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Light Scattering in Non-aqueous Solutions of Low-Molecular-Mass Compounds: Application for Supramer Analysis of Reaction Solutions

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Abstract

The use of static and dynamic light scattering (SLS and DLS, respectively) for chraracterization of solutions (0.005–0.20 mol·L− 1) of a series of carbohydrate-based low-molecular-mass compounds (glycosyl donors for chemical glycosylation) in anhydrous acetonitrile is described. The DLS data obtained suggest that, in the cases studied, the solute molecules form different supramolecular assemblies (supramers) with variable hydrodynamic radii. Analysis of concentration dependences of complementary SLS data for these solutions revealed that solvent quality may change dramatically with concentration and with the nature of solute. These results suggest that a combination of SLS and DLS is a valuable analytical tool for the supramer analysis of reaction solutions, which is useful for the rational selection of optimal concentrations for performing glycosylation reactions.

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Notes

  1. For the detailed discussion of the foundations of the supramer approach and supramer analysis of solutions (vide infra) as well as the relevant references not cited here see [29, 35].

  2. Polarimetry is extremely sensitive to changes in solution structure (see [24, 29, 46] for the detailed discussion).

  3. The use of light scattering could allow an extension of the suprmer analysis to solutions of achiral solutes.

  4. For the purpose of supramer analysis, it is not critical whether the Rh values represent the “true” dimensions of light scattering particles or just give us some response function that reflects the situation in the solution in a complex way.

  5. Note that only positive values of monotonically decreasing correlation function g1(τ) = g2(τ) – 1 can be correctly recalculated to hydrodynamic radii Rh values of “particles” dispersed in solvent. For this reason, only relatively small lag times (τ < 0.01 ms), at which correlation function is monotonically decreasing and assumes only positive values (until it becomes equal to zero), were considered for calculation of Rh values. The larger lag times cannot be considered for correct calculation of Rh values since the correlation function was increasing from zero before becoming positive. Therefore, at these greater lag times the correlation function can be considered as sign-alternating function, which is indicative of refractive index homogeneity of the medium and which corresponds to a structurally uniform solution.

  6. For solutions of compound 2 the negative slope for dilute solutions is also visible athough less clearly due to more considerable intensity scatter (see Fig. 4b).

  7. Note that compound 2 has additionally a different anomeric configuration, which changes the orientation of hydrogen bond accepting methoxycarbonyl group from equatorial (in 1 and 3) to axial (in 2). For this reason, a direct comparative analysis of SLS/DLS data for solutions of compound 2 with data for solutions of compounds 1 and 3 is not possible.

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Acknowledgements

This work was financially supported by the Russian Science Foundation (Project No. 16-13-10244-P).

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Authors and Affiliations

  1. N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia, 119991

    Anna V. Orlova, Nelly N. Malysheva & Leonid O. Kononov

  2. Department of Physics, M.V. Lomonosov Moscow State University, Build. 2, Leninskie Gory 1, Moscow, Russia, 119991

    Tatiana V. Laptinskaya

  3. Moscow Institute of Physics and Technology (National Research University), Institutsky per. 9, Dolgoprudnyi, Moscow Region, Russia, 141701

    Leonid O. Kononov

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  1. Anna V. Orlova
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  4. Leonid O. Kononov
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Orlova, A.V., Laptinskaya, T.V., Malysheva, N.N. et al. Light Scattering in Non-aqueous Solutions of Low-Molecular-Mass Compounds: Application for Supramer Analysis of