Solvent effects on chemical processes. 2. Binding constants of methyl orange with .alpha.-cyclodextrin in binary aqueous-organic solvents

Connors, Kenneth A.; Mulski, Michael J.; Paulson, Andrea

doi:10.1021/jo00032a036

Cited by 45 publications

(21 citation statements)

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“…These azobenzene substrates are "threaded" through the R-CyD cavity, 22 and completely fill it, hence -∆A ) 125. This argument is supported by our experimental solvent effect studies on Methyl Orange, 9,23 which yielded the parameter -g∆A ) 56, corresponding to -∆A ) 133; the cavity is filled with nonpolar guest substance.…”

Section: Resultsmentioning

confidence: 55%

Prediction of Binding Constants of α-Cyclodextrin Complexes

Connors¹

1996

Journal of Pharmaceutical Sciences

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Proceeding from a phenomenological theory of pairwise interactions (solvent-solvent, solvent-solute, and solute-solute), the binding constant K11 (in M-1) for 1:1 complex formation by alpha-cyclodextrin at a substrate binding site, at 25 degrees C in water, is given by log K11 = -1.74 - [Z] + 0.032(-delta A), where [Z] incorporates solvent-solute (solvation) and solute-solute interactions and delta A is the decrease in nonpolar surface area (in A2 molecule-1) on the substrate that is exposed to solvent when the binding site enters the cyclodextrin cavity. delta A is estimated from the structure of the binding site. Three levels of approximation are described for estimating [Z]. At the third (highest) level, the procedure when applied to 569 complex systems generated predicted values of log K11 that agreed within 0.30 unit of the experimental values in 58% of cases, and that agreed within 1.00 unit in 95% of cases.

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Section: Resultsmentioning

confidence: 55%

Prediction of Binding Constants of α-Cyclodextrin Complexes

Connors¹

1996

Journal of Pharmaceutical Sciences

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“…The spectral data collected in water with dye 2 were analyzed according to the method described by Connors [25,29] with Equation (1),…”

Section: Measurements Of Binding Constantsmentioning

confidence: 99%

“…[6,10] These dyes have been used in recent years in several studies related to solvatochromism, [6,7,9,10] halochromism, [11][12][13] mixed solvents, [14][15][16][17][18][19] and microheterogeneity in solution. [20] Despite the number of studies on the behavior in solution of some classes of dyes in the presence of CyDs, [2,[21][22][23][24][25] we can find very few similar studies related to solvatochromic dyes, for instance, with the well-known probes 1 and 2. Recently, a study of the effect of the addition of methyl-b-CyD on the solvatochromic bands of 1 and 2, using the UV-Vis technique and several media, showed that the dyes interact strongly with CyD by means of hydrogen bonding and hydrophobic effects.…”

Section: Introductionmentioning

confidence: 99%

Interaction of Cyclodextrins with Brooker's Merocyanine in Aqueous Solution

Nicolini

Venturini

Andreaus

et al. 2008

Spectroscopy Letters

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The UV-Vis spectroscopic behavior of the solvatochromic dye 4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadien-1-one (Brooker's merocyanine) was investigated in aqueous solution (pH 10.55) in the presence of increasing amounts of native (a-and b-) and modified (methyl-b-and hydroxypropyl-b-) cyclodextrins. The data obtained showed that a bathochromic shift occurs in the dye solution after the addition of the cyclodextrins, indicating that the probe is transferred to a low-polarity microenvironment with the addition of the cyclodextrin. Experimental data also suggest the occurrence of a 1:1 dye:cyclodextrin inclusion complex.

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“…[22] The influence of a binary solvent medium on the association constants for binding of a guest by b-CD has been studied by Connors et al, who dissected the free energy change for complex formation in contributions stemming from solvent ± solvent interactions (the general medium effect), solvent ± solute interactions (the solvation effect), and solute ± solute interactions (the intersolute effect). [23] In order to find the association constant for the binding of the bisadamantane guest by the CD dimer in 100 % water, an extrapolation of the binding constants observed in the methanol/water mixtures is needed. Of the three factors described by Connors et al, the part describing the solvent ± solvent interactions can be used as is, since in both cases a methanol/water system is studied.…”

Section: Resultsmentioning

confidence: 99%

Complexation and (Templated) Synthesis of Rhenium Complexes with Cyclodextrins and Cyclodextrin Dimers in Water

et al. 2001

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Several small, lipophilic rhenium complexes form inclusion complexes with native beta-cyclodextrin (beta-CD) and beta-CD dimers. Association constants larger than 10(9)M(-1) were obtained using dimers. The use of beta-CD also enabled the synthesis of these rhenium complexes in water, in excellent yields, through complexation of the otherwise insoluble corresponding ligands. The influence of the reaction time and temperature on the configuration of the reaction products has been investigated in depth for one of these complexes. Using a beta-CD dimer, it proved possible to specifically template the formation of one configuration. The strength of the complexes of the rhenium complexes in cyclodextrin dimers may allow radiolabeling of biomolecules.

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Solvent effects on chemical processes. 2. Binding constants of methyl orange with .alpha.-cyclodextrin in binary aqueous-organic solvents

Cited by 45 publications

References 0 publications

Prediction of Binding Constants of α-Cyclodextrin Complexes

Prediction of Binding Constants of α-Cyclodextrin Complexes

Interaction of Cyclodextrins with Brooker's Merocyanine in Aqueous Solution

Complexation and (Templated) Synthesis of Rhenium Complexes with Cyclodextrins and Cyclodextrin Dimers in Water

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