Role of Intermolecular Hydrogen Bonding in Some Supramolecules: An AMI Study of the Binding Energies and Hyperpolarizabilities

Chemistry of Materials

Volumn 7, Issue 10, 1995, Pages 1843-1848

  Sarma, J A R P ^a   Laxmikanth Rao, J ^a   Bhanuprakash, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

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Indexed keywords

EID: 0000604570     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm00058a014     Document Type: Article

References (43)

1. IICT Communication No. 3512.
2. Lehn, J.-M. Angew Chem., Int. Ed. Engl. 1990, 29, 1304.
3. Etter, M. C.; Frankenbach, G. M.; Adsmond, D. A. Mol. Cryst. Liq. Cryst. 1990, 187, 25.
4. Kollman, P. A.; Allen, L. C. Chem. Rev. 1972, 72, 283.
5. Fan, E.; Vicent, C.; Geib, S. J.; Hamilton, A. D. Chem. Mater. 1994, 6, 1113.
6. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
7. MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. Hydrogen Bonding in Biological Structures Jeffrey, G. A., Saenger, W., Eds.; Springer-Verlag: Berlin, 1991.
8. Toledo, L. M.; Lauher, J. W.; Fowler, F. W. Chem. Mater. 1994, 8, 1222.
9. Sarma, J. A. R. P.; Dhurjati, M. S. K.; Bhanuprakash, K.; Ravikumar, K. J. Chem. Soc., Chem. Commun. 1993, 440.
10. Aoyama, Y. In Supramolecular Chemistry, Balzani, V., De Cola, L., Eds.; Kluwer Academic: Netherlands, 1992.
11. Etter, M. C. J. Phys. Chem. 1991, 95, 4601.
12. Sharma, C. V. K. M.; Panneerselvam, K.; Pilati, T.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1993, 2209.
13. Frankenbach, G. M.; Etter, M. C. Chem. Mater. 1992, 4, 272.
14. Etter, M. C.; Huang, K. S. Chem. Mater. 1992, 4, 824.
15. Sarma, J. A. R. P.; Dhuijati, M. S. K.; Ravikumar, K.; Bhanuprakash, K. Chem. Mater. 1994, 6, 1369.
16. Andre, J. M.; Delhalle, J. Chem. Rev. 1991, 91, 843.
17. Waite, J.; Papadopulos, G. Chem. Phys. Lett. 1985,114, 539.
18. Kecki, Z.; Sadley, J.; Sadley, A. J. J. Mol. Struct. (THEOCHEM) 1982, 5, 71.
19. Yasukawa, T.; Kimura, T.; Uda, M. Chem. Phys. Lett. 1990, 169, 259.
20. Jasien, P. J.; Fitzgerald, G. J. Chem. Phys. 1990, 93, 2554.
21. Perez, J.; Dupuis, M. J. Phys. Chem. 1991, 95, 6525.
22. Zyss, J.; Berthier, S. J. Chem. Phys. 1982, 77, 3635.
23. Dirk, C. W.; Twieg, R. J.; Wagniere, G. J. Am. Chem. Soc. 1986, 108, 5387.
24. Milleflori, S.; Alparone, A. J. Chem. Soc., Faraday Trans. 1994, 90, 2873.
25. Sarma, J. A. R. P.; Desiraju, G. R. J. Am. Chem. Soc. 1986, 108, 2791.
26. Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222.
27. Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1987, 1187.
28. Dannenberg, J. J. Chem. Mater. 1990, 2, 635.
29. Vinson, L. K.; Dannenberg, J. J. J. Am. Chem. Soc. 1989, 111, 2777.
30. Dannenberg, J. J.; Evleth, E. M. Int. J. Quantum Chem. 1992, 44, 869.
31. Laszlo, T.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197.
32. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
33. Sharma, C. V. K. M.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2345.
34. Locally modified version of the program MOPAC 4.0.
35. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
36. Kurtz, H. A.; Stewart, J. J. P.; Dieter, K. M. J. Comput. Chem. 1990, 11, 82.
37. Still, C. MACROMODEL, A Molecular Modelling Program, Version 2.5; Columbia University: New York, 1987.
38. Crystal structural data of some acids, amide dimers, and other dimers considered was retrieved from Cambride Structural Database. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T., Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. S. Rodgers, J. R.; Watson, D. G. Acta Crystallogr., Sect. B 1979, 35, 2331.
39. Williams, D. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 690. Nonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. Z., Zyss, J., Eds.; Academic Press: Orlando, FL, 1987; Vol. 1 and 2.
40. In the absence of any constraint, some of the acid and amide dimers optimized to highly nonplanar, twisted, and nonacceptable conformations; however, both nitro dimers are well behaved. To make sure that a similar planar conformation is maintained in all four dimers, constraint in the dihedral angle was applied in all. While calculating the HBE, values of molecules with similar constraints were considered.
41. The maximum deviation of nitrogen from the plane of three connected atoms is only ~0.12 Å, whereas for complete pyramidality, according to sp3 type bonding, is ~0.34 Å. Also, no significant deviation in β; and γ are observed between the pyramidal and planar conformations.
42. The strength of the donors and acceptors are baaed on the Hammett constants, σ values and are from: Hansch, C., Leo, A.; Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979.
43. Matsuzawa, N.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6232.