Intermolecular interactions characterized by nuclear Overhauser effects

Progress in Nuclear Magnetic Resonance Spectroscopy

Volumn 30, Issue 1-2, 1997, Pages 1-38

  Mo, Huaping ^a   Pochapsky, Thomas C ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Chiral recognition; Host guest complex; Intermolecular interaction; Ion pair; Molecular recognition; NOE; Nuclear quadrupole; Nuclear relaxation; Organolithium; Solvation

Indexed keywords

COMPLEXATION; HYDROGEN BONDS; IONS; MACROMOLECULES; MAGNETIC FIELD EFFECTS; MAGNETIZATION; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE;

INTERMOLECULAR INTERACTIONS; NUCLEAR OVERHAUSER EFFECTS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0031098539     PISSN: 00796565     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0079-6565(96)01036-9     Document Type: Review

References (145)

1. I. Solomon, Phys. Rev., 99 (1955) 559.
2. R. Kaiser, J. Chem. Phys., 42 (1965) 838.
3. D. Neuhaus and M. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, 1989.
4. G.M. Clore and A.M. Gronenborn, J. Magn. Reson., 53 (1983) 423.
5. F. Ni, Progr. NMR Spectrosc., 26 (1994) 517.
6. G.M. Lippens, C. Cerf and K. Hallenga, J. Magn. Reson., 99 (1992) 268.
7. J.H. Noggle and R.E. Schirmer, The Nuclear Overhauser Effect: Chemical Applications, Academic Press, New York, 1971.
8. A. Abragam, Principles of Nuclear Magnetism, Oxford University Press, Oxford, 1961, Chapter VIII.
9. S. Macura and R.R. Ernst, Mol. Phys., 41 (1980) 95.
10. J.K.M. Sanders and B.K. Hunter, Modern NMR Spectroscopy - A Guide for Chemists, Oxford University Press, Oxford, 2nd edn., 1993, p. 176.
11. T.C. Pochapsky and P.M. Stone, J. Am. Chem. Soc., 112 (1990) 6714.
12. T.C. Pochapsky, A-P. Wang and P.M. Stone, J. Am. Chem. Soc., 115 (1993) 11084.
13. P. Balaram, A.A. Bothner-By and E. Breslow, Biochemistry, 12 (1973) 4695.
14. M. Borzo and G.E. Maciel, J. Magn. Reson., 43 (1981) 175.
15. G. Wagner and K. Wüthrich, J. Magn. Reson., 33 (1979) 675.
16. S.L. Gordon and K. Wüthrich, J. Am. Chem. Soc., 100 (1978) 7094.
17. L. Emsley, Meth. Enzym., 239 (1994) 207.
18. C.M. Dobson, E.T. Olejniczak, F.M. Poulsen and R.G. Ratcliffe, J. Magn. Reson., 48 (1982) 97.
19. J. Stonehouse, P. Adell, J. Keeler and A.J. Shaka, J. Am. Chem. Soc., 116 (1994) 6037.
20. K. Stott, J. Stonehouse, J. Keeler, T. Hwang and A.J. Shaka, J. Am. Chem. Soc., 117 (1995) 4199.
21. Q.N. Van and A.J. Shaka, J. Magn. Reson. A, 119 (1996) 295.
22. A.A. Bothner-By, R.L. Stephens, J.-M. Lee, C.D. Warren and R.W. Jeanloz, J. Am. Chem. Soc., 106 (1984) 811.
23. H. Desvaux, P. Berthault, N. Birlirakis and M. Goldman, J. Magn. Reson. A, 108 (1994) 219.
24. A. Bax and D.G. Davis, J. Magn. Reson., 63 (1985) 207.
25. P.L. Rinaldi, J. Am. Chem. Soc., 105 (1983) 5167.
26. C. Yu and G.C. Levy, J. Am. Chem. Soc., 105 (1983) 6694.
27. C. Yu and G.C. Levy, J. Am. Chem. Soc., 106 (1984) 6533.
28. L. Kay, D.A. Torchia and A. Bax, Biochemistry, 28 (1989) 8972.
29. G. Wider, C. Weber and K. Wuthrich, J. Am. Chem. Soc., 113 (1991) 4676.
30. E.T. Olejniczak and S.W. Fesik, J. Am. Chem. Soc., 116 (1994) 2215.
