Crystal Structure of (Fluorosulfonyl)fluoroacetic Acid: A Novel Four-Center Hydrogen-Bond System Involving a C-H Donor

Inorganic Chemistry

Volumn 35, Issue 7, 1996, Pages 1912-1914

  Braden, Dale A ^a   Gard, Gary L ^a   Weakley, Timothy J R ^b  

^a PORTLAND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010026289     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic951315w     Document Type: Article

References (60)

1. Sokol'skii, G. A.; Pavlov, V. M.; Agafonov, S. A.; Knunyants, I. L. Chem. Heterocycl. Compd. (Engl. Tramsl.) 1973, 9, 164, Khim. Gemrotsikl. Soedin. 1973, 9, 178.
2. Sokol'skii, G. A.; Pavlov, V. M.; Agafonov, S. A.; Knunyants, I. L. Chem. Heterocycl. Compd. (Engl. Tramsl.) 1973, 9, 164, Khim. Gemrotsikl. Soedin. 1973, 9, 178.
3. Dmitriev, M. A.; Sokol'skii, G. A.; Knunyants, I. L. Khim. Nauka Prom. 1958, 3, 826, Dokl. Akad. Nauk SSSR 1959, 724, 581; Chem. Abstr. 1959, 53, 1121 Id.
4. Dmitriev, M. A.; Sokol'skii, G. A.; Knunyants, I. L. Khim. Nauka Prom. 1958, 3, 826, Dokl. Akad. Nauk SSSR 1959, 724, 581; Chem. Abstr. 1959, 53, 1121 Id.
5. Dmitriev, M. A.; Sokol'skii, G. A.; Knunyants, I. L. Khim. Nauka Prom. 1958, 3, 826, Dokl. Akad. Nauk SSSR 1959, 724, 581; Chem. Abstr. 1959, 53, 1121 Id.
6. Wagner, G.; Verfürth, U.; Herrmann, R.; Kniger, C. Z. Naturforsch., B 1994, 49, 1150.
7. Winter, R.; Gard, G. L.; Mews, R.; Noltemeyer M. J. Fluorine Chem. 1993, 60, 109.
8. Keszler, D. A.; Winter, R.; Gard, G. L. Eur. J. Solid State Inorg. Chem. 1992, 29, 835.
9. Desmarteau, D. D ; Pennington, W. T.; Sung, K.-S.; Zhu, S.-Z.; Scott, R. Eur. J. Solid Slate Inorg. Chem. 1991, 28, 905.
10. Polyakova, I. N.; Starikova, Z. A.; Parusnikov, B. V.; Inshakova, V. A.; Krasavin, I. A. J. Struct. Chem. (Engl. Transl.) 1990, 31, 454; Zh. Strukt. Khim. 1990, 31, 97.
11. Polyakova, I. N.; Starikova, Z. A.; Parusnikov, B. V.; Inshakova, V. A.; Krasavin, I. A. J. Struct. Chem. (Engl. Transl.) 1990, 31, 454; Zh. Strukt. Khim. 1990, 31, 97.
12. Polyakova, I. N.; Starikova, Z. A.; Parusnikov, B. V.; Krasavin, I. A. J. Struct. Chem. (Engl. Transl.) 1985, 26, 600, Zh. Strukt. Khim. 1985, 26, 125.
13. Polyakova, I. N.; Starikova, Z. A.; Parusnikov, B. V.; Krasavin, I. A. J. Struct. Chem. (Engl. Transl.) 1985, 26, 600, Zh. Strukt. Khim. 1985, 26, 125.
14. Yagulpolski, Y. L.; Savina, T. I.; Yufit, D. S , Struchkov, Y. T. Tetrahedron Lett. 1983, 24, 87.
15. Coxon, J. M.; Pojer, P. M.; Robinson, W. T.; Steel, P. J J. Chem. Soc., Chem. Commun. 1978, 111.
16. Camerman, A.; Smith, H. W.; Camerman, N. Acta Crystallogr., Sect. B 1979, 35, 2113.
17. 2O.
18. Sokol'skii, G. A.; Dmitriev, M. A.; Knunyants, I. L. Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transi) 1961, 572; Izv. Akad. Nauk SSSR. Ser. Khim. 1961, 621.
19. Sokol'skii, G. A.; Dmitriev, M. A.; Knunyants, I. L. Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transi) 1961, 572; Izv. Akad. Nauk SSSR. Ser. Khim. 1961, 621.
20. Gilraore, C. J. J. Appl. Crystallogr. 1984, 17, 42.
21. TEXSAN: Texray Program for Structure Analysis, version 5.0; 1989. Molecular Structures Corp.: 3200A Research Forest Dr., The Woodlands, TX 77381, 1989.
22. Cromer, D. T.; Waber, J. T. In International Tables for X-Ray Crystallography; Kynoch: Birmingham, England, 1974; Vol. IV. pp 71-147.
23. Braden, D. A.; Gard, G. L.; Oberhammer, H. Z Anorg. Allg. Chem. 1995, 621, 1849.
24. Kanters, J. A.; Kroon, J. Acta Crystallogr., Sect. B 1972, 28, 1946.
25. Rogers, R. D.; Kalyanaraman, B.; Dalton, M. S.; Smith, W.; Kispert, L. D.; Atwood, J. L. J. Cryst. Mol. Struct. 1981, 11, 105.
26. Nahringbauer, I.; Lundgren, J.-O.; Andersen, E. K. Acta Crystallogr, Sect. B 1979, 35, 508.
