Charge-transfer probes for molecular recognition via steric hindrance in donor-acceptor pairs

Journal of the American Chemical Society

Volumn 119, Issue 40, 1997, Pages 9393-9404

  Rathore, R ^a   Lindeman, S V ^a   Kochi, J K ^a  

^a University of Houston ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; AROMATIC HYDROCARBON; TETRANITROMETHANE;

ARTICLE; CRYSTALLOGRAPHY; ELECTRICITY; MOLECULAR RECOGNITION; REACTION ANALYSIS; SPECTROSCOPY; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 0030831029     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9720319     Document Type: Article

References (86)

1. (a) Meissner, R. S.; Rebek, J., Jr.; de Mendoza, J. Science 1995, 270, 1485.
2. (b) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 277, 487,
3. Wintner, E. A.; Rebek, J., Jr. Acta Chem. Scand. 1996, 50, 469 and references therein.
4. Mascal, M. Contemp. Org. Syn. 1994, 1, 1.
5. (e) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229.
6. (f) Still, C. W. Acc. Chem. Res. 1996, 29, 155.
7. (g) Hartshorn, C. M.; Steel, P. J. J. Chem. Soc., Chem. Commun. 1997, 541.
8. (a) Cram, D. J. Nature 1992, 356, 29.
9. (b) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009 and references therein.
10. (c) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89 and references therein.
11. (d) Lehn, J.-M. Pure Appl. Chem. 1994, 66, 1961.
12. (e) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1679.
13. (f) Metzger, A.; Lynch, V. M.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862.
14. (a) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
15. (b) Balzani, V. Tetrahedron 1992, 48, 10433.
16. (c) Stang, P. J.; Olenyuk, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 732. For donor - acceptor interactions in the solid state for crystal engineering, see: Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
17. (c) Stang, P. J.; Olenyuk, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 732. For donor - acceptor interactions in the solid state for crystal engineering, see: Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
18. (a) Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811.
19. (b) Mulliken, R. S.; Person, W. B. Molecular Complexes. A Lecture and Reprint Volume: Wiley: New York 1969.
20. Foster, R. Organic Charge-Transfer Complexes: Academic: New York, 1969.
21. Briegleb, G. Elektronen - Donator-Acceptor Komplexe; Springer: Berlin, 1961.
22. •-].
23. 2/ω which is especially applicable to planar donors and acceptors.
24. Charge-transfer interactions have been employed in the design/ synthesis of self-assembling catenanes, rotaxanes, and other molecular machines. See: (a) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart. J. F. Nature 1994, 369, 133. (b) Córdova, E.; Bissell, R. E.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033. (c) Asakawa, M; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26. (d) Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382.
25. Charge-transfer interactions have been employed in the design/ synthesis of self-assembling catenanes, rotaxanes, and other molecular machines. See: (a) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart. J. F. Nature 1994, 369, 133. (b) Córdova, E.; Bissell, R. E.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033. (c) Asakawa, M; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26. (d) Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382.
