Chirality-directed self-assembly of supramolecular propellers of dialkyltartrate trimers with hydronium, ammonium and primary aminium ions in CI mass spectra

Journal of Mass Spectrometry

Volumn 32, Issue 10, 1997, Pages 1072-1079

  Winkler, F Johann ^a   Medina, Ramiro ^a   Winkler, Johannes ^a   Krause, Helmut ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Chemical ionization; Chiral recognition; Dialkyltartrates; Proton bound clusters; Supramolecular structures

Indexed keywords

AMINE; AMMONIA; TARTARIC ACID DERIVATIVE; TETRAMER;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; IONIZATION; MASS; MASS SPECTROMETRY; MOLECULAR RECOGNITION; PRIORITY JOURNAL;

EID: 0030717545     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-9888(199711)32:10<1072::AID-JMS561>3.0.CO;2-9     Document Type: Article

References (48)

1. A. G. Harrison, Chemical Ionization Mass Spectrometry, 2nd edn. CRC Press, Boca Raton, FL (1992).
2. F. J. Winkler and J. S. Splitter, in Applications of Mass Spectrometry to Organic Stereochemistry, ed. by J. S. Splitter and F. Turecek, p. 353. VCH, New York (1994).
3. (a) R. D. Smith and K. Light-Wahl, Biol. Mass Spectrom. 22, 493 (1993);
4. (b) D. L. Smith and Z. Zhang, Mass Spectrom. Rev. 13, 411 (1994);
5. (c) M. Vincenti, J. Mass Spectrom. 30, 925 (1995);
6. (d) M. Przybylski and M. O. Glocker, Angew. Chem. Int. Edn Engl. 35, 806 (1996).
7. D. V. Bowen and F. H. Field, Org Mass Spectrom. 9, 195 (1974).
8. F. J. Winkler and F. W. McLafferty, Tetrahedron 30, 2971 (1974).
9. J. O. Metzger, W. Schwarting, P. Köll and F. J. Winkler, Org. Mass Spectrom. 27, 508 (1992).
10. (a) G. Smith and J. A. Leary, J. Am. Chem. Soc. 118, 3293 (1996);
11. (b) G. Smith and J. A. Leary, J. Am. Soc. Mass Spectrom. 7, 953 (1996).
12. M. H. Fales and G. W. Wright, J. Am. Chem. Soc. 99, 2339 (1977).
13. (a) F. J. Winkler, D. Stahl and F. Maquin, Tetrahedron Lett. 27, 335 (1986);
14. (b) F. J. Winkler, J. Winkler and H. Krause, Adv. Mass Spectrom. 11, 620 (1989).
15. E. N. Nikolaev, G. T. Goginashvili, V. L. Tal'rose and R. G. Kostyanosky, Int. J. Mass Spectrom. Ion Process. 86, 249 (1988).
16. F. J. Winkler, R. Medina, J. Winkler and H. Krause, J. Chromatogr.A 666, 549 (1994).
17. (a) G. Hofmeister and J. A. Leary, Org. Mass Spectrom. 26, 811 (1991);
18. (b) T. T. Dang, S. F. Pedersen and J. A. Leary, J. Am. Soc. Mass Spectrom. 5, 452 (1994).
19. (a) M. Sawada, M. Shimuza, Y. Takai, H. Yamada, T. Kaneda and T. Hanafusa, J. Am. Chem. Soc. 114, 4405 (1992);
20. (b) M. Sawada, Y. Takai, H. Yamada, S. Hirayama, T. Kaneda, T. Tanaka, K. Kamada, T. Mizooku, S. Takeuchi, K. Ueno, K. Hirose, Y. Tobe and K. Naemura, J. Am. Chem. Soc. 117, 7726 (1995), and references cited therein.
21. (a) I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc. 115, 4318 (1993);
22. (b) G. Pócsfalvi, M. Lipták, P. Huszthy, J. S. Bradshaw, R. M. Izatt and K. Vékey, Anal. Chem. 68, 792 (1996).
23. J. N. Haskins, M. R. Saunders and P. Camilleri, Rapid Commun. Mass Spectrom. 8, 423 (1994).
24. M. Meot-Ner (Mautner), L. W. Sieck, S. Scheiner and X. Duan, J. Am. Chem. Soc. 116, 7848 (1994).
25. (a) W. J. Herron, M. T. Coolbaugh, G. Vaidyanathan, W. R. Peifer and J. F. Garvey, J.Am. Chem. Soc. 114, 3684 (1992);
26. (b) J. F. Garvey, W. J. Herron and G. Vaidyanathan, Chem. Rev. 94, 1990 (1994);
27. (c) Z. Karpas, G. A. Eiceman, C. S. Harden, R. G. Ewing and P. B. Smith, Org. Mass Spectrom. 29, 159 (1994).
28. M. Dey, F. Moritz, J. Grotemeyer and E. W. Schlag, J. Am. Chem. Soc. 116, 9211 (1994).
29. K. C. Russell, E. Leize, A. Van Dorsselaer and J.-M. Lehn, Angew. Chem. Int. Edn Engl. 34, 209 (1995).
30. X. Cheng, Q. Gao, R. D. Smith, E. E. Simanek, M. Mammen and G. M. Whitesides, Rapid Commun. Mass Spectrom. 9, 312 (1995).
31. G. Hopfgartner, C. Piquet and J. D. Henion, J. Am. Soc. Mass Spectrom. 5, 748 (1994).
32. J. T. Davis, S. Tirumala, J. R. Jenssen, E. Radler and D. Fabris, J. Org. Chem. 60, 4167 (1995).
33. (a) M. Meot-Ner (Mautner), J. Am. Chem. Soc. 105, 4912 (1983);
34. (b) M. Meot-Ner (Mautner), J. Am. Chem. Soc. 106, 278 (1984);
35. (c) M. Meot-Ner (Mautner), J. Am. Chem. Soc. 108, 6189 (1986);
36. (d) R. B. Sharma and P Kebarle, J. Am. Chem. Soc. 106, 3913 (1984);
37. (e) C.-C. Liou, H.-F. Wu and J. S. Brodbelt, J. Am. Soc. Mass Spectrom. 5, 260 (1994).
38. W. Y. Feng, V. Aviyente, T. Varnali and C. Lifshitz, J. Phys. Chem. 99, 1776 (1995).
39. T. Schindler, C. Berg, G. Niedner-Schatteburg and V. E. Bondybey, Chem. Phys. 201, 491 (1995).
40. (a) J. J. P. Stewart, J. Comput. Chem. 10, 221 (1989);
41. (b) B. Kallies and R. Mitzner, J. Mol. Model. 1, 68 (1995), and references cited therein.
42. E. N. Denisov, V. Shustryakov, E. N. Nikolaev, F. J. Winkler and R. Medina, (a) Proceedings of the 44th ASMS Conference, Portland, OR, 1996, p. 1414.
43. (b) Int. J. Mass Spectrom. Ion Proc. in press (1997).
44. M. T. Bowers, Gas Phase Ion Chemistry, Vol. 2, Chap. 9. Academic, New York (1979).
45. E. N. Nikolaev and T. McMahon, personal communication (1995).
46. F. J. Winkler, R. Medina, J. Winkler and H. Krause, unpublished (1996).
47. R. Zhang and C. Lifshitz. J. Phys. Chem. 100, 960 (1996).
48. R. Süβmuth, G. Jung, F. J. Winkler and R. Medina, unpublished (1996).