Redirecting secondary bonds to control molecular and crystal properties of an iodosyl- and an iodylbenzene

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 2007-2010

  Macikenas, Dainius ^a   Skrzypczak Jankun, Ewa ^b   Protasiewicz, John D ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b UNIVERSITY OF TOLEDO   (United States)

Author keywords

Hydrogen bonds; Hypervalent compounds; Secondary bonds; Solid state structures

Indexed keywords

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MOLECULAR DYNAMICS; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0034595885     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<2007::AID-ANIE2007>3.0.CO;2-Z     Document Type: Article

References (67)

1. N.W. Alcock, Adv. Inorg. Chem. Radiochem. 1972, 15, 1-58; The secondary I ⋯ O bonds discussed here are different from the I ⋯ O charge-transfer bonds discussed in O. Hassel, C. Rommong, Quart. Rev. Chem. Soc. 1962, 16, 1-18 and O. Hassel, Science 1970, 170, 497-502. In reality, a continuum of intermolecular bonding types and interactions exist. See also P. Pyykkö, Chem. Rev. 1997, 97, 597-636.
2. N.W. Alcock, Adv. Inorg. Chem. Radiochem. 1972, 15, 1-58; The secondary I ⋯ O bonds discussed here are different from the I ⋯ O charge-transfer bonds discussed in O. Hassel, C. Rommong, Quart. Rev. Chem. Soc. 1962, 16, 1-18 and O. Hassel, Science 1970, 170, 497-502. In reality, a continuum of intermolecular bonding types and interactions exist. See also P. Pyykkö, Chem. Rev. 1997, 97, 597-636.
3. N.W. Alcock, Adv. Inorg. Chem. Radiochem. 1972, 15, 1-58; The secondary I ⋯ O bonds discussed here are different from the I ⋯ O charge-transfer bonds discussed in O. Hassel, C. Rommong, Quart. Rev. Chem. Soc. 1962, 16, 1-18 and O. Hassel, Science 1970, 170, 497-502. In reality, a continuum of intermolecular bonding types and interactions exist. See also P. Pyykkö, Chem. Rev. 1997, 97, 597-636.
4. N.W. Alcock, Adv. Inorg. Chem. Radiochem. 1972, 15, 1-58; The secondary I ⋯ O bonds discussed here are different from the I ⋯ O charge-transfer bonds discussed in O. Hassel, C. Rommong, Quart. Rev. Chem. Soc. 1962, 16, 1-18 and O. Hassel, Science 1970, 170, 497-502. In reality, a continuum of intermolecular bonding types and interactions exist. See also P. Pyykkö, Chem. Rev. 1997, 97, 597-636.
5. a) G. A. Landrum, R. Hoffmann, Angew. Chemie 1998, 110, 1989-1992; Angew. Chem. Int. Ed. 1998, 37, 1887-1890;
6. a) G. A. Landrum, R. Hoffmann, Angew. Chemie 1998, 110, 1989-1992; Angew. Chem. Int. Ed. 1998, 37, 1887-1890;
7. b) G. A. Landrum, N. Goldberg, R. Hoffmann, R. M. Minyaev, New J. Chem. 1998, 22, 883-890.
8. J. Starbuck, N. C. Norman, A. G. Open, New J. Chem. 1999, 23, 969-972.
9. R. J. Batchelor, T. Birchall, J. F. Sawyer, Inorg. Chem. 1986, 25, 1415-1420.
10. a) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26;
11. b) U. H. Hirt, B. Spingler, T. Wirth, J. Org. Chem. 1998, 63, 7674-7679.
12. Some reviews: a) T. Kitamura, Y. Fujiwara, Org. Prep. Proced. Int. 1997, 29, 409-458;
13. b) A. Varvoglis, Tetrahedron 1997, 53, 1179-1255;
14. c) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178;
15. d) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, New York, 1992;
16. e) R. M. Moriarty, O. Prakash, Acc. Chem. Res. 1986, 19, 244-250;
17. f) A. Varvoglis, Synthesis 1984, 709-726;
18. g) G. F. Koser in The Chemistry of the Functional Groups, Supplement D (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1983, pp. 721-811.
19. a) F. Lichtenberger, W. Nastainczyk, V. Ullrich, Biochem. Biophys. Res. Commun. 1976, 70, 939-946;
20. b) F. Lichtenberger, V. Ullrich, Microsomes and Drug Oxidations (Ed.: V. Ullrich), Pergamon, New York. 1977, pp. 218-223;
21. c) J. T. Groves, T. E. Nemo, R. S. Myers, J. Am. Chem. Soc. 1979, 101, 1032-1033.
22. Some recent reviews: a) Y. Moro-oka, Catal. Today 1998, 45, 3-12;
23. b) Y. Moro-oka, M. Akita, Catal. Today 1998, 41, 327-338;
24. c) M. Lautens, W. Klute, W. Tam. Chem. Rev. 1996, 96, 49-92;
25. d) J. T. Groves, Y.-Z. Han in Models and Mechanisms of Cytochrome P-450 Action (Ed.: P. O. D. Montellano), Plenum Press, New York, 1995, pp. 1-45;
26. e) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994:
27. f) D. H. R. Barton, A. E. Martell, D. T. Sawyer, The Activation of Dioxygen and Homogeneous Catalytic Oxidation, Plenum Press, New York, 1993;
28. g) I. Ojima, Catalytic Asymmetric Synthesis, VCH, New York, 1993;