31. I. Furó, P. Mutzenhardt and D. Canet, J. Am. Chem. Soc., 117 (1995) 10405.
32. R.J. Bergeron, M.A. Channing and K.A. McGovern, J. Am. Chem. Soc., 100 (1978) 2878.
33. H. Gunther, D. Moskau, P. Bast and D. Schmalz, Angew. Chem., Int. Ed. Engl., 26 (1987) 1212.
34. W. Bauer, in A.-M. Sapse and P.v.R. Schleyer (eds.), Lithium Chemistry, Wiley, New York, 1995, p. 125.
35. W. Bauer and P.v.R. Schleyer, Magn. Reson. Chem., 26 (1988) 827.
36. W. Bauer, P.A.A. Klusener, S. Harder, J.A. Kanters, A.J.M. Duisenberg, L. Brandsma and P.v.R. Scheyler, Organometallics, 7 (1988) 552.
37. W. Bauer, T. Clark and P.v.R. Schleyer, J. Am. Chem. Soc., 109 (1987) 970.
38. A.G. Avent, C. Eaborn, M.N.A. El-Kheli, M.E. Molla, J.D. Smith and A.C. Sullivan, J. Am. Chem. Soc., 108 (1986) 3854.
39. W. Bauer, G. Müller, R. Pi and P.v.R. Schleyer, Angew. Chem., Int. Ed. Eng., 25 (1986) 1103.
40. D. Hoffman, W. Bauer and P.v.R. Schleyer, J. Chem. Soc. Chem. Commun. (1990) 208.
41. J.W. Akitt, in J. Mason (ed.), Multinuclear NMR, Plenum Press, New York, 1987, p. 212, and references cited therein.
42. R. Zerger, W. Rhine and G.D. Stucky, J. Am. Chem. Soc., 96 (1974) 5441.
43. T.E. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 88 (1966) 307.
44. G. Hilmersson and Ö. Davidsson, Organometallics, 14 (1995) 912.
45. M. Eiermann and K. Hafner, J. Am. Chem. Soc., 114 (1992) 135.
46. L.D. Field, M.G. Gardiner, B.A. Messerle and C.L. Raston, Organometallics, 11 (1992) 3566.
47. W. Bauer and L. Lochmann, J. Am. Chem. Soc., 114 (1992) 7482.
48. A. Bagno, C. Comuzzi and G. Scorrano, J. Am. Chem. Soc., 116 (1994) 916.
49. C.M. Starks, C.L. Liotta and M. Halpern, Phase Transfer Catalysis, Chapman and Hall, New York, 1994.
50. M. Szwarc, Ions and Ion Pairs in Organic Reactions, Vols. 1 and 2, Wiley Interscience, New York, 1972, 1974.
51. T.E. Hogen-Esch, Adv. Phys. Org. Chem., 15 (1977) 153.
52. C. Reichardt, Solvent and Solvent Effects in Organic Chemistry, VCH, Weinheim, 2nd edn., 1988.
53. H.W. Vos, C. MacLean and N.H. Velthorst, J. Chem. Soc. Farad. Trans. II, 73 (1977) 327.
54. J. Van der Kooij, N.H. Velhorst and C. MacLean, Chem. Phys. Lett., 12 (1972) 596.
55. J.B. Grutzner, J.M. Lawlor and L.M. Jackman, J. Am. Chem. Soc., 94 (1972) 2306.
56. N.-Y. Tsao and Y.-Y. Lim, Austr. J. Chem., 34 (1981) 2321.
57. N. Chen, P.J. Witton, C.E. Holloway and I.M. Walker, J. Coord. Chem., 19 (1988) 113.
58. G.N. La Mar, J. Chem. Phys., 43 (1965) 235.
59. Y.Y. Lim and R.S. Drago, J. Am. Chem. Soc., 94 (1972) 84.
60. R.V. Honeychuck and W.H. Hersh, J. Am. Chem. Soc., 111 (1989) 6056.
61. H. Kessler and M. Feigel, Acc. Chem. Res., 15 (1982) 2.
62. J.M. Miller and J.H. Clark, J. Chem. Soc. Chem. Commun. (1982) 1318.
63. K. Radley, Mol. Cryst. Liq. Cryst. Lett. Sect., 6 (1989) 203.
64. F.D. Sacher, M. Holz and H.G. Hertz, J. Magn. Reson. A, 103 (1993) 61.
65. H. Suezawa, N. Horiike, S. Yamazaki, H. Kamachi and M. Hirota, J. Phys. Chem., 95 (1991) 10787.
66. B. Lindman, H. Wennerström and S. Forsén, J. Phys. Chem., 96 (1992) 5669.
67. M. Holz, R. Grunder, A. Sacco and A. Meleleo, J. Chem. Soc., Faraday Trans., 89 (1993) 1215.
68. M. Holz and M. Sörensen, Ber. Bunsenges. Phys. Chem., 96 (1992) 1441.
