Solid-state 11B and 13C NMR, IR, and X-ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Magnetic Resonance in Chemistry

Volumn 50, Issue 5, 2012, Pages 388-401

  Oh, Se Woung ^a,c   Weiss, Joseph W E ^a,d   Kerneghan, Phillip A ^b   Korobkov, Ilia ^a   Maly, Kenneth E ^b   Bryce, David L ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b WILFRID LAURIER UNIVERSITY   (Canada)

^c Mokpo National University   (South Korea)

^d Bruker Corporation   (United States)

Author keywords

boron 11; boronate esters; boronic acids; carbon 13; chemical shift tensor; isotope effects; nuclear magnetic resonance; quadrupolar coupling constant; relaxation anisotropy; solid state NMR

Indexed keywords

BORON; CARBON; CHEMICAL SHIFT; COMPUTATION THEORY; ELECTRIC FIELDS; ESTERS; INFRARED SPECTROSCOPY; ISOTOPES; LIGHT POLARIZATION; MAGIC ANGLE SPINNING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; TENSORS; X RAY CRYSTALLOGRAPHY;

ARYLBORONIC ACIDS; BORON-11; BORONATE ESTERS; BORONIC ACID; CARBON-13; CHEMICAL SHIFT TENSORS; ISOTOPE EFFECT; QUADRUPOLAR COUPLING CONSTANTS; RELAXATION ANISOTROPY; SOLID STATE NMR;

DENSITY FUNCTIONAL THEORY;

BORONIC ACID DERIVATIVE; CATECHOL; CATECHOL DERIVATIVE; ESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BORONIC ACIDS; CATECHOLS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 84860348047     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.3815     Document Type: Article

References (48)

