Molecular self-assemblies. 5. Analysis of the vector properties of hydrogen bonding in crystal engineering

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8433-8443

  Perlstein, Jerry ^a   Steppe, Kevin ^a   Vaday, Shai ^a   Ndip, Edmund Moses N ^b  

^a UNIVERSITY OF ROCHESTER   (United States)

^b HAMPTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CRYSTALLOGRAPHY; MOLECULAR DYNAMICS; PHYSICS;

EID: 0029840672     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9543412     Document Type: Article

References (83)

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2. For leading references, see the special issue dedicated to Margaret Etter, "Structure and Chemistry of the Organic Solid State": Chem. Mater. 1994, 6, 1087-1461. See also the following reviews: (a) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (b) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383-395. (c) Zaworotko, M. J. Chem. Soc. Rev. 1994, 283-288. (d) Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357. (e) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 397-407.
3. For leading references, see the special issue dedicated to Margaret Etter, "Structure and Chemistry of the Organic Solid State": Chem. Mater. 1994, 6, 1087-1461. See also the following reviews: (a) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (b) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383-395. (c) Zaworotko, M. J. Chem. Soc. Rev. 1994, 283-288. (d) Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357. (e) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 397-407.
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29. For example, weaker C-H⋯O bond vectors have been invoked which we do not consider in this paper. For discussions on this type of interaction, see the following classic papers: (a) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (b) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070. For a review, see: Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. For quantum chemical treatments, see, for example: (a) Turi, L.; Dannenberg, J. J. J. Am. Chem. Soc. 1994, 116, 8714-8721. (b) Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754.
30. For example, weaker C-H⋯O bond vectors have been invoked which we do not consider in this paper. For discussions on this type of interaction, see the following classic papers: (a) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (b) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070. For a review, see: Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. For quantum chemical treatments, see, for example: (a) Turi, L.; Dannenberg, J. J. J. Am. Chem. Soc. 1994, 116, 8714-8721. (b) Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754.
31. For example, weaker C-H⋯O bond vectors have been invoked which we do not consider in this paper. For discussions on this type of interaction, see the following classic papers: (a) Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052-4064. (b) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070. For a review, see: Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. For quantum chemical treatments, see, for example: (a) Turi, L.; Dannenberg, J. J. J. Am. Chem. Soc. 1994, 116, 8714-8721. (b) Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754.
32. Perlstein, J. J. Am. Chem. Soc. 1994, 116, 11420-11432.
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49. Fortran routines for computing this energy as interfaces to the CHEMX/CHEMLIB molecular modeling package are available from the authors upon request. Contact the authors at internet address perlstein@chem.chem.rochester.edu.
50. CHEMX is a molecular modeling program developed and distributed by Chemical Design Ltd., Roundway House, Cromwell Park, Chipping Norton, Oxfordshire OX7 5SR, U.K. CHEMLIB is a CHEMX interface which allows the user to link subroutines to CHEMX.
51. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991; p 95.
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53. (b) Allen, F. H.; Kennard, O.; Taylor, R. Acc. Chem. Res. 1983, 16, 146-153.
54. Refcodes are from the Cambridge Structural Database and are as follows. (a) PAGTIA: Dado, G. P.; Desper, J. M.; Holmgren, S. K.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4834. (b) BENZAC02: Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215. BAGWUB: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891. BAGXAI: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891.
55. Refcodes are from the Cambridge Structural Database and are as follows. (a) PAGTIA: Dado, G. P.; Desper, J. M.; Holmgren, S. K.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4834. (b) BENZAC02: Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215. BAGWUB: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891. BAGXAI: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891.
