Femtosecond dynamics of piroxicam structures in solutions

The Journal of Physical Chemistry. a
Michał Gil, Abderrazzak Douhal

Abstract

We report on studies of femtosecond dynamics of a nonsteroidal anti-inflammatory drug, piroxicam (1), in water at three different pHs and for comparison in two aprotic solvents. An ultrafast excited-state proton-transfer (ESIPT) process takes place in neutral and cationic enol-type structures. Femtosecond emission and transient absorption experiments show that this reaction is barrierless, and the proton-transferred keto tautomer is formed in less than 100 fs in both organic solvents and acidic water. In neutral and alkaline water, the ESIPT is not present because of the prevalence of the anion structures at the ground state. For the excited anions (pH = 7, 11) and formed keto cations (pH approximately 3), an intramolecular charge-transfer process takes place in times shorter than 0.3 ps. The formed structures have a fluorescence lifetime of approximately 2-5 ps, depending on pH. In contrast, the internal twisting motion in organic solvents is slower (approximately 0.5-1 ps) and gives rotamers with lifetimes of tens of picoseconds. These results clearly show strong interactions of 1 with water, significantly distinct from those present in organic aprotic solvents. We believe that the results are important for a better understan...Continue Reading

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Citations

Mar 19, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Rajib Ghosh, Dipak K Palit
May 16, 2018·Physical Chemistry Chemical Physics : PCCP·Maria Rosaria di NunzioAbderrazzak Douhal
Oct 16, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Lorenzo AngioliniAbderrazzak Douhal
Sep 16, 2010·Chemistry : a European Journal·Elena Pérez-MayoralJiří Cejka
Sep 3, 2010·The Journal of Physical Chemistry. B·Boiko CohenAbderrazzak Douhal
Jul 26, 2014·The Journal of Physical Chemistry. B·Abderrazzak DouhalBoiko Cohen
Jun 21, 2012·The Journal of Physical Chemistry. B·Maria Rosaria di NunzioAbderrazzak Douhal
Nov 4, 2011·The Journal of Physical Chemistry. a·Sofia Kouras-HadefClaire Richard
Oct 11, 2011·The Journal of Physical Chemistry. B·Marco Franco-PérezRodolfo Gómez-Balderas
Mar 8, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Cristina MartínAbderrazzak Douhal
May 4, 2011·The Journal of Physical Chemistry. a·Maria Rosaria di NunzioAbderrazzak Douhal
Apr 30, 2014·The Journal of Physical Chemistry. B·Cristina MartinAbderrazzak Douhal

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