26. Charge-transfer interactions have been employed in the design/ synthesis of self-assembling catenanes, rotaxanes, and other molecular machines. See: (a) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart. J. F. Nature 1994, 369, 133. (b) Córdova, E.; Bissell, R. E.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033. (c) Asakawa, M; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26. (d) Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382.
27. Charge-transfer interactions have been employed in the design/ synthesis of self-assembling catenanes, rotaxanes, and other molecular machines. See: (a) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart. J. F. Nature 1994, 369, 133. (b) Córdova, E.; Bissell, R. E.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033. (c) Asakawa, M; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26. (d) Toki, A.; Yonemura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1993, 66, 3382.
28. For example, the highly colored trinitrobenzene/arene complexes have found extensive use in the purification and characterization of aromatic hydrocarbons owing to their ready crystallization with definite stoichiometry and sharp melting points. See: Weiss, J. J. Chem. Soc. 1942, 245. Powell, H. M.; Huse G.; Cook, P. W. J. Chem. Soc. 1943, 153. Parim, V. P. Russ. Chem. Rev. 1962, 31, 408.
29. For example, the highly colored trinitrobenzene/arene complexes have found extensive use in the purification and characterization of aromatic hydrocarbons owing to their ready crystallization with definite stoichiometry and sharp melting points. See: Weiss, J. J. Chem. Soc. 1942, 245. Powell, H. M.; Huse G.; Cook, P. W. J. Chem. Soc. 1943, 153. Parim, V. P. Russ. Chem. Rev. 1962, 31, 408.
30. For example, the highly colored trinitrobenzene/arene complexes have found extensive use in the purification and characterization of aromatic hydrocarbons owing to their ready crystallization with definite stoichiometry and sharp melting points. See: Weiss, J. J. Chem. Soc. 1942, 245. Powell, H. M.; Huse G.; Cook, P. W. J. Chem. Soc. 1943, 153. Parim, V. P. Russ. Chem. Rev. 1962, 31, 408.
31. The transitory contact charge-transfer complexes have been described by: Tamres, M.; Strong. R. L. In Molecular Association: Foster, R. F., Ed.; Academic: New York, 1979; Vol. 2, p 331ff.
32. (a) There are a few cases mentioned in the literature where electronrich but sterically congested donors such as hexaisopropylbenzene (Arnett, E. M.; Bollinger, J. M. J. Am. Chem. Soc. 1964, 86, 4729), hexacyclopropylbenzene (Usieli. V.; Victor. R.; Sarel, S. Tetrahedron Lett. 1976, 2705), and 1,4:5,8:9,12-triethanododecahydrotriphenylene (Komatsu, K.; Aonuma, S.; Jimbu, Y.; Tsuji, R.; Hirosawa. C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195), etc. show no charge-transfer absorptions with such commonly used electron acceptors as tetracyanoethylene (see: Merrifield, R. E.; Phillips, W. D. J. Am. Chem. Soc. 1950, 80, 2778 and Foster, R. in ref 4c, p 197). However, there is no systematic study extant in the literature to describe steric effects on donor - acceptor complexation.
33. (a) There are a few cases mentioned in the literature where electronrich but sterically congested donors such as hexaisopropylbenzene (Arnett, E. M.; Bollinger, J. M. J. Am. Chem. Soc. 1964, 86, 4729), hexacyclopropylbenzene (Usieli. V.; Victor. R.; Sarel, S. Tetrahedron Lett. 1976, 2705), and 1,4:5,8:9,12-triethanododecahydrotriphenylene (Komatsu, K.; Aonuma, S.; Jimbu, Y.; Tsuji, R.; Hirosawa. C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195), etc. show no charge-transfer absorptions with such commonly used electron acceptors as tetracyanoethylene (see: Merrifield, R. E.; Phillips, W. D. J. Am. Chem. Soc. 1950, 80, 2778 and Foster, R. in ref 4c, p 197). However, there is no systematic study extant in the literature to describe steric effects on donor - acceptor complexation.
