Factors affecting conformation of (R,R)-tartaric acid ester, amide and nitrile derivatives. X-Ray diffraction, circular dichroism, nuclear magnetic resonance and ab initio studies

Tetrahedron

Volumn 53, Issue 17, 1997, Pages 6113-6144

  Gawroński, Jacek ^a   Gawrońska, Krystyna ^a   Skowronek, Pawel ^a   Rychlewska, Urszula ^a   Warzajtis, Beata ^a   Rychlewski, Jacek ^a   Hoffmann, Marcin ^a   Szarecka, Agnieszka ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

TARTARIC ACID DERIVATIVE;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; THEORY; X RAY DIFFRACTION;

EID: 0040550735     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00271-8     Document Type: Article

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21. (+)-Tartaric acid: (a) Stern, F.; Beevers, C. A. Acta Crystallogr. 1950, 3, 341. (b) Okaya, Y.; Stemple, N. R., Kay, M. I. ibid. 1966, 21, 237. (c) Albertsson, J.; Oskarsson, A.; Stahl, K. J. Appl. Crystallogr. 1979, 12, 537.
22. (+)-Tartaric acid: (a) Stern, F.; Beevers, C. A. Acta Crystallogr. 1950, 3, 341. (b) Okaya, Y.; Stemple, N. R., Kay, M. I. ibid. 1966, 21, 237. (c) Albertsson, J.; Oskarsson, A.; Stahl, K. J. Appl. Crystallogr. 1979, 12, 537.
23. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
24. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
25. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
26. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
27. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
28. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
29. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
30. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
31. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
32. Salts of (+)-tartaric acid - examples: (a) Van Bommel, A. J.; Bijvoet, J. M. Acta Cryst. 1958, 11, 61. (b) Buschmann, J.; Luger, P. ibid. 1985, C41, 206. (c) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1982, B38, 2461. (d) Hawthorne, F. C.; Borys, I.; Ferguson, R. B. ibid. 1983, C39, 540. (e) Ortega, R. B.; Campana, C. F.; Tapscott, R. E. ibid. 1980, B26, 1786. (f) Templeton, L. K.; Templeton, D. H.; Zhang, D.; Zalkin, A. ibid. 1985, C41, 363. (g) Templeton, D. H.; Zalkin, A.; Ruben, H. W.; Templeton, L. K. ibid. 1979, B35, 1608. (h) Prout, C. K.; Carruthers, J. R.; Rossotti, F. J. C. J. Chem. Soc. 1971, 3336. (i) Ambady, G. K. Acta Crystallogr. 1968, B24, 1548. (j) Ambady, G. K.; Kartha, G. ibid. 1968, B24, 1540.
33. Salts of (+)-tartaric acid with complex cations - review: Tapscott, R. E.; Belford, R. L., Paul, I. C. Coord. Chem. Rev. 1969, 4, 323.
34. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
35. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
36. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, E38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
37. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
38. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, E38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
39. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
40. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
41. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, E38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
42. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
43. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
44. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
45. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
46. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
47. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
48. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
