leiserowitz, L.; Lahav, M. Isr. J. Chem. 1985, 25, 362.
81. Frey, M. N.; Lehman, M. S.; Koetzle, T. F.; Hamilton, W. C. Acta Crystallogr. 1973, B29, 876.
82. The terms "enantiotopic" and "nomotopic" are used according to the nomenclature introduced by K. Mislow and M. Raban, Top. Stereochem. 1967, 1, 1.
83. Ariel, S. Ph.D. Thesis, Feinberg Graduate School, Weizmann Institute of Science, Rehovot, Israel, 1981.
84. Legros, S. P.; Kvick, A. Acta Crystallogr. 1980, B36, 3052, and references therein.
85. Weissbuch, I.; Addadi, L.; Berkovitch-Yellin, Z.; Gati, E.; Lahav, M.; Leiserowitz, L. Nature 1984, 310, 161.
86. Freeman, H. C; Paul, G. L.; Sabine, T. M. Acta Crystallogr. 1970, 526, 925.
87. Cameron, T. S.; Duffin, M. Cryst. Struct. Comm. 1974, 3, 539.
88. Wei, K. T.; Wald, D. L. Acta Crystallogr. 1977, B33, 797.
89. Donohue, J. J. Am. Chem. Soc. 1950, 72, 949.
90. Weissbuch, I.; Shimon, L. J. W.; Wulff, J. Work in progress.
91. Wang, J. L.; Berkovitch-Yellin, Z.; Leiserowitz, L. Acta Crystallogr. 1985, B41, 341.
92. Wang, J. L.; M.Sc. Thesis, Feinberg Graduate School, Weizmann Institute of Science, Rehovot, Israel, 1983.
93. Weisinger, Y.; Frolow, F.; McMullan, R.; Leiserowitz, L. Work in progress.
94. Miller, R. S.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1974, 96, 6340.
95. Duesler, E. N.; Kress, R. B.; Lin, C. T.; Shiau, W. I.; Paul, I. C; Curtin, D. Y. J. Am. Chem. Soc. 1981, 103, 875.
96. Chenchalah, P. C; Holland, H. L.; Richardson, M. F. J. Chem. Soc. Chem. Comm. 1982, 436.
97. Schmidt, G. M. J. J. Chem. Soc. 1964, 2014.
98. Hung, J. D.; Lahav, M.; Luwisch, M.; Schmidt, G. M. J. Isr. J.Chem. 1972, 10, 585.
99. Van Mil, J.; Vaida, M. Work in progress.
100. Hartman, P.; Perdok, W. G. Acta Crystallogr. 1955, 8, 49.
101. Hartman, P. J. Cryst. Growth 1980, 49, 157, 166.
102. Berkovitch-Yellin, Z. J. Am. Chem. Soc. in press.
103. Saska, M.; Myerson, A. S. J. Cryst. Growth 1983, 61, 546.
104. Wireko, F. C; Berkovitch-Yellin, Z.; Frolow, F.; Lahav, M.; Leiserowitz, L. Submitted for publication.
105. Davey, R. J. J. Cryst. Growth 1976, 34, 109.
106. Davey, R. J. In "Current Topics in Material Science," Vol. 8; Kaldis E., Ed.; North Holland: Amsterdam, 1982, Chapter 6.
107. Bourne, S. R. A1CHE Symp. Ser. 1980, 193, 76.
108. Milisavljevic, B. C. Ph.D. Thesis, Swiss Federal Institute of Technology, Zurich, 1982 (Dissertation N6898).
109. Berkovitch-Yellin, Z.; Leiserowitz, L. Acta Crystallogr. 1984, B40, 159.
110. Abrahams, S. C. In "Anomalous Scattering" Ramaseshan, S.; Abrahams, S. C, Eds.; Munksgaard: Copenhagen, 1974, p. 199.
111. Glazer, A. M.; Moxon, J. R. L.; Stadnika, K. M.; Thomas, P. A. In "Collected Abstracts of the 13th International Congress of Crystallography" Bonse, V., Ed.; Hitzegrad: Dortmund, 1984, p. C-150.
112. Fletcher, S. R.; Keve, E. T.; Skapski, A. C. Ferroelectrics 1976, 14, 775, and references therein.
113. Rogers, D. Acta Crystallogr. 1981, A37, 734.
114. Bernardinelli, G.; Flack, H. D. Acta Crystallogr. 1985, A41, 500.
115. Lock, P. J. Appl. Pkys. Lett. 1971, 19, 390.
116. Patil, A. A.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1985, 107, 726.
117. Arigoni, D. Private communication. See also ref. 8, p. 144.
118. Ottensmeyer, F. P. Am. Rev. Blophys. Bioeng. 1979, 8, 129.
119. Korn, A. P.; Spitnik-Elson, P.; Elson, D. J. Biol. Chem. 1982, 257, 7155.
120. Unwin, P. N. T.; Henderson, R. Sc. Am. 1984, 250 (February), 56.
121. Unwin, P. N. T.; Henderson, R. J. Mol. Biol. 1975, 94, 25.
122. Krasnow, M. A.; Stasiak, A.; Spengler, S. J.; Dean, F.; Koller, T.; Cozzarelli, N. R. Nature 1983, 304, 559.
123. Di Capua, E.; Engel, A.; Stasiak, A.; Koller.T. J. Mol. Biol. 1982, 157, 87.
124. Horten, B. W.; Birdsall, D. H. J. Colloid Sei. 1952, 7, 284.
125. Tashibana, T.; Kambara, H. J. Am. Chem. Soc. 1965, 87, 3015.
126. Hidaka, H.; Murata, M.; Onai, T. J. Chem. Soc. Chem. Comm. 1984, 562.
127. Weis, R. M.; McConnel, H. M. Nature 1984, 310, 47.
128. Nakashima, N.; Asakuma, S.; Kunitake, T. J. Am. Chem. Soc. 1985, 107, 509.
129. Fryer, J. R.; Smith, J. R. Proc. Roy. Soc. London 1982, A381, 225.
130. Uyeda, N.; Kobayashi, T.; Ishizuka, K.; Fuyiyoshi, Y. Nature 1980, 285, 96.
131. We thank Prof. J. M. Thomas and Dr. W. Jones for useful discussions on this aspect of electron microscopy.
132. Fryer, J. R.; Hann, R. A.; Eyres, B. L. Nature 1985, 313, 382.