34. (a) There are a few cases mentioned in the literature where electronrich but sterically congested donors such as hexaisopropylbenzene (Arnett, E. M.; Bollinger, J. M. J. Am. Chem. Soc. 1964, 86, 4729), hexacyclopropylbenzene (Usieli. V.; Victor. R.; Sarel, S. Tetrahedron Lett. 1976, 2705), and 1,4:5,8:9,12-triethanododecahydrotriphenylene (Komatsu, K.; Aonuma, S.; Jimbu, Y.; Tsuji, R.; Hirosawa. C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195), etc. show no charge-transfer absorptions with such commonly used electron acceptors as tetracyanoethylene (see: Merrifield, R. E.; Phillips, W. D. J. Am. Chem. Soc. 1950, 80, 2778 and Foster, R. in ref 4c, p 197). However, there is no systematic study extant in the literature to describe steric effects on donor - acceptor complexation.
35. (a) There are a few cases mentioned in the literature where electronrich but sterically congested donors such as hexaisopropylbenzene (Arnett, E. M.; Bollinger, J. M. J. Am. Chem. Soc. 1964, 86, 4729), hexacyclopropylbenzene (Usieli. V.; Victor. R.; Sarel, S. Tetrahedron Lett. 1976, 2705), and 1,4:5,8:9,12-triethanododecahydrotriphenylene (Komatsu, K.; Aonuma, S.; Jimbu, Y.; Tsuji, R.; Hirosawa. C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195), etc. show no charge-transfer absorptions with such commonly used electron acceptors as tetracyanoethylene (see: Merrifield, R. E.; Phillips, W. D. J. Am. Chem. Soc. 1950, 80, 2778 and Foster, R. in ref 4c, p 197). However, there is no systematic study extant in the literature to describe steric effects on donor - acceptor complexation.
36. (a) There are a few cases mentioned in the literature where electronrich but sterically congested donors such as hexaisopropylbenzene (Arnett, E. M.; Bollinger, J. M. J. Am. Chem. Soc. 1964, 86, 4729), hexacyclopropylbenzene (Usieli. V.; Victor. R.; Sarel, S. Tetrahedron Lett. 1976, 2705), and 1,4:5,8:9,12-triethanododecahydrotriphenylene (Komatsu, K.; Aonuma, S.; Jimbu, Y.; Tsuji, R.; Hirosawa. C.; Takeuchi, K. J. Org. Chem. 1991, 56, 195), etc. show no charge-transfer absorptions with such commonly used electron acceptors as tetracyanoethylene (see: Merrifield, R. E.; Phillips, W. D. J. Am. Chem. Soc. 1950, 80, 2778 and Foster, R. in ref 4c, p 197). However, there is no systematic study extant in the literature to describe steric effects on donor - acceptor complexation.
37. ox° of the other donors in Chart 1. see Tables 2 and 3.
38. red° -042: Körtüm. G.; Walz, H. Z. Electrochem. 1955, 59, 184.
39. red° -042: Körtüm. G.; Walz, H. Z. Electrochem. 1955, 59, 184.
40. red° -042: Körtüm. G.; Walz, H. Z. Electrochem. 1955, 59, 184.
41. red° -042: Körtüm. G.; Walz, H. Z. Electrochem. 1955, 59, 184.
42. red° is unmeasured.
43. red° is unmeasured.
44. red° is unmeasured.
45. red° is unmeasured.
46. Harding, T. T.; Wallwork, S. C. Acta Crystallogr. 1955, 8, 787. Also, see: Jones, N. D.; Marsh, R. E. Acta Crystallogr. 1962, 15, 809.
47. Harding, T. T.; Wallwork, S. C. Acta Crystallogr. 1955, 8, 787. Also, see: Jones, N. D.; Marsh, R. E. Acta Crystallogr. 1962, 15, 809.
48. 56
49. QUANTA (vers. 4.11) from Molecular Simulations, Inc., 16 New England Executive Park, Burlington, MA 081803-5297. See: Experimental Section for a brief description of the molecular modeling package.
