From chiral counterions to twisted membranes

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13486-13494

  Berthier, Damien ^a   Buffeteau, Thierry ^b   Léger, Jean Michel ^c   Oda, Reiko ^a   Huc, Ivan ^a  

^a INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

^b Laboratoire de Physico Chimie Moleculaire   (France)

^c Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MEMBRANES; MICROMETERS; NUCLEAR MAGNETIC RESONANCE; POSITIVE IONS; X RAY DIFFRACTION;

AMPHILILE;

ORGANIC COMPOUNDS;

ANION; CATION; ION; TARTARIC ACID;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; MEMBRANE; VIBRATION; X RAY DIFFRACTION;

EID: 0037073168     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027660j     Document Type: Article

References (88)

1. (a) Yager, P.; Schoen, P. E. Mol. Cryst. Liq. Cryst. 1984, 106, 371-381.
2. (b) Nakashima, N.; Asakuma, S.; Kim, J.-M.; Kunitake, T. Chem. Lett. 1984, 1709-1712.
3. (c) Yamada, K.; Ihara, H.; Ide, T.; Fukumoto, T.: Hirayama, C. Chem. Lett. 1984, 1713-1716.
4. (d) Fuhrhop, J.-H.; Schnieder, P.; Boekema, E.; Helfrich. W. J. Am. Chem. Soc. 1988, 110, 2861-2867.
5. (e) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570.
6. (f) Chung, D. S.; Benedek, G. B.; Konikoff, F. M.: Donovan, J. M. Proc. Natl. Acad. Sci. U.S.A, 1993, 90, 11341-11345.
7. (g) Kulkarni, V. S.: Anderson, W. H.; Brown, R. E. Biophys. J. 1995, 69, 1976-1986.
8. (h) Giuleri, F.; Guillod, F.; Greiner, J.; Krafft, M.-P.; Riess, J. G. Chem. - Eur. J. 1996, 2, 1335-1339.
9. (i) Ringler, P.; Müller, W.; Ringsdorf, H.; Brisson, A. Chem. - Eur. J. 1997, 3, 620-625.
10. (j) Cornelissen, J. J. L. M.; Fisher, M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427-1430.
11. (k) Sommerdijk, N. A. J. M.; Buynters, P. J. J. A.; Akdemir, H.: Geurts, D. G.; Pistorius, A. M. A.; Feiters, M. C.; Nolte, R. J. M.; Zwanenburg, B. Chem. - Eur. J. 1998, 4, 127-136.
12. (l) Nakasawa, I.; Masuda, M.; Okada, Y.; Hanada, T.; Yase, K.; Asai, M.; Shimizu, T. Langmuir 1998, 15, 4757-4764.
13. (m) Song, J.; Cheng, Q.; Kopta, S.; Stevens, R. C. J. Am. Chem. Soc. 2001, 123, 3205-3213.
14. (a) Fuhrhop, J.-H.: Helfrich, W. Chem. Rev. 1993, 93, 1565-1582.
15. (b) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68.
16. When nonchiral amphiphiles assemble into twisted or helical membranes or into tubulues, there is no control over the handedness. See: Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 8871-8875. Lindsell, W. E.; Preston, P. N.; Seddon, J. M.; Rosair, G. M.; Woodman, T. A. J. Chem. Mater. 2000, 12, 1572-1576. Singh, A.; Choen. P. E.: Schnur, J. M. J. Chem. Soc., Chem. Commun, 1988, 1222. Giuleri, F.; Krafft, M.-P.; Riess, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1514-1515. Giuleri, F.; Guillod, F.; Greiner, J.; Krafft. M.-P.; Riess, J. G. Chem. - Eur. J. 1995, 2, 1335.
17. When nonchiral amphiphiles assemble into twisted or helical membranes or into tubulues, there is no control over the handedness. See: Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 8871-8875. Lindsell, W. E.; Preston, P. N.; Seddon, J. M.; Rosair, G. M.; Woodman, T. A. J. Chem. Mater. 2000, 12, 1572-1576. Singh, A.; Choen. P. E.: Schnur, J. M. J. Chem. Soc., Chem. Commun, 1988, 1222. Giuleri, F.; Krafft, M.-P.; Riess, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1514-1515. Giuleri, F.; Guillod, F.; Greiner, J.; Krafft. M.-P.; Riess, J. G. Chem. - Eur. J. 1995, 2, 1335.
