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AuthorBani-Yaseen, Abdulilah Dawoud
AuthorAl-Balawi, Mona
Available date2016-02-22T09:04:54Z
Publication Date2014-06
Publication NamePhysical Chemistry Chemical Physics
ResourceScopus
CitationBani-Yaseen, A.D., Al-Balawi, M. "The solvatochromic, spectral, and geometrical properties of nifenazone: A DFT/TD-DFT and experimental study", (2014) Physical Chemistry Chemical Physics, 16 (29), pp. 15519-15526.
ISSN1463-9076
URIhttp://dx.doi.org/10.1039/c4cp01679c
URIhttp://hdl.handle.net/10576/4174
AbstractThe solvatochromic, spectral, and geometrical properties of nifenazone (NIF), a pyrazole-nicotinamide drug, were experimentally and computationally investigated in several neat solvents and in hydro-organic binary systems such as water-acetonitrile and water-dioxane systems. The bathochromic spectral shift observed in NIF absorption spectra when reducing the polarity of the solvent was correlated with the orientation polarizability (?f). Unlike aprotic solvents, a satisfactory correlation between ?max and ?f was determined (linear correlation of regression coefficient, R, equal to 0.93) for polar protic solvents. In addition, the medium-dependent spectral properties were correlated with the Kamlet-Taft solvatochromic parameters (?, ?, and ?*) by applying a multiple linear regression analysis (MLRA). The results obtained from this analysis were then employed to establish MLRA relationships for NIF in order to estimate the spectral shift in different solvents, which in turn exhibited excellent correlation (R > 0.99) with the experimental values of ?max. Density functional theory (DFT) and time-dependent DFT theory calculations coupled with the integral equation formalism-polarizable continuum model (IEF-PCM) were performed to investigate the solvent-dependent spectral and geometrical properties of NIF. The calculations showed good and poor agreements with the experimental results using the CAM-B3LYP and B3LYP functionals, respectively. Experimental and theoretical results confirmed that the chemical properties of NIF are strongly dependent on the polarity of the chosen medium and its hydrogen bonding capability. This in turn supports the hypothesis of the delocalization of the electron density within the pyrazole ring of NIF.
Languageen
PublisherRoyal Society of Chemistry
SubjectAcetonitriles
Anti-Inflammatory Agents, Non-Steroidal
Antipyrine
Dioxanes
Hydrogen Bonding
Niacinamide
Quantum Theory
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
TitleThe solvatochromic, spectral, and geometrical properties of nifenazone: A DFT/TD-DFT and experimental study
TypeArticle
Pagination15519-15526
Issue Number29
Volume Number16
dc.accessType Abstract Only


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