Communication of electronic information over nanometer distances with supramolecular transduction. An experimental and density functional investigation

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 2000, Pages 1309-1313

  Deans, Robert ^a   Cuello, Alejandro O ^a   Galow, Trent H ^a   Ober, Matthias ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ASSOCIATION REACTIONS; CHLORINE COMPOUNDS; COMPLEXATION; ELECTRONIC PROPERTIES; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTASSIUM COMPOUNDS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL); TITRATION;

CONJUGATED DIAMINOTRIAZINE-FUNCTIONALIZED RECEPTOR; DICYANDIAMIDE; DIMERIZATION ISOTHERMS; ISOBUTYRYL CHLORIDE; POTASSIUM CHLORIDE;

MOLECULAR DYNAMICS;

EID: 0034236746     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909634e     Document Type: Article

References (28)

1. (a) A. Fersht, Enzyme Structure and Mechanism, 2nd edn., Freeman, New York, 1985
2. (b) G. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer Verlag, Berlin, 1991.
3. For recent biomimetic model systems see: (a) E. A. Gallo and S. H. Gellman, J. Am. Chem. Soc., 1993, 115, 9774
4. (b) J. S. Nowick, J. S. Chen and G. Noronha, J. Am. Chem. Soc., 1993, 115, 7636
5. (c) S. C. Zimmerman and T. J. Murray, Tetrahedron Lett., 1994, 35, 4077
6. (d) A. D. Hamilton, N. Pant and A. Muehldorf, Pure Appl. Chem., 1988, 60, 533
7. (e) A. Aggeli, M. Bell, N. Boden, J. N. Keen, P. F. Knowles, T. C. B. McLeish, M. Pitkeathly and S. E. Radford, Nature, 1997, 386, 259.
8. For overviews of sensor/devices see: (a) J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1988, 27, 89
9. (b) D. Goldhaber-Gordon, M. S. Montemerlo, J. C. Love, G. J. Opiteck and J. C. Ellenbogen, Proc. IEEE, 1997, 85, 521
10. (c) A. Aviram, J. Am. Chem. Soc., 1988, 110, 5687.
11. For further examples of flavin binding receptors see: (a) E. Breinlinger and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 1165
12. K. A. Connors, Binding Constants. The Measurement of Molecular Complex Stability, Wiley and Sons, New York, 1987.
13. dim, the dimerization constant.
14. HG, the chemical shift of the host-guest complex.
15. For purely electrostatic approach to predicting hydrogen bonding see: C. S. Wilcox, E. Kim, D. Romano, L. H. Kuo, A. L. Burt and D. P. Curran, Tetrahedron, 1995, 51, 621.
16. O. Exner, Correlation Analysis of Chemical Data, Plenum, New York, 1988.
17. For discussions and considerations on molecular calculations related to hydrogen bonds see, for example: (a) M. S. Gordon and J. H. Jensen, Acc. Chem. Res., 1996, 29, 536
18. (b) D. A. Smith, Modeling the Hydrogen Bond, ACS Symposium Series, ACS, Washington D.C., 1994
19. (c) S. Scheiner, Hydrogen Bonding: A Theoretical Perspective, Oxford University Press, New York, 1997
20. (d) K. Kim and R. A. Friesner, J. Am. Chem. Soc., 1997, 119, 12952.
21. (a) W. Khon and L. J. Sham, Phys. Rev., 1965, 140, A1133
22. (b) R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989
23. (c) J. P. Perdew and W. Yang, Phys. Rev., 1992, B 45, 1324
24. (d) J. K. Labanowsky, Density Functional Theory Methods in Chemistry, Springer-Verlag, New York, 1991.
25. A. Niemz and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 6833.
26. (1e + 3 → 1e.3), since both complexes under study are quite similar with only minor structural differences. The small discrepancy between the calculated and experimental energetics can be attributed to lack of solvent correction in the computational model.
27. Gaussian 94, Revision E.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
28. Spartan Version 4.1.2, Wavefunc Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715.