18. When nonchiral amphiphiles assemble into twisted or helical membranes or into tubulues, there is no control over the handedness. See: Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 8871-8875. Lindsell, W. E.; Preston, P. N.; Seddon, J. M.; Rosair, G. M.; Woodman, T. A. J. Chem. Mater. 2000, 12, 1572-1576. Singh, A.; Choen. P. E.: Schnur, J. M. J. Chem. Soc., Chem. Commun, 1988, 1222. Giuleri, F.; Krafft, M.-P.; Riess, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1514-1515. Giuleri, F.; Guillod, F.; Greiner, J.; Krafft. M.-P.; Riess, J. G. Chem. - Eur. J. 1995, 2, 1335.
19. When nonchiral amphiphiles assemble into twisted or helical membranes or into tubulues, there is no control over the handedness. See: Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 8871-8875. Lindsell, W. E.; Preston, P. N.; Seddon, J. M.; Rosair, G. M.; Woodman, T. A. J. Chem. Mater. 2000, 12, 1572-1576. Singh, A.; Choen. P. E.: Schnur, J. M. J. Chem. Soc., Chem. Commun, 1988, 1222. Giuleri, F.; Krafft, M.-P.; Riess, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1514-1515. Giuleri, F.; Guillod, F.; Greiner, J.; Krafft. M.-P.; Riess, J. G. Chem. - Eur. J. 1995, 2, 1335.
20. When nonchiral amphiphiles assemble into twisted or helical membranes or into tubulues, there is no control over the handedness. See: Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 8871-8875. Lindsell, W. E.; Preston, P. N.; Seddon, J. M.; Rosair, G. M.; Woodman, T. A. J. Chem. Mater. 2000, 12, 1572-1576. Singh, A.; Choen. P. E.: Schnur, J. M. J. Chem. Soc., Chem. Commun, 1988, 1222. Giuleri, F.; Krafft, M.-P.; Riess, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1514-1515. Giuleri, F.; Guillod, F.; Greiner, J.; Krafft. M.-P.; Riess, J. G. Chem. - Eur. J. 1995, 2, 1335.
21. We found one case of a chiral amphiphile that does not exert control over the screw sense of the helical membrane it forms. See: Thomas, B. N.; Corcoran, R. C.; Cotant, C. L.; Lindemann, C. M.; Kirsch, J. E.; Persichini, P. J. J. Am. Chem. Soc. 1998, 120, 12178-12186. Thomas, B. N.; Lindemann, C. M.; Clark, N. A. Phys. Rev. E 1999, 59, 3040-3047.
22. We found one case of a chiral amphiphile that does not exert control over the screw sense of the helical membrane it forms. See: Thomas, B. N.; Corcoran, R. C.; Cotant, C. L.; Lindemann, C. M.; Kirsch, J. E.; Persichini, P. J. J. Am. Chem. Soc. 1998, 120, 12178-12186. Thomas, B. N.; Lindemann, C. M.; Clark, N. A. Phys. Rev. E 1999, 59, 3040-3047.
23. Wilson-Kubalek, E. M.; Brown, R. E.; Celia, H.; Milligan, R. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 8040-8045.
24. Schnur, J. M. Science 1993, 262, 1669-1676.
25. D. E.; Zubarev. E. R.; Stupp, S. I. Angew. Chem., Int. Ed. 2002, 41, 1706. Sugiyasu, K.; Tamaru, S.-I.; Takeuchi, M.; Berthier, D.: Huc, I.; Oda, R.; Shinkai, S. Chem. Commun. 2002, 1212.
26. D. E.; Zubarev. E. R.; Stupp, S. I. Angew. Chem., Int. Ed. 2002, 41, 1706. Sugiyasu, K.; Tamaru, S.-I.; Takeuchi, M.; Berthier, D.: Huc, I.; Oda, R.; Shinkai, S. Chem. Commun. 2002, 1212.
27. Selinger, J. V.; Spector, M. S.; Schnur, J. M. J. Phys. Chem. B 2001, 7157-7169.
28. Nandi, N.: Bagchi, B. J. Am. Chem. Soc. 1996, 118, 11208-16. Nandi, N.; Bagchi, B. J. Phys. Chem. A 1997, 101, 1343-1351.
29. Nandi, N.: Bagchi, B. J. Am. Chem. Soc. 1996, 118, 11208-16. Nandi, N.; Bagchi, B. J. Phys. Chem. A 1997, 101, 1343-1351.
30. Diacetylenic lipids have been the most studied so far. See: Schnur, J. M.; Ratna, B. R.; Selinger, J. V.; Singh, A.; Jyothi, G.; Easwaran, K. R. K. Science 1994, 264, 945-947. Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. Spector, M. S.; Easwaran, K. R. K.; Jyothi, G.; Selinger, J. V.; Singh, A.; Schnur. J. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12943-12946. Spector, M. S.; Selinger, J. V.; Schnur, J. M. J. Am. Chem. Soc. 1997, 119, 8533-8539.