69. M. Holz and K.J. Patil, Ber. Bunsenges. Phys. Chem., 95 (1991) 107.
70. P.M. Stone, T.C. Pochapsky and E. Callegari, J. Chem. Soc., Chem Commun., (1992) 178.
71. M.T. Reetz, S. Hütte and R. Goddard, J. Am. Chem. Soc., 115 (1993) 9339.
72. R.H. Crabtree, P.E.M. Siegbahn, O. Eisenstein, A.L. Rheingold and T.F. Koetzle, Acc. Chem. Res., 29 (1996) 348.
73. D.T. Copenhafer and C.A. Kraus, J. Am. Chem. Soc., 73 (1951) 4557.
74. S.S. Pochapsky, H. Mo and T.C. Pochapsky, J. Chem. Soc. Chem. Commun., (1995) 2513.
75. S. Juliá, A. Ginebreda, J. Guixer, J. Masana, A. Tomás and S. Collona, J. Chem. Soc., Perkin Trans. I, (1981) 574.
76. T.C. Pochapsky, P.M. Stone and S.S. Pochapsky, J. Am. Chem. Soc., 113 (1991) 1460.
77. I. Lampre, D. Markovitsi, N. Birlirakis and M. Veber, Chem. Phys., 202 (1996) 107.
78. R.A. Mantz, P.C. Trulove, R.T. Carlin and R.A. Osteryoung, Inorg. Chem., 34 (1995) 3846.
79. Z. Lin and G.B. Schuster, J. Org. Chem., 59 (1994) 1119.
80. W. Bauer, Magn. Reson. Chem., 29 (1991) 494.
81. F. Wehrli, J. Magn. Reson., 25 (1977) 575.
82. H-J. Schneider, Recl. Trav. Chim. Pays-Bas, 112 (1993) 412.
83. R.J. Bergeron and M.A. Channing, J. Am. Chem. Soc., 101 (1979) 2511.
84. C. Jaime, J. Redondo, F Sánchez-Ferrando and A. Virgili, J. Org. Chem., 55 (1990) 4772.
85. D. Greatbanks and R. Pickford, Magn. Reson. Chem., 25 (1987) 208.
86. M. Watanabe, H. Nakamura and T. Matsuo, Bull. Chem. Soc. Jpn., 65 (1992) 164.
87. C.D. Gutsche, M. Iqbal and I. Alam, J. Am. Chem. Soc., 109 (1987) 4314.
88. D.F. Nogales, J-S. Ma and D.A. Lightner, Tetrahedron, 49 (1993) 2361.
89. R. Foster, Chem. Br., 12 (1976) 18.
90. C.L. Fisk, E.D. Becker, H.T. Miles and T.J. Pinnavaia, J. Am. Chem. Soc., 104 (1992) 3307.
91. R.E. Hoffman and M. Rabinovitz, Magn. Reson. Chem., 31 (1993) 1051.
92. J.C. Barnes and W. Golnazarians, Acta Crystallogr., Sect. C, 43 (1987) 549.
93. P-L. Anelli, M. Asakawa, P.R. Ashton, G.R. Brown, W. Hayes, O. Kocian, S.R. Pastor, J.F. Stoddart, M.S. Tolley, A.J.P. White and D.J. Williams, J. Chem. Soc., Chem Commun., (1995) 2541.
94. G. Zieger, R. Konrat and H. Sterk, Magn. Reson. Chem., 30 (1992) S3.
95. N. Marchettini, G. Valensin and E. Gaggelli, Biophys. Chem., 36 (1990) 65.
96. S.E. Fuller, B.E. Mann and J.F. Stoddart, J. Chem. Soc., Chem. Commun., (1982) 1096.
97. D.G. Reid, S.A. Salisburg and D.H. Williams, Biochemistry, 22 (1983) 1373.
98. D.H. Williams, M.P. Williamson, D.W. Butcher and S.J. Hammond, J. Am. Chem. Soc., 105 (1983) 1332.
99. W.H. Pirkle and T.C. Pochapsky, Chem. Rev., 89 (1989) 347.
100. W.H. Pirkle and T.C. Pochapsky, J. Am. Chem. Soc., 108 (1986) 5627.
101. W.H. Pirkle and T.C. Pochapsky, J. Am. Chem. Soc., 109 (1987) 5975.
102. W.H. Pirkle, J.A. Burke and S.R. Wilson, J. Am. Chem. Soc., 111 (1989) 9222.
103. W.H. Pirkle, P.G. Murray, D.J. Rausch and S.T. McKenna, J. Org. Chem., 61 (1996) 4769.
104. W.H. Pirkle, P.G. Murray and S.R. Wilson, J. Org. Chem., 61 (1996) 4775.
105. W.H. Pirkle and S.R. Selness, J. Org. Chem., 60 (1995) 3252.
106. Y. Liu, Ph.D. Thesis, University of Illinois, 1996.
