Boronic acids as molecular sensors NBO analysis and 13C chemical shifts as tools for evaluation of DFT geometry optimization of complexes of diphenylmethane 3,3′-diboronic acids and glucose

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1741-1748

  Uggla, Rolf ^a   Sundberg, Markku R ^a   Nevalainen, Vesa ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; GLUCOSE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MEMBRANE TRANSPORT; ENZYME INACTIVATION; ISOMERISM; PRIORITY JOURNAL; SENSOR;

EID: 0029920179     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00208-X     Document Type: Article

References (14)

1. Riggs, J. A.; Litchfield, R. K.; Smith, B. D. J. Org. Chem. 1996, 61, 1148.
2. (a) James, T. D.; Sandanayake, K. R. A. S., Shinkai, S. Nature 1995, 374, 345;
3. (b) Suenaga, H.; Mikami, M.; Sandanayake, S.; Shinkai, S. Tetrahedron Lett. 1995, 36, 4825;
4. (c) Norrild, J. Chr.; Eggert, H. J. Am. Chem. Soc. 1995, 117, 1479;
5. (d) Tsukagoshi, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4089.
6. Imada, T.; Kijima, H.; Takeuchi, M.; Shinkai, S. Tetrahedron 1996, 52, 2817.
7. DFT calculations: (a) Dmol, User Guide, Version 2.2, Biosym Technologies, San Diego, CA, March 1992;
8. (b) Dmol, User Guide, Version 2.3, Biosym Technologies, San Diego, CA, March 1993;
9. (c) Ziegler, T., Chem. Rev. 1991, 91, 651-667;
10. (d) Llamas-Saiz, A. L.; Foces-Foces, C.; Mo, O.; Yanez, M.; Elguero, E.; Elguero, J. J. Comput. Chem., 1995, 16, 263-272;
11. Generation of the models: (e) Initial structure of 2 generated using Chem3D Plus (Cambridge Scientific Computing, Inc., Cambridge, Mass.).
12. Gaussian 94, Revision B.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1995.
13. 13C chemical shifts we did not reoptimize the structure of 2 (optimized at the DN level using DMol) using Gaussian. Therefore, results related to the NBO analysis and determination of the chemical shifts could be considered only as estimates.
14. Determined on the basis of bond angles of the boron atoms as described in the literature (e.g. Nevalainen, V.; Uggla, R.; Sundberg, M. Tetrahedron: Asymm. 1995, 6, 1431).