31. Diacetylenic lipids have been the most studied so far. See: Schnur, J. M.; Ratna, B. R.; Selinger, J. V.; Singh, A.; Jyothi, G.; Easwaran, K. R. K. Science 1994, 264, 945-947. Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. Spector, M. S.; Easwaran, K. R. K.; Jyothi, G.; Selinger, J. V.; Singh, A.; Schnur. J. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12943-12946. Spector, M. S.; Selinger, J. V.; Schnur, J. M. J. Am. Chem. Soc. 1997, 119, 8533-8539.
32. Diacetylenic lipids have been the most studied so far. See: Schnur, J. M.; Ratna, B. R.; Selinger, J. V.; Singh, A.; Jyothi, G.; Easwaran, K. R. K. Science 1994, 264, 945-947. Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. Spector, M. S.; Easwaran, K. R. K.; Jyothi, G.; Selinger, J. V.; Singh, A.; Schnur. J. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12943-12946. Spector, M. S.; Selinger, J. V.; Schnur, J. M. J. Am. Chem. Soc. 1997, 119, 8533-8539.
33. Diacetylenic lipids have been the most studied so far. See: Schnur, J. M.; Ratna, B. R.; Selinger, J. V.; Singh, A.; Jyothi, G.; Easwaran, K. R. K. Science 1994, 264, 945-947. Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. Spector, M. S.; Easwaran, K. R. K.; Jyothi, G.; Selinger, J. V.; Singh, A.; Schnur. J. M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12943-12946. Spector, M. S.; Selinger, J. V.; Schnur, J. M. J. Am. Chem. Soc. 1997, 119, 8533-8539.
34. Fuhrhop, J.-H.; Svenson, S.; Boettcher, C.; Rössler, E.; Vieth, H.-M. J. Am. Chem. Soc. 1990, 112, 4307-4312. Svenson, S.; Kirste, B.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1994, 116, 11969-11975. Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
35. Fuhrhop, J.-H.; Svenson, S.; Boettcher, C.; Rössler, E.; Vieth, H.-M. J. Am. Chem. Soc. 1990, 112, 4307-4312. Svenson, S.; Kirste, B.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1994, 116, 11969-11975.Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
36. Fuhrhop, J.-H.; Svenson, S.; Boettcher, C.; Rössler, E.; Vieth, H.-M. J. Am. Chem. Soc. 1990, 112, 4307-4312. Svenson, S.; Kirste, B.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1994, 116, 11969-11975. Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
37. (a) Zana, R.; Benrraou, M.; Rueff, R. Langmuir 1991, 7, 1072.
38. (b) Zana, R.; Talmon, Y. Nature 1993, 362, 228-230.
39. (c) Oda, R.; Panizza, P.; Schmutz, M.; Lequeux, F. Langmuir 1997, 13, 6407.
40. (d) Bühler, E.; Mendes, E.; Boltenhagen, P.; Munch, J. P.; Zana, R.; Candau, S. J. Langmuir 1997, 13, 3096.
41. (e) Oda, R.; Huc, I.; Candau, S. J. Chem. Commun. 1997, 2105-2106.
42. (f) Bhattacharya, S.; De, S.; Langmuir 1999, 15, 3400-3401.
43. (g) Oda, R.; Huc, I.; Homo, J.-C.; Heinrich, B.; Schmutz, M.; Candau, S. J. Langmuir 1999, 15, 2384-2390.
44. (h) Huc, I.; Oda, R. Chem. Commun. 1999, 2025-2026.
45. (i) Bernheim-Groswasser, A.; Zana, R.; Talmon, Y. J. Phys. Chem. B 2000, 17, 4005.
46. (j) Oda, R.; Huc, I.; Danino, D.; Talmon, Y. Langmuir 2000, 16, 9759-9769.
47. Oda, R.; Huc, I.; Candau, S. J. Angew. Chem., Int. Ed. 1998, 37, 2689-2691.
48. Oda, R.; Huc, I.; Schmutz, M.; Candau, S. J.; MacKintosh, F. C. Nature 1999, 399, 566-569.
49. The questions of whether the bilayers are fluid or solidlike and how does their rigidity relate to the observed twisted (saddlelike) and helical (cylindrical) shapes will be the object of a full report.