107. J. Rebek, Jr., B. Askew, P. Ballester, C. Buhr, A. Costero, S. Jones and K. Williams, J. Am. Chem. Soc., 109 (1987) 6866.
108. A. Galan, J. de Mendoza, C. Toiron, M. Bruix, G. Deslongchamps and J. Rebek, Jr. J. Am. Chem. Soc., 113 (1991) 9424.
109. C.T. Seto and G.M. Whitesides, J. Am. Chem. Soc., 113 (1991) 712.
110. T. Shibata, J. Uzawa and Y. Sugiura, Chem. Phys. Lipids, 33 (1983) 1.
111. D. Canet, N. Mahieu and P. Tekely, J. Am. Chem. Soc., 114 (1992) 6190.
112. N. Mahieu, P. Tekely and D. Canet, J. Phys. Chem., 97 (1993) 2764.
113. A.J. Belmajdoub, N. Mahieu, P. Tekely and D. Canet J. Phys. Chem., 96 (1992) 1011.
114. X. Zhang, K. Takegoshi and K. Hikichi, Macromolecules, 25 (1992) 4871.
115. A. Natansohn and A. Eisenberg, Macromolecules, 20 (1987) 323.
116. M.W. Crowther, I. Cabasso and G.C. Levy, Macromolecules, 21 (1988) 2924.
117. P.A. Mirau, H. Tanaka and F.A. Bovey, Macromolecules, 21 (1988) 2929.
118. P.A. Mirau and F.A. Bovey, Macromolecules, 23 (1990) 4548.
119. X. Zhang, K. Takegoshi and K. Hikichi, Polym. J., 23 (1991) 79.
120. P.R. Rajamohanan, S. Ganapathy, S.S. Ray, M.V. Badiger and R.A. Mashelkar, Macromolecules, 28 (1995) 2533.
121. S. Ganapathy, S.S. Ray, P.R. Rajamohanan and R.A. Mashelkar, J. Chem. Phys., 103 (1995) 6783.
122. C.F. Jensen, S. Deshmukh, H.J. Jackobson, R.R. Inners and P.D. Ellis, J. Am. Chem. Soc., 103 (1981) 3659.
123. C.C. Bryden and C. Reilly, J. Am. Chem. Soc., 104 (1982) 2697.
124. X. Yan, J. Fan, X. Xu, D. Wang, G. Nie and B. Qian, Magn. Reson. Chem., 29 (1991) 1092.
125. M. Tokles, F.J. Swiecinski and P.L. Rinaldi, J. Magn. Reson., 91 (1991) 222.
126. G.C. Levy, P.L. Rinaldi and J.T. Bailey, J. Magn. Reson., 40 (1980) 167.
127. H.B. Seba and B. Ancian, J. Chem. Soc. Chem. Commun. 996 (1990).
128. H.B. Seba and B. Ancian, J. Magn. Reson., 84 (1989) 177.
129. J. Tropp, J. Chem. Phys., 72 (1980) 6035.
130. G. Lipari and A. Szabo, J. Am. Chem. Soc., 104 (1982) 4546.
131. G. Lipari and A. Szabo, J. Am. Chem. Soc., 104 (1982) 4559.
132. P.E.J. Sanderson, J.D. Kilburn and C.W. Still, J. Am. Chem. Soc., 111 (1989) 8314.
133. R.M. Izatt, C.Y. Zhu, N.K. Dalley, J.C. Curtis, X. Kou and J.S. Bradshaw, J. Phys. Org. Chem., 5 (1992) 656.
134. T. Want, J.S. Bradshaw, J.C. Curtis, P. Huszthy and P.M. Izatt, J. Inclus. Phenom. Mol. Recog. Chem, 16 (1993) 113.
135. E.A., M. Wiese, H.L. Chi, H. Cordes and J.K. Seydel, Quant. Struc.-Activ. Relat., 11 (1992) 364.
136. G. Uccello-Barretta, C. Rosini, D. Pini and P. Salvadori, J. Am. Chem. Soc., 112 (1990) 2707.
137. F.W. Wehrli, J. Magn. Reson., 23 (1976) 527.
138. F.W. Wehrli, J. Magn. Reson., 23 (1976) 181.
139. E.E. Simanek, M.I.M. Wazeer, J.P. Mathias, G.M. Whiteside, J. Org. Chem., 59 (1994) 4904.
140. K. Araki, H. Shimizu and S. Shinkai, Chem. Lett. 205 (1993).
141. J.L. White and P. Mirau, Macromolecules, 26 (1993) 3049.
142. L.A. Paquette, M.R. Sivik, W. Bauer and P.v.R. Scheyler, Organometallics, 13 (1994) 4919.
143. W. Bauer, W.R. Winchester and P.v.R. Schleyer, Organometallics, 6 (1987) 2371.
144. S. Berger and F. Müller, Chem. Ber., 128 (1995) 799.
145. W. Bauer, M. Feigel, G. Müller and P.v.R. Schleyer, J. Am. Chem. Soc., 110 (1988) 6033.