Tong-Ing Ho 1 , Tai-Chen Lee1, Jinn-Hsuan Ho1 and Shun-Li Wang2
1Department of Chemistry National Taiwan University Taipei, Taiwan 106, R.O.C.
2Department of Chemistry National Chiayi University Chiayi, Taiwan 600, R.O.C.
Received:
December 24, 2002
Accepted:
February 10, 2003
Publication Date:
March 1, 2003
Download Citation:
||https://doi.org/10.6180/jase.2003.6.1.05
ABSTRACT
The influence of hydrogen bonding (HB) and protonation on an intramolecular charge transfer (ICT) compound, such as N,N-dimethyl-4-(phenylimino-methyl)-aniline (NMe2-4PmA) in the ground and excited state with two protic solvents 2,2,2-trifluoroethanol (TFE) and 2,2,2-trichloroethanol (TCE) is investigated. Mono HB and mono protonation complexes with TFE and TCE both in the ground state as well as in the excited state are all identified. TCE shows stronger protonation as well as hydrogen bonding ability in the ground state of NMe2-4PmA. In the excited state both TCE and TFE show similar behavior in the hydrogen bonding and protonation ability.
Keywords:
Hydrogen Bonding, Intramolecular Charge Transfer (ICT), Protonation
REFERENCES
- [1] Wang, S. L.; Ho, T. I.; Spectrochim. Acta A 2001, 57, 361.
- [2] Wang, S. L.; Ho, T. I.; Chem. Phys. Lett. 1997, 268, 434.
- [3] Wang, S. L.; Lee, T. C.; Ho, T. I. J. Photochem. Photobiol. A: Chem. 2002, 151, 21.
- [4] Wang, S. L.; Ho, T. I.; J. Photochem. Photobiol. A: Chem. 2000, 135, 119.
- [5] Kamlet, M. J.; Abbound, J. L. M.; Abrahan, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877.
- [6] Catalan, J.; Couto, A.; Gomez, J.; Saiz., J. L.; Laynez, J.; J. Chem. Soc., Perkin Tran. 1992, 2, 1181.
- [7] El-Bayoumi, M. A.; El-Asser, M.; Abdel-Halim, F. J. Am. Chem. Soc. 1971, 93, 586.
- [8] El-Bayoumi, M. A.; El-Asser, M.; Abdel-Halim, F. J. Am. Chem. Soc. 1971, 93, 590.
- [9] Abboud, J. L. M.; Sraidi, K.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1990, 55, 2230.
- [10] Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Taft, R. W.; Morris, J. J.; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J. L. M.; Sraidi, K.; Guiheneuf, G. J. Am. Chem. Soc. 1988, 110, 8543.
- [11] Molina, M. T.; Bouab, W.; Esseffar, M.; Herreros, M.; Notario, R.; Abboud, J. L. M.; Mo, O.; Yanez, M.; J. Org. Chem. 1996, 61, 5485.
- [12] Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Prekin Trans. 1989, 2, 699.
- [13] Kolling, O. W. J. Phys. Chem. 1992, 96, 1729.
- [14] Wang, S. L.; Ho, T. I.; Spectrochim. Acta A 2001, 57, 361.
- [15] Wang, S. L.; Ho, T. I.; Chem. Phys. Lett. 1997, 268, 434.
- [16] Wang, S. L.; Lee, T. C.; Ho, T. I. J. Photochem. Photobiol. A: Chem. 2002, 151, 21.
- [17] Wang, S. L.; Ho, T. I.; J. Photochem. Photobiol. A: Chem. 2000, 135, 119.
- [18] Kamlet, M. J.; Abbound, J. L. M.; Abrahan, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877.
- [19] Catalan, J.; Couto, A.; Gomez, J.; Saiz., J. L.; Laynez, J.; J. Chem. Soc., Perkin Tran. 1992, 2, 1181.
- [20] El-Bayoumi, M. A.; El-Asser, M.; Abdel-Halim, F. J. Am. Chem. Soc. 1971, 93, 586.
- [21] El-Bayoumi, M. A.; El-Asser, M.; Abdel-Halim, F. J. Am. Chem. Soc. 1971, 93, 590.
- [22] Abboud, J. L. M.; Sraidi, K.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1990, 55, 2230.
- [23] Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Taft, R. W.; Morris, J. J.; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J. L. M.; Sraidi, K.; Guiheneuf, G. J. Am. Chem. Soc. 1988, 110, 8543.
- [24] Molina, M. T.; Bouab, W.; Esseffar, M.; Herreros, M.; Notario, R.; Abboud, J. L. M.; Mo, O.; Yanez, M.; J. Org. Chem. 1996, 61, 5485.
- [25] Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Prekin Trans. 1989, 2, 699.
- [26] Kolling, O. W. J. Phys. Chem. 1992, 96, 1729.