Charge-transfer interactions of metoclopramide nausea drug against six kind of π-acceptors: spectral and thermal discussions

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 5:123:455-66. doi: 10.1016/j.saa.2013.12.093. Epub 2014 Jan 2.

Abstract

The target of this paper is aimed to discuss the fast and newly techniques in order to assessment the metoclopramide (Mcp) nausea drug in pure form in solid and solution shape with different kind of π-acceptors upon charge transfer interactions. Charge-transfer complexes (CTC) of metoclopramide with picric acid (PA), 2,3-dichloro-5,6-dicyano-p-benzoquinon (DDQ), tetracyanoquinodimethane (TCNQ), m-dinitrobenzene (DNB), p-nitrobenzoic acid (p-NBA) and tetrachloro-p-quinon (p-CL) have been studied spectrophotometrically in absolute methanol at room temperature. The stoichiometries of the complexes were found to be 1:1 ratio by the spectrophotometric titration between metoclopramide and represented π-acceptors. The equilibrium constants, molar extinction coefficient (εCT) and spectroscopic-physical parameters (standard free energy (ΔG°), oscillator strength (ƒ), transition dipole moment (μ), resonance energy (RN) and ionization potential (ID)) of the complexes were determined upon the modified Benesi-Hildebrand equation. The results indicate that the formation constants for the complexes depend on the nature of electron acceptors and configuration of drug donor, and also the spectral studies of the complexes were determined by (infrared, Raman, and (1)H NMR) spectra and X-ray powder diffraction (XRD). The charge-transfer complexes are formed during the interaction of electron-acceptors and electron-donors as result of partial or complete transfer of a negative charge from (D(+)-A(-)).

Keywords: Charge-transfer complexes; Metoclopramide; Spectroscopic; π-Acceptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Antiemetics / chemistry*
  • Antiemetics / pharmacology
  • Bacteria / drug effects
  • Bacterial Infections / drug therapy
  • Fungi / drug effects
  • Magnetic Resonance Spectroscopy
  • Metoclopramide / chemistry*
  • Metoclopramide / pharmacology
  • Mycoses / drug therapy
  • Powder Diffraction
  • Spectroscopy, Fourier Transform Infrared
  • Thermodynamics
  • X-Ray Diffraction

Substances

  • Anti-Infective Agents
  • Antiemetics
  • Metoclopramide