56. Refcodes are from the Cambridge Structural Database and are as follows. (a) PAGTIA: Dado, G. P.; Desper, J. M.; Holmgren, S. K.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4834. (b) BENZAC02: Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215. BAGWUB: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891. BAGXAI: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891.
57. Refcodes are from the Cambridge Structural Database and are as follows. (a) PAGTIA: Dado, G. P.; Desper, J. M.; Holmgren, S. K.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4834. (b) BENZAC02: Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215. BAGWUB: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891. BAGXAI: Smith, G.; Kennard, C. H. L. Acta Crystallogr., Sect. B 1981, 37, 1891.
58. For a thorough discussion of carboxylic acids and amides, see: (a) Leiserowitz, L. Acta Crystallogr. 1976, B32, 775-802.
59. (b) Leiserowitz, L.; Hagler, A. T. Proc. R. Soc. London, A 1983, 388, 133-175.
60. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
61. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
62. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
63. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
64. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
65. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
66. Refcodes are from the Cambridge Structural Database and are as follows. (a) AMBACO06: Hardy, G. E.; Kaska, W. C.; Chandra, B. P.; Zink, J. I. J. Am. Chem. Soc. 1981, 103, 1074. (b) FURDCB01: Semmingsen, D.; Nordenson, S.; Aasen, A. Acta Chem. Scand., Ser. A 1986, 40, 559. (c) SOJBIC: Mugnoli, A.; Carnasciali, M. M.; Sancassan, F.; Novi, M.; Petrillo, G. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1991, 47, 1916. (d) METCYT01: Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, 33, 3962. Refcodes are from the Cambridge Structural Database and are as follows. (a) BESKAL: Haisa, M.; Kashino, S.; Hanada, S.-I.; Tanaka, K.; Okazaki, S.; Shibagaki, M. Acta Crystallogr., Sect. B 1982, 38, 1480. (b) GLYCIN: Iitaka, Y. Acta Crystallogr. 1960, 13, 35. BAZFUD: Kojima, T.; Tanaka, I.; Ashida, T. Acta Crystallogr., Sect. B 1982, 38, 221.
67. The Monte Carlo software routines for packing chains, layers, and crystals is called PACK and has been interfaced to the CHEMX/CHEMLIB molecular modeling package. PACK is available upon request. Contact the authors at internet address perlstein@chem.chem.rochester.edu.
68. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
69. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
70. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
71. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
72. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
73. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
74. Refcodes are from the Cambridge Structural Database. Original references are as follows. (a) SIGBOZ: Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (b) WARXES: Reference 3f. (c) WARYIX: Reference 3f. DMOX-BA01: Bryan, R. F.; White, D. H. Act Crystallogr. 1982, B38, 1014-1016. (e) MESCON: Gupta, M. P.; Yadav, S. R. P. Acta Crystallogr. 1972, B28, 2682-2686. (f) CITKEV: Smith, G.; O'Reilly, E. J.; Kennard, C. H. L. Aust. J. Chem. 1983, 36, 2175-2183. (g) DACYEL: Ammon, H. L.; Prasad, S. M. Acta Crystallogr. 1985, C41, 921-924.
75. Willock, D. J.; Price, S. L.; Leslie, M.; Catlow, C. R. A. J. Comput. Chem. 1995, 16, 628-647.
76. Gavezzotti, A. J. Am. Chem. Soc. 1991, 113, 4622-4629.
77. For examples of packing in organometallic chemistry, see: (a) Braga, D.; Grepioni, F. Acc. Chem. Res. 1994, 27, 51-56. (b) Braga, D.; Grepioni, F.; Tedesco, E.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1995, 1215-1220.
78. For examples of packing in organometallic chemistry, see: (a) Braga, D.; Grepioni, F. Acc. Chem. Res. 1994, 27, 51-56. (b) Braga, D.; Grepioni, F.; Tedesco, E.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1995, 1215-1220.
79. See, for example, the following papers by the Whitten group: (a) Song, X.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7816-7817. (b) Chen, H.; Law, K.-Y.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257-7258. (c) Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 10340-10341.
80. See, for example, the following papers by the Whitten group: (a) Song, X.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7816-7817. (b) Chen, H.; Law, K.-Y.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257-7258. (c) Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 10340-10341.
81. See, for example, the following papers by the Whitten group: (a) Song, X.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7816-7817. (b) Chen, H.; Law, K.-Y.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257-7258. (c) Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 10340-10341.
82. Desiraju, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
83. J. Am. Chem. Soc. 1996, 118, 8444-8451