29. h) R. A. Aitken, S. N. Kilényi, Asymmetric Synthesis, Blackie, New York, 1992;
30. i) D. Ostovic, T. C. Bruice, Acc. Chem. Res. 1992, 25, 314-320;
31. j) R. H. Holm, J. P. Donahue, Polyhedron 1993, 12, 571-589;
32. k) R. H. Holm, Chem. Rev. 1987, 87, 1401-1449.
33. C. Willgerodt, Chem. Ber. 1892, 25, 3494-3502.
34. a) W. E. Dasent, T. C. Waddington, J. Chem. Soc. 1960, 2429-2432;
35. b) W. E. Dasent, T. C. Waddington, J. Chem. Soc. 1960, 3350-3356;
36. c) R. Bell, K. J. Morgan, J. Chem. Soc. 1960, 1209-1214;
37. d) H. Siebert, M. Handrich, Z. Anorg. Allg. Chem. 1976, 426, 173-183;
38. e) B. S. Ehrlich, M. Kaplan, J. Chem. Phys. 1971, 54, 612-620;
39. f) J. V. Carey, P. A. Chaloner, K. R. Seddon, M. Taylor, J. Chem. Res. (S) 1996, 156-157;
40. g) C. J. Carmalt, J. G. Crossley, J. G. Knight, P. Lightfoot, A. Martin, M. P. Muldowney, N. C. Norman, A. G. Orpen, J. Chem. Soc. Chem. Commun. 1994, 2367-2368.
41. H. W. Richter, B. R. Cherry, T. D. Zook, G. F. Koser, J. Am. Chem. Soc. 1997, 119, 9614-9623.
42. D. Macikenas, E. Skrzypczak-Jankun, J. D. Protasiewicz, J. Am. Chem. Soc. 1999, 121, 7164-7165.
43. 3 deuterium atom was located from the Fourier map and refined isotropically. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-137694 and CCDC-137693. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44) 1223-336-033: e-mail: deposit@ccdc.cam.ac.uk)..CCDC
44. For recent discussion of cyclic intramolecular O ⋯ X secondary bonds (X = chalcogen) see: R. M. Minyaev, V. I, Minkin, Can. J. Chem. 1998, 76, 776-788, and references therein.
45. V. V. Zhdankin, Rev. Heteroatom Chem. 1997, 17, 133-151.
46. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
47. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
48. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
49. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
50. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
51. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
52. Compound A: G. F. Koser, G. Sun, C. W. Porter, W. J. Youngs, J. Org. Chem. 1993, 58, 7310-7312; Compound B: T. M. Balthazor, J. A. Miles, B. R. Stults, J. Org. Chem. 1978, 43, 4538-4540; Compound C: E. Shefter, W. Wolf, J. Pharm. Sci. 1965, 54, 104-107; Compounds D, E. and I: ref. [20e]; Compound F: N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115-120; Compound G: P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589-591: Compound H: J. Z. Gougoutas, Cryst. Struct. Commun. 1981, 10, 489-494.
53. a) T. Steiner, New J. Chem. 1998, 1099-1103;
54. b) T. Steiner, Chem. Commun. 1997, 727-734;
55. c) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296.
56. Reported I-O bond lengths of 1.60 and 1.65 Å for para-chloroiodyl-benzene in E. M. Archer, Acta Cryst. 1948, I, 64-69 are probably not reliable.
57. "Iodonium ylide compositions and method for antimicrobial use": a) A. G. Relenyi, R. W. Walter, G. F. Koser (Dow Chemical Co., USA), EP160322B1, 1989; "Preparation of iodonium ylide antimicrobial compounds":
58. b) A. G. Relenyi, W. J. Kruper, Jr., R. W. Waller, R. B. Shankar, A. P. Zelinko, G. F. Koser (Dow Chemical Co., USA), EP22S478B1, 1990; "Iodones and methods for antimicrobial use": A. G. Relenyi, G. F. Koser, R. W. Walter, Jr., W. S. Kruper, Jr., R. B. Shankar, A. P. Zelinko (Dow Chemical Co., USA), US5106407, 1992.
59. b) A. G. Relenyi, W. J. Kruper, Jr., R. W. Waller, R. B. Shankar, A. P. Zelinko, G. F. Koser (Dow Chemical Co., USA), EP22S478B1, 1990; "Iodones and methods for antimicrobial use": A. G. Relenyi, G. F. Koser, R. W. Walter, Jr., W. S. Kruper, Jr., R. B. Shankar, A. P. Zelinko (Dow Chemical Co., USA), US5106407, 1992.
60. Some recent work: a) R. A. Moss, H. Morales-Rojas, H. Zhang, B.-D. Park, Langmuir 1999, 15, 2738-2744;
61. b) A. R. Katritzky, G. P. Savage, J. K. Gallos, H. D. Durst, J. Chem. Soc. Perkin Trans. 2 1990, 1515-1518;
62. c) D. R. Leslie, S. Pantelidis, Aust. J. Chem. 1990, 43, 937-943;
63. d) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, J. R. Ward, J. Org. Chem. 1990, 55, 5202-5205;
64. e) A. R. Katritzky, G. P. Savage, G. J. Palenik, K. Qian, Z. Zhang, H. D. Durst, J. Chem. Soc. Perkin Trans. 2 1990, 1657-1661;
65. f) R. A. Moss, K. Bracken, T. J. Emge, J. Org. Chem 1995, 60, 7739-7746;
66. g) R. A. Moss, S. Bose, K. Krogh-Jespersen, J. Phys. Org. Chem. 1997, 10, 27-32;
67. h) R. A. Moss, Chem. Commun. 1998, 1559-1560.