Study and comparison of Equilibrium vs. resonance in keto-enol tautomerization in some piroxicam derivatives

Subject Areas :

abolghasem shameli ¹ , Ebrahim balali ² , sara hallajian ³ , behrooz yousefzadeh ⁴

1 - departman of chemistry, university branch omidiyeh, omidiyeh, iran
2 - Department of Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran
3 - Department of Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran
4 - Department of Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran

Received: 2017-03-06 Accepted : 2017-09-13 Published : 2017-08-23

Keywords: piroxicam, imine, enol, Tautomer,

Abstract :

The Piroxicam derivatives are nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and help relieve symptoms of arthritis. Which has two or more forms are tautomers, That both form tautomers due to the flexible structure and the possibility of turning around bonding C-C, C-O, C-N and C-S. The hydrogen-bond also play a very important roles in structure compound because Intramolecular and intermolecular hydrogen bond in which the different. In this study, theoretical and computational accuracy using BPV860 / 6-311G ** in the gas phase with software Gaussian 03. Infrared Spectroscopic and Theoretical Studies on the derivetives piroxicam. Relationship between the structure and the stability of these enols was discussed. That enol- keto or imine- enamine forms easily converted into stable forms