1. J. W. E. Weiss, D. L. Bryce,. J. Phys. Chem. A 2010, 114, 5119-5131.
2. D. G. Hall, Boronic Acids. Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, 2005.
3. C. Dai, Y. Cheng, J. Cui, B. Wang,. Molecules 2010, 15, 5768-5781.
4. W. Yang, X. Gao, B. Wang,. Med. Res. Rev. 2003, 23, 346-368.
5. K. E. Maly, N. Malek, J.-H. Fournier, P. Rodriguez-Cuamatzi, T. Maris, J. D. Wuest,. Pure Appl. Chem. 2006, 78, 1305-1321.
6. R. Nishiyabu, Y. Kubo, T. D. James, J. S. Fossey,. Chem. Commun. 2011, 47, 1124-1150.
7. N. Miyaura, A. Suzuki,. Chem. Rev. 1995, 95, 2457-2483.
8. A. Suzuki,. J. Organomet. Chem. 1999, 576, 147-168.
9. P. Pyykkö,. Mol. Phys. 2008, 106, 1965-1974.
10. N. S. Barrow, J. R. Yates, S. A. Feller, D. Holland, S. E. Ashbrook, P. Hodgkinson, S. P. Brown,. Phys. Chem. Chem. Phys. 2011, 13, 5778-5789.
11. A. Brinkmann, M. Edén,. Can. J. Chem. 2011, 89, 892-899.
12. D. L. Bryce, R. E. Wasylishen, M. Gee,. J. Phys. Chem. A 2001, 105, 3633-3640.
13. Ö. Alver, C. Parlak,. Vib. Spectrosc. 2010, 54, 1-9.
14. Ö. Alver,. C. R. Chimie 2011, 14, 446-455.
15. R. K. Harris, A. C. Olivieri,. Prog. Nucl. Magn. Reson. Spectrosc. 1992, 24, 435-456.
16. J. Mason,. Solid State Nucl. Magn. Reson. 1993, 2, 285-288.
17. H. R. Snyder, M. S. Konecky, W. J. Lennarz,. J. Am. Chem. Soc. 1958, 80, 3611-3615.
18. T. M. B. Islam, K. Yoshino, H. Nomura, T. Mizuno, A. Sasane,. Anal. Sci. 2002, 18, 363-366.
19. M. R. O'Donovan, C. D. Mee, S. Fenner, A. Teasdale, D. H. Phillips,. Mutat. Res. 2011, 724, 1-6.
20. W. T. Dixon, J. Schaefer, M. D. Sefcik, E. O. Stejskal, R. A. McKay,. J. Magn. Reson. 1982, 49, 341-345.
21. S. J. Opella, M. H. Frey,. J. Am. Chem. Soc. 1979, 101, 5854-5856.
22. S. Hayashi, K. Hayamizu,. Bull. Chem. Soc. Jpn. 1989, 62, 2429-2430.
23. E. L. Hahn,. Phys. Rev. 1950, 80, 580-594.
24. D. Freude, J. Haase,. NMR Basic Princ. Prog. 1993, 29, 1.
25. APEX Software Suite v.2010, Bruker AXS, Madison, WI, 2005.
26. G. M. Sheldrick,. Acta Crystallogr. A 2008, 64, 112-122.
27. D. Massiot, F. Fayon, M. Capron, I. King, S. Le Calvé, B. Alonso, J.-O. Durand, B. Bujoli, Z. Gan, G. Hoatson,. Magn. Reson. Chem. 2002, 40, 70-76.
28. K. Eichele, R. E. Wasylishen, WSOLIDS NMR Simulation Package, Version 1.17.30, Dalhousie University, Halifax, 2001.
29. D. W. Alderman, M. S. Solum, D. M. Grant,. J. Chem. Phys. 1986, 84, 3717-3725.
30. A. D. Becke,. J. Chem. Phys. 1993, 98, 5648-5652.
31. C. Lee, W. Yang, R. G. Parr,. Phys. Rev. B 1988, 37, 785-789.
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
33. M. D. Segall, P. J. D. Lindan, M. J. Probert, C. J. Pickard, P. J. Hasnip, S. J. Clark, M. C. Payne,. J. Phys. Condens. Matter 2002, 14, 2717-2744.
34. S. J. Clark, M. D. Segall, C. J. Pickard, P. J. Hasnip, M. I. J. Probert, K. Refson, M. C. Payne,. Z. Kristallogr. 2005, 220, 567-570.
35. H. J. Monkhorst, J. D. Pack,. Phys. Rev. B 1976, 13, 5188-5192.
36. M. C. Haberecht, M. Bolte, M. Wagner, H.-W. Lerner,. J. Chem. Crystallogr. 2005, 35, 657-664.
37. M. Kurt,. J. Raman Spectrosc. 2009, 40, 67-75.
38. D. W. Aubrey, M. F. Lappert, H. Pyszora,. J. Chem. Soc. 1961, 1931-1938.
39. Y. Erdogdu, M. T. Güllüoǧlu, M. Kurt,. J. Raman Spectrosc. 2009, 40, 1615-1629.
40. J. A. Faniran, H. F. Shurvell,. Can. J. Chem. 1968, 46, 2089-2095.
41. F. K. Butcher, W. Gerrard, M. Howarth, E. F. Mooney, H. A. Willis,. Spectrochim. Acta 1964, 20, 79-95.
42. S. Adiga, D. Aebi, D. L. Bryce,. Can. J. Chem. 2007, 85, 496-505.
43. M. Edén, L. Frydman,. J. Phys. Chem. B 2003, 107, 14598.
44. C. J. Jameson,. J. Chem. Phys. 1977, 66, 4983-4988.
45. C. J. Jameson, H. J. Osten,. Annu. Rep. Nucl. Magn. Reson. Spectrosc. 1986, 17, 1-78.
46. W. Gombler,. J. Am. Chem. Soc. 1982, 104, 6616.
47. C. J. Jameson, Encyclopedia of NMR, Wiley, Chichester, 1996.
48. K. Jackowski, W. Makulski, A. Szyprowska, A. Antušek, M. Jaszuński, J. Jusélius,. J. Chem. Phys. 2009, 130, 044309.