19329-94-3Relevant academic research and scientific papers
Understanding Solvation: Comparison of Reichardt's Solvatochromic Probe and Related Molecular "core" Structures
Pires, Paulo A. R.,El Seoud, Omar A.,Machado, Vanderlei G.,De Jesus, Jéssica C.,De Melo, Carlos E. A.,Buske, Jonatan L. O.,Cardozo, Amanda P.
, p. 2213 - 2220 (2019)
The compound 2,6-diphenyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate, p-RB, shows distinct colors in different solvents (solvatochromism). The compound 4-(pyridinium-1-yl)phenolate, p-CB, represents the part of p-RB which is responsible for this phenomenon. We compared the solvatochromism of both compounds and also the structurally related 2-(pyridinium-1-yl)phenolate, o-CB, and (2,4-dimethyl-6-(2,4,6-triphenyl-N-pyridinium-1-yl)phenolate, o-RB. In pure solvents, plots of the empirical solvent polarity parameter [ET(probe), kcal/mol] of the different probes correlate linearly with slopes close to unity. That is, these probes are similarly sensitive to specific and nonspecific interactions with the solvents. The solvatochromism of p-CB and o-CB was studied, for the first time, in binary mixtures of water with dimethyl sulfoxide (DMSO) and 1-propanol (1-PrOH). The dependence of ET(probe) on mixture composition was nonideal due to preferential solvation of the probe by one component of the binary solvent mixture. We treated our solvatochromic data using a solvent-exchange model that considers formation of the complex solvents [HOH···O=S(CH3)2] and [HOH···O(H)-C3H7]. The model applies satisfactorily to our data and shows the importance to solvation of hydrogen-bonding and hydrophobic interactions. The preferential solvation of (more hydrophobic) p-RB is more pronounced than that of p-CB or o-CB. The solvent complex [OH2···O(H)-C3H7] is more efficient than [OH2···O=S(CH3)2] because of more possibilities of hydrogen bonding.
The solvatochromic behaviour of 2- and 4-pyridiniophenoxides
Gonzalez, Danilo,Neilands, Ojars,Rezende, Marcos Caroli
, p. 713 - 717 (2007/10/03)
The solvatochromic shifts of the two isomeric title betaines 4 and 5, built up from the unsubstituted pyridinio acceptor and phenoxide donor fragments, were recorded in twelve solvents and the data compared with results from semi-empirical (AM1) and ab initio (HF/6-311G and B3LYP/6-311G) calculations.
