A structural investigation of the N-B interaction in an o-(N,N-dialkylaminomethyl)arylboronate system

Journal of the American Chemical Society

Volumn 128, Issue 4, 2006, Pages 1222-1232

  Zhu, Lei ^a   Shabbir, Shagufta H ^a   Gray, Mark ^a   Lynch, Vincent M ^a   Sorey, Steven ^a   Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; COMPUTATIONAL COMPLEXITY; ESTERS; NUCLEAR MAGNETIC RESONANCE; SOLVENTS; X RAY CRYSTALLOGRAPHY;

ANALOGOUS BORONIC ACIDS; INTRAMOLECULAR N-B DATIVE BONDS; MOLECULAR RECOGNITION; STRUCTURAL INVESTIGATION;

BORON COMPOUNDS;

2 (PYRROLIDINYLMETHYL)PHENYLBORONIC ACID; AMMONIA; BORON; BORON 11; BORONIC ACID DERIVATIVE; CARBOHYDRATE; CARBOXYLIC ACID DERIVATIVE; CATECHOL; CATECHOLAMINE; CHLOROFORM; METHANOL; NITROGEN; PYRROLIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSOR; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

BORON; BORONIC ACIDS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITROGEN; PYRROLIDINES;

EID: 31944449355     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055817c     Document Type: Article

References (80)