50. Spector, M. S.; Selinger, J.; Singh, A.; Rodriguez, J. M.; Price, R. R.; Schnur, J. M. Langmuir 1998, 14, 3493-3500.
51. Fuhrhop, J.-H.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 1768-1776.
52. Singh, A.; Burke, T. G.; Calvert, J. M.; Georger, J. H.; Herendeen, B.; Price, R. R.; Schoen, P. E.; Yager, P. Chem. Phys. Lipids 1988, 135-148.
53. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
54. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
55. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
56. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
57. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
58. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
59. For polyacetylenes, see: Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597; Yashima, E.; Madea, K.; Okamoto, Y. Nature 1999, 399, 449-451. For polyisocyanates, see: Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926. For polyguanidines, see: Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197. For polyphosphazene, see: Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122. 7813. For polyisocyanides, see: Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458. For polyanilines, see: Egan, V.; Bernstein, R.; Hohmann, L.; Tran, T.: Kaner, R. B. Chem. Commun. 2001, 801-802 and references therein.
60. Trigger, O.; Sowade, S.; Böttcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1997, 119, 9120-9124.
61. Gawronski, J.; Gawronska, K.; Rychlewska, U. Tetrahedron Lett. 1989, 44, 6071-6074 and references therein.
62. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
63. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
64. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
65. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
66. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
67. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
68. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
69. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
70. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
71. Fair, C. K.; Schlemper, E. O. Acta Crystallogr., Sect. B 1977, 33, 1337. Palmer, R. A.; Ladd, M. F. C. J. Cryst. Mol. Struct. 1977, 7, 123. Perez, S. Acta Crystallogr., Sect. B 1976, 32, 2064. Perez, S. Acta Crystallogr., Sect. B 1977, 33, 1083. Aakeroy, C. B.; Bahra, G. S.; Nieuwenhuyzen, M. Acta Crystallogr., Sect. C 1996, 52, 1471. Abdou, M.; Kratky, C.; Uray, G. Monatsh. Chem. 1990, 121, 1039. Rychlewska, U. J. Mol. Struct. 1999, 474, 235. Aakeroy, C. B.; Hitchcock, P. B.; Seddon, K. R. Chem. Commun. 1992, 553. Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630. Gunes, B.; Soylu, H.; Akkurt, M.; Ozbey, S. Acta Crystallogr., Sect. C 1995, 51, 2346.
72. 1/n space group as a dihydrate. See: Hattori, N.; Masuda, H.; Okabayashi, H.; O'Connor, C. J. J. Mol. Struct. 1998, 13.
73. A full repport of the synthesis, aggregation properties, and polymerization of this compound is in preparation.
74. Okuyama, K.; Soboi, Y.; Iijima, N.; Hirabayashi, K.; Kunitake, T.; Kajiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 1485.
75. Morishita, H.; Ishioka, T., Kobayashi, M.; Sato, K. J. Phys. Chem. 1987, 91, 2273-2278. Amelinckx, S. Acta Crystallogr. 1956, 9, 217-224.
76. Morishita, H.; Ishioka, T., Kobayashi, M.; Sato, K. J. Phys. Chem. 1987, 91, 2273-2278. Amelinckx, S. Acta Crystallogr. 1956, 9, 217-224.
77. 1H NMR signals. See ref 13.
