Resonance Raman characterization of the different forms of ground-state 8-substituted 7-hydroxyquinoline caged acetate compounds in aqueous solutions

The Journal of Physical Chemistry. a
Huiying AnDavid Lee Phillips

Abstract

To investigate the substituent effect on the distribution of the forms of the ground-state species of 8-substituted 7-hydroxyquinolines, ultraviolet-absorption and resonance Raman experiments were performed for 8-chloro-7-hydroxyquinoline (CHQ-OAc) and 8-cyano-7-hydroxyquinoline (CyHQ-OAc) in acetonitrile (MeCN), in NaOH-H(2)O/MeCN (60:40, v/v, pH 11-12), and in H(2)O/MeCN (60:40, v/v, pH 6-7) solutions, and these results were compared to those previously reported for the 8-bromo-7-hydroxyquinoline (BHQ-OAc) compound. Swapping a bromine atom in BHQ-OAc for a chlorine atom in CHQ-OAc causes the amount of the tautomeric species to become larger, although the neutral species is still the predominant species for both systems in water-rich solutions. The absorption spectra and the resonance Raman spectra of CyHQ-OAc suggest that, because of the strong electron-withdrawing nature of the cyano substituent, a measurable amount of the anionic species is present and the tautomeric species cannot be easily detected in water-rich solutions. The results reported here reveal large substituent effects on the distribution of the different forms of the XHQ-OAc compounds in largely aqueous solutions. The steric effect of the 8-substituted group ...Continue Reading

References

Jul 18, 2001·Journal of the American Chemical Society·P ZhuD L Phillips
Jun 9, 2005·Journal of the American Chemical Society·Pik Ying ChanDavid Lee Phillips
Mar 30, 2006·Journal of the American Chemical Society·Yue ZhuTimothy M Dore
Jun 28, 2006·The Journal of Physical Chemistry. B·Oh-Hoon KwonDu-Jeon Jang
Jul 21, 2006·The Journal of Physical Chemistry. B·Han Jung ParkDu-Jeon Jang
Feb 3, 2007·The Journal of Physical Chemistry. a·Jiadan XueDavid Lee Phillips

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Citations

Feb 2, 2017·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jinqing HuangTimothy M Dore
Aug 15, 2017·Journal of the American Chemical Society·Naeem AsadTimothy M Dore

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