27. Nyburg, S. C.; Faerman, C. H. Acta Crystallogr., Sect. B 1985, 41, 274. The authors are grateful to a reviewer for this reference.
28. Jönsson, P -G. Acta Crystallogr., Sect. B 1971, 27, 893.
29. Eleev, A. F.; Ermolov, A. F.; Kutepov, A. P.; Sokol'skii, G. A., Chekholin, V. K Russ. J. Org. Chem. (Engl. Transl.) 1982, 18, 1467; Zh. Org. Khim. 1982, 18, 1679.
30. Eleev, A. F.; Ermolov, A. F.; Kutepov, A. P.; Sokol'skii, G. A., Chekholin, V. K Russ. J. Org. Chem. (Engl. Transl.) 1982, 18, 1467; Zh. Org. Khim. 1982, 18, 1679.
31. Chen, Q.-Y.; Wu, S.-W. J. Fluorine Chem. 1990, 47, 509.
32. Pouchert, C. J.; Behnke, J. The Aldrich Library of FT NMR Spectra; Aldrich Chemical. Milwaukee, WI, 1993; Vol. 1, p 791C.
33. Klöter, G.; Pritzkow, H.; Seppelt, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 942.
34. Winter, R.; Gard, G. L. Inorg. Chem. 1988, 27, 4329.
35. Aktaev, N P.; Sokol'skii, G. A.; Knunyants, I. L. Bull Acad. Sci. USSR, Chem. Ser. (Engl. Transl.) 1975, 2416; Izv. Akad. Nauk SSSR, Ser. Khim. 1975, 2530.
36. Aktaev, N P.; Sokol'skii, G. A.; Knunyants, I. L. Bull Acad. Sci. USSR, Chem. Ser. (Engl. Transl.) 1975, 2416; Izv. Akad. Nauk SSSR, Ser. Khim. 1975, 2530.
37. Eleev, A. F ; Sokol'skii, G. A.; Knunyants, I. L. Bull. Acad. Sci. USSR, Chem. Ser. (Engl. Transl.) 1980, 641; Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 892.
38. Eleev, A. F ; Sokol'skii, G. A.; Knunyants, I. L. Bull. Acad. Sci. USSR, Chem. Ser. (Engl. Transl.) 1980, 641; Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 892.
39. Green, R. D. Hydrogen Bonding by C-H Groups; Wiley New York, 1974.
40. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
41. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
42. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
43. Steiner, T., Saenger, W. J. Am. Chem. Soc. 1992, 114, 10146.
44. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1993, 115, 4540.
45. Umeyama, H.; Morokuma, K. J. Am. Chem. Soc. 1977, 99, 1316.
46. Banerjee, A.; Dattagupta, J. K ; Saenger, W.; Rabczenko, A. Acta Crystallogr., Sect. B 1977, 33, 90.
47. Smith, B. D.; Haller, K. J.; Shang, M. J. Org. Chem. 1993, 58, 6905.
48. Presspnch, M. R ; Willen, R. D.; Terjeson, R. J.; Winter, R., Gard, G L. Inorg. Chem. 1990, 29, 3058.
49. Taylor, R.; Kennard, O.; Versichel, W. J. Am. Chem. Soc. 1984, 106, 244.
50. Larsen, I. K. Acta Crystallogr., Sect. C 1985, 41, 749.
51. Brown, G. M.; Levy, H. A. Acta Crystallogr., Sect. B 1973, 29, 790
52. Schlemper, E. O.; Hamilton, W. C. J. Chem. Phys. 1966, 44, 4498.
53. Bracuti, A. J. J. Crystallogr. Spearosc. Res. 1993, 23, 669.
54. Cameron, T. S.; Knop, O.; Macdonald, L. A. Can. J. Chem. 1983, 61, 184.
55. Nassimbeni, L. R.; Rodgers, A. L. Inorg. Nucl Chem. Lett. 1975, 11, 757.
56. The searches of the Cambridge Crystallographic Database conducted by the authors of refs 31, 33. and 34 were not limited so as to exclude multicenter interactions for C-H⋯O hydrogen bondb. A CAS online search for examples of multicentered hydrogen bonds yielded no reports of four-center C-H⋯O systems in crystals. However, the existence of four-centered C-H⋯O hydrogen bonds has been invoked to explain NMR relaxation rates of metal tris(acetylacetonates) solvated by haloforms. See: Wang, P. L.; Lee, J. H.; Hwang. L. P. J. Phys. Chem. 1987, 91, 4856 and references therein.
57. Takusagawa, F.; Koetzle, T. F.; Srikrishnan, T.; Parthasarathy, R. Acta Crystallogr., Sect. B 1979, 35, 1388.
58. Dattagupta, J. K., Saenger, W., Bolewska, K.; Kulakowska, I. Acta Ciystailogr., Sect. B 1977, 33, 85.
59. Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197.
60. Desiraju, G. R.; Sharma, C. V. K. M. J. Chem. Soc., Chem. Commun. 1991, 1239.