50. (a) Benesi, H. A.; Hildebrand, J. J. J. Am. Chem. Soc. 1949, 71, 2703.
51. (b) Person, W. B. J. Am. Chem. Soc. 1965, 87, 167.
52. Foster, R. Molecular Complexes; Crane, Russak & Co.: New York, 1974; Vol. 2.
53. (a) Horner, L.; Merz, H. Ann. Chem. 1950, 89, 570.
54. (b) Rathore, R.; Kochi, J. K. Tetrahedron Lett, 1994, 35, 8577.
55. Bockman, T. M.; Perrier, S.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1993, 595.
56. Reichenback, G.; Santini, S.; Mazzucato, U. J. Chem. Soc., Faraday Trans. 1 1973, 49, 143.
57. CT is the "effective absorbance". see: Frey, J. E.; Andrews, A. M.; Ankoviac, G. G.; Beaman, D. N.; DuPont, L. E.; Elsner, T. E.; Lang, S. R.; Zwart, M. A. O.; Seagle, R. E.; Torreano, L. A. J. Org. Chem. 1990, 55, 606.
58. For the tetracyanoethylene data, see: Table 4.
59. 18
60. (a) Iverson, D. J.; Hunter, G.; Blount, J. F.; Damewood, Jr., J. R.; Mislow, K. J. Am. Chem. Soc. 1981, 103, 6073.
61. (b) See, also: Hunter, G.; Iverson, D. J; Mislow, K.; Blount, J. F. J. Am. Chem. Soc. 1980, 102, 5942.
62. Hunter, G.; Weakley, J. R.; Mislow, K.; Wong, M. G. J. Chem. Soc., Dalton Trans. 1986, 577.
63. DA are relatively invariant.
64. CT see: footnote 5.
65. -1 21a
66. CT values with increasing number of tert-butyl groups in Table 3 (see entries 1-4).
67. CT) derives from the transition moment which relates to the overlap integral of the donor and acceptor orbitals (see: Orgel, L. E.; Mulliken, R. S. J. Am. Chem. Soc. 1957, 79, 4839.
68. See: Staab, M. A.; Reibel, W. R. K.; Krieger, C. Chem. Ber. 1985, 118, 1230.
69. 24c due to the steric shielding of the dimethoxy-subsriruted benzene ring by the norbornane framework.
70. o, as measured electrochemically (see Experimental Section).
71. Molecular modeling calculations predict an optimum separation of ∼4 Å.
72. Maverick, E.; Trueblood, K. N.; Bekoe, D. A. Acta Crystallogr., Sect. B 1978, 34, 2777.
73. Kim, E. K.; Kochi, J. K. J. Am. Chem. Soc. 1991, 113, 4962.
74. 32 generally showed the nitrosonium to be sufficiently disordered to obscure the distinction between N and O. On the other hand, HEB and TET complexes showed no such disorder, and N bonding to the aromatic donor could be readily established.
75. (a) Brownstein, S.; Gabe, E.; Lee, F.; Tan, L. J. Chem. Soc., Chem. Commun. 1984, 1566.
76. (b) Brownstein, S.; Gabe, E.; Lee, F.; Piotrowski, A. Can. J. Chem. 1986, 64, 1661.
77. Brownstein, S.; Gabe, E.; Irish, B.; Lee, F.; Louie, B.; Piotrowski, A. Can. J. Chem. 1987, 65, 445.
78. Borodkin, G. I.; Nagi, S. M. Gatilov, Y. V.; Mamatyuk, V. I.; Mudrakovskii, T. L.; Shubin, V. G. Dokl. Akad. Nauk SSSR 1986, 288, 1364.
79. (e) Kim, E. K.: Kochi, J. K. J. Org. Chem. 1993, 58, 786.
80. +.
81. 9.21a
82. Sankararaman, S.; Haney, W. A.; Kochi, J. K. J. Am. Chem. Soc. 1984, 109, 5235 and 7824. Also, see: Kochi, J. K. Acta Chem. Scand. 1990, 44, 409.
83. Sankararaman, S.; Haney, W. A.; Kochi, J. K. J. Am. Chem. Soc. 1984, 109, 5235 and 7824. Also, see: Kochi, J. K. Acta Chem. Scand. 1990, 44, 409.
84. 2 as the acceptor moiety in TNM is unclear, an estimate of the separation is given by calculated distances of 2.9 and 3.0 Å of the oxygen pair to the aromatic plane in T. The corresponding distances in U are 3.3 at 3.6 Å.
85. Pasimeni, L.; Guella, G.; Corvaja, C.; Clemente, D. A; Vicentini, M. Mol. Cryst. Liq. Cryst. 1983, 91, 25.
86. Note that the presence of a pair of ortho substituents in PM-T and PE-T essentially precludes a planar biphenyl framework as in structure V.