49. Salts of (+)/(-)-tartaric acid with amines - examples: (a) Molins, E.; Miravitlles, C.; López-Calahorra, F.; Castells, J.; Raventós, J. Acta Crystallogr. 1989, C45, 104. (b) Jensen, B. ibid. 1988, C44, 1602. (c) Ma, L. Y. Y.; Camerman, N. ibid. 1987, C43, 316. (d) Gould, R. O.; Taylor, P.; Walkinshaw, M. D.; Slot, H. J. B. ibid. 1987, C43, 2405. (e) Jensen, B. ibid. 1982, B38, 1185. (f) Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. (g) Fair, C. K.; Schlemper, E. O. Acta Crystallogr. 1977, B33, 1337. (h) Pérez, S. ibid. 1977, B33, 1083. (i) Pérez, S. ibid. 1976, B32, 2064. (j) Ruble, J. R.; Hite, G.; Soares, J. R. ibid. 1976, B32, 136. (k) Jensen, B. Acta Chem. Scand. 1976, B30, 643. (l) Bye, E. ibid. 1975, B29, 22. (m) Hite, G.; Soares, J. R. Acta Cryst. 1973, B29, 2935. (n) Carlström, D. ibid. 1973, B29, 161. (o) Peeters, O.M.; deRanter, C.J.; Blaton, N.M. Acta Crystallogr. 1982, B38, 3055 (p) Kamiya, K.; Takamoto, M.; Wada, Y.; Fujino, M., Nishikawa, M. J.Chem. Soc., Chem. Comm. 1980, 438.
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99. Reported Δε for 1a: -3.8 at 216 nm: Thiemann, W. Tetrahedron, 1971, 27, 1465. For acid solution of (evidently erroneously labelled) D-tartaric acid reported Δε is -4.4 at 216 nm: Katzin, L.I; Gulyas, E. J.Am.Chem.Soc. 1968, 90, 247.
100. 2 (see section B).
101. α stereogenic center is the primarily factor responsible for the generation of the n-π* Cotton effect.
102. Harada, N.; Nakanishi, K. J. Am. Chem. Soc. 1969, 91, 3989.
103. For reviews see: (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books: Mill Valley 1983; (b) Nakanishi, K.; Berova, N. in Circular Dichroism - Principles and Applications, Nakanishi, K.; Berova, N.; Woody, R. W. (eds.), pp. 361-398, Verlag Chemie: New York 1994; (c) Gawronski, J. in Houben-Weyl Methods of Organic Chemistry, 4th ed., vol. E21a, Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (eds.), pp. 509-533, Thieme: Stuttgart 1995.
104. For reviews see: (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books: Mill Valley 1983; (b) Nakanishi, K.; Berova, N. in Circular Dichroism - Principles and Applications, Nakanishi, K.; Berova, N.; Woody, R. W. (eds.), pp. 361-398, Verlag Chemie: New York 1994; (c) Gawronski, J. in Houben-Weyl Methods of Organic Chemistry, 4th ed., vol. E21a, Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (eds.), pp. 509-533, Thieme: Stuttgart 1995.
105. For reviews see: (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books: Mill Valley 1983; (b) Nakanishi, K.; Berova, N. in Circular Dichroism - Principles and Applications, Nakanishi, K.; Berova, N.; Woody, R. W. (eds.), pp. 361-398, Verlag Chemie: New York 1994; (c) Gawronski, J. in Houben-Weyl Methods of Organic Chemistry, 4th ed., vol. E21a, Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (eds.), pp. 509-533, Thieme: Stuttgart 1995.
106. The conformation of the benzoate group is assumed planar, with eclipsed (O=)C-O-C-H bond system. See ref. 53, 54 and Inoue, I.; Yamasaki, N.; Yokoyama, T.; Tai, K. J. Org. Chem. 1992, 57, 1332.
107. The second maximum of the exciton Cotton effect at shorter wavelengths is not observed in a number of cases shown in Table 1, probably as a result of cancelling or overlapping by Cotton effects due to other transitions.
108. - conformers we use -35.0 and +21.8, respectively The former amplitude is the average value for 1b, 6b and 10b (see ref. 59) while the latter is that of 15b.
109. 4: C, 67.50; H, 3.78; N, 8.75; Found: C, 67.21; H, 3.77; N, 8.70.
110. 27b
111. Cyr, N.; Hamer, G. K.; Perlin, A. S. Can. J. Chem. 1978, 56, 297.
112. 3OD), respectively.
113. Duddeck, H. in Houben-Weyl Methods of Organic Chemistry, vol. E21a, Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., (eds.), p. 309, Thieme: Stuttgart 1995.
114. 180° = 10.3 Hz.
115. Because due to solubility problems various solvents were used in the measurement of H NMR spectra of O,O'-dibenzoyl derivatives 1b-15b, comparison of all δ values is less reliable.
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