1. Kuivila, H. G.; Keough, A. H.; Soboczenski, E. J. J. Org. Chem. 1954, 19, 780-783.
2. Dewar, M. J. S.; Kubba, V. P.; Pettit, R. J. Chem. Soc., Abstracts 1958, 3076-3079.
3. Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769-774.
4. Letsinger, R. L.; Hamilton, S. B. J. Org. Chem. 1960, 25, 592-595.
5. Jensen, K. A.; Pedersen, T. Acta Chem. Scand. 1961, 15, 1780-1781.
6. Letsinger, R. L.; MacLean, D. B. J. Am. Chem. Soc. 1963, 85, 2230-2236.
7. Kankare, J. J.; Varhiala, J. Anal. Chim. Acta 1978, 99, 151-156.
8. James, T. D.; Linnane, P.; Shinkai, S. Chem. Commun. 1996, 281-288.
9. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922.
10. Wang, W.; Gao, X.; Wang, B. Curr. Org. Chem. 2002, 6, 1285-1317.
11. Striegler, S. Curr. Org. Chem. 2003, 7, 81-102.
12. Fang, H.; Kaur, G.; Wang, B. J. Fluoresc. 2004, 14, 481-489.
13. Phillips, M. D.; James, T. D. J. Fluoresc. 2004, 14, 549-559.
14. Cao, H.; Heagy, M. D. J. Fluoresc. 2004, 14, 569-584.
15. Gray, C. W., Jr.; Houston, T. A. J. Org. Chem. 2002, 67, 5426-5428.
16. Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677.
17. Wiskur, S. L.; Lavigne, J. J.; Matzger, A.; Tobey, S. L.; Lynch, V. M.; Anslyn, E. V. Chem. Eur. J. 2004, 10, 3792-3804.
18. Nguyen, B. T.; Wiskur, S. L.; Anslyn, E. V. Org. Lett. 2004, 6, 2499- 2501.
19. Zhao, J.; Fyles, T. M.; James, T. D. Angew. Chem., Int. Ed. 2004, 43, 3461-3464.
20. Zhao, J.; Davidson, M. G.; Mahon, M. F.; Kociok-Kohn, G.; James, T. D. J. Am. Chem. Soc. 2004, 126, 16179-16186.
21. Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260-4269.
22. Yoon, J.; Czarnik, A. W. Bioorg. Med. Chem. 1993, 1, 267-271.
23. Secor, K. E.; Glass, T. E. Org. Lett. 2004, 6, 3727-3730.
24. Maue, M.; Schrader, T. Angew. Chem., Int. Ed. 2005, 44, 2265-2270.
25. Paugam, M.-F.; Valencia, L. S.; Boggess, B.; Smith, B. D. J. Am. Chem. Soc. 1994, 116, 11203-11204.
26. Paugam, M.-F.; Bien, J. T.; Smith, B. D.; Chrisstoffels, L. A. J.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1996, 118, 9820-9825.
27. Weith, H. L.; Wiebers, J. L.; Gilham, P. T. Biochemistry 1970, 9, 4396-4401.
28. Rosenberg, M.; Wiebers, J. L.; Gilham, P. T. Biochemistry 1972, 11, 3623-3628.
29. Barker, S. A.; Halt, B. W.; Somers, P. J.; Woodbury, R. R. Carbohydr. Res. 1973, 26, 55-64.
30. Reske, K.; Schott, H. Angew. Chem., Int. Ed. Engl. 1973, 12, 417-418.
31. Wulff, G.; Vesper, W. J. Chromatogr. 1978, 167, 171-186.
32. Glad, M.; Ohlson, S.; Hansson, L.; Mansson, M-O.; Mosbach, K. J. Chromatogr. 1980, 200, 254-260.
33. Wulff, G. Pure Appl. Chem. 1982, 54, 2093-2102.
34. Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812-1832.
35. Suri, J. T.; Cordes, D. B.; Capuccio, F. E.; Wessling, R. A.; Singaram, B. Angew. Chem., Int. Ed. 2003. 42, 5857-5859.
36. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Curr. Opin. Biotechnol. 2005, 16, 100-107.
37. Burgemeister, T.; Grobe-Einsler, R.; Grotstollen, R.; Mannschreck, A.; Wulff, G. Chem. Ber. 1981, 114, 3403-3411.
38. Wulff, G.; Lauer, M.; Bohnke, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 741-742.
39. Lauer, M.; Bohnke, H.; Grotstollen, R.; Salehnia, M.; Wulff, G. Chem. Ber. 1985, 118, 246-260.
40. Lauer, M.; Wulff, G. J. Chem. Soc., Perkin Trans. 2 1987, 745-749.
41. Bello-Ramirez, M. A.; Martinez, M. E. R.; Flores-Parra, A. Heteroat. Chem. 1993, 4, 613-620.
42. Nagai, Y.; Kobayashi, K.; Toi, H.; Aoyama, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2965-2971.
43. Norrild, J. C.; Eggert, H. J. Am. Chem. Soc. 1995, 117, 1479-1484.
44. Bielecki, M.; Eggert, H.; Norrild, J. C. J. Chem. Soc., Perkin Trans. 2 1999, 449-455.
45. Norrild, J. C. J. Chem. Soc., Perkin Trans. 2 2001, 719-726.
46. Norrild, J. C.; Søtofte, I. J. Chem. Soc., Perkin Trans. 2 2001, 727-732.
47. Wiskur, S. L.; Lavigne, J. J.; Ait-Haddou, H.; Lynch, V. M.; Chiu, Y. H.; Canary, J. W.; Anslyn, E. V. Org. Lett. 2001, 3, 1311-1314.
48. Otsuka, H.; Uchimura, E.; Koshino, H.; Okano, T.; Kataoka, K. J. Am. Chem. Soc. 2003, 125, 3493-3502.
49. Ni, W.; Kaur, G.; Springsteen, G.; Wang, B.; Franzen, S. Bioorg. Chem. 2004, 32, 571-581.
50. Bosch, L. I.; Fyles, T. M.; James, T. D. Tetrahedron 2004, 60, 11175-11190.
51. Paugam, M.-F.; Smith, B. D. Tetrahedron Lett. 1993, 34, 3723-3726.
52. Kubo, Y.; Kobayashi, A.; Ishida, T.; Misawa, Y.; James, T. D. Chem. Commun. 2005, 2846-2848.
53. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 477-478.
54. James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982-8987.
55. Franzen, S.; Ni, W.; Wang, B. J. Phys. Chem. B 2003, 107, 12942-12948.
56. Höpfl, H. J. Organomet. Chem. 1999, 581, 129-149.
57. Norrild, J. C.; Søtofte, I. J. Chem. Soc.. Perkin Trans. 2 2002, 303-311.
58. Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2003, 680, 257-262.
59. Bosch, L. I.; Mahon, M. F.; James, T. D. Tetrahedron Lett. 2004, 45, 2859- 2862.
60. Fournier, J.-H.; Maris, T.; Wuest, J. D.; Guo, W.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002-1006.
61. Toyota, S.; Oki, M. Bull. Chem. Soc. Jpn. 1992, 65, 1832-1840.
62. Toyota, S.; Futawaka, T.; Asakura, M.; Ikeda, H.; Oki, M. Organometallics 1998, 17, 4155-4163.
63. Braga, D.; Polito, M.; Bracaccini, M.; D'Addario, D.; Tagliavini, E.; Sturba, L. Organometallics 2003, 22, 2142-2150.
64. 3) spectra of fresh and aged samples. The aged sample can be restored with an azeotropic treatment.
65. Biedrzycki, M.; Scouten, W. H.; Biedrzycka, Z. J. Organomet. Chem. 1992, 431, 255-270.
66. Lauer, M.; Wulff, G. J. Organomet. Chem. 1983, 250, 1-9.
67. Brown, H. C.; Vara Prasad, J. V. N. J. Org. Chem. 1986, 51, 4526-4530.
68. Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472-1474.
69. Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1474-1476.
70. Reetz, M. T.; Niemeyer, C. M.; Hermes, M.; Goddard, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1017-1019.
71. Arimori, S.; Ward, C. J.; James, T. D. Chem. Commun. 2001, 2018-2019.
72. Zhong, S.; Jordan, F.; Kettner, C.; Polgar, L. J. Am. Chem. Soc. 1991, 113, 9429-9435.
73. Singhal, R. P.; Ramamurthy, B.; Govindraj, N.; Sarwar, Y. J. Chromatogr. 1991, 543, 17-38.
74. 3OD is assigned to the trimethyl ester of 4.
75. Van, J.; Springsteen, G.; Deeter, S.; Wang, B. Tetrahedron 2004, 60, 11205-11209.
76. James, T. D.; Shinkai, S. Top. Curr. Chem. 2001, 218, 159-200.
77. Springsteen, G.; Wang, B. Tetrahedron 2002, 58, 5291-5300.
78. Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874-5875.
79. Shabbir, S. H.; Anslyn, E. V., unpublished results.
80. 11B NMR spectra.