The Protonation and Hydrogen Bonding Interaction in N,N-dimethyl-4-(phenylimino-methyl)-aniline System

Tong-Ing Ho; Tai-Chen Lee; Jinn-Hsuan Ho; Shun-Li Wang

doi:10.6180/jase.2003.6.1.05

The Protonation and Hydrogen Bonding Interaction in N,N-dimethyl-4-(phenylimino-methyl)-aniline System

Tong-Ing Ho This email address is being protected from spambots. You need JavaScript enabled to view it.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.