78. For a complete assignment of the IR spectrum of sodium tartrate, see: Kaneko, N.; Kaneko, M.; Takahashi, H. Spectrochim. Acta, Part A 1984, 40A, 33.
79. For studies of the conformations of tartrate esters and tartaric acid based on the VCD spectra of the OH-stretching vibration, see: Polavaparu, P. L.; Ewig, C. S.; Chandramouly. T. J. Am. Chem. Soc. 1987, 109, 7382. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511. Marcott, C.; Blackburn, C. C.; Faulkner, T. R.: Moscowitz, A.; Overend, J. J. Am. Chem. Soc. 1978, 100, 5262. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061. Sugeta, H.; Marcott, C.; Faulkner. T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397.
80. For studies of the conformations of tartrate esters and tartaric acid based on the VCD spectra of the OH-stretching vibration, see: Polavaparu, P. L.; Ewig, C. S.; Chandramouly. T. J. Am. Chem. Soc. 1987, 109, 7382. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511. Marcott, C.; Blackburn, C. C.; Faulkner, T. R.: Moscowitz, A.; Overend, J. J. Am. Chem. Soc. 1978, 100, 5262. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061. Sugeta, H.; Marcott, C.; Faulkner. T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397.
81. For studies of the conformations of tartrate esters and tartaric acid based on the VCD spectra of the OH-stretching vibration, see: Polavaparu, P. L.; Ewig, C. S.; Chandramouly. T. J. Am. Chem. Soc. 1987, 109, 7382. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511. Marcott, C.; Blackburn, C. C.; Faulkner, T. R.: Moscowitz, A.; Overend, J. J. Am. Chem. Soc. 1978, 100, 5262. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061. Sugeta, H.; Marcott, C.; Faulkner. T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397.
82. For studies of the conformations of tartrate esters and tartaric acid based on the VCD spectra of the OH-stretching vibration, see: Polavaparu, P. L.; Ewig, C. S.; Chandramouly. T. J. Am. Chem. Soc. 1987, 109, 7382. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511. Marcott, C.; Blackburn, C. C.; Faulkner, T. R.: Moscowitz, A.; Overend, J. J. Am. Chem. Soc. 1978, 100, 5262. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061. Sugeta, H.; Marcott, C.; Faulkner. T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397.
83. For studies of the conformations of tartrate esters and tartaric acid based on the VCD spectra of the OH-stretching vibration, see: Polavaparu, P. L.; Ewig, C. S.; Chandramouly. T. J. Am. Chem. Soc. 1987, 109, 7382. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511. Marcott, C.; Blackburn, C. C.; Faulkner, T. R.: Moscowitz, A.; Overend, J. J. Am. Chem. Soc. 1978, 100, 5262. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061. Sugeta, H.; Marcott, C.; Faulkner. T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397.
84. Holzwarth, G.; Chabay, I. J. Chem. Phys. 1972, 57, 1632.
85. Tinoco, I. Radiat. Res. 1963, 20, 133.
86. Using ab initio quantum mechanic calculations, the signs and intensities of the VCD bands may in principle be interpreted to give a precise description of the conformation. But, this goes beyond the scope of this work and will be explored in the sequel.
87. Ardhammar, M.; Nordén. B.; Kurucsev, T. In Circular Dichroism: Principles and Applications, Second Edition; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH Inc.: New York, 2000; pp 741-768.
88. Green, M. M.: Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger. R. L. B.; Selinger, J. V. Angew. Chem. Int. Ed. 1999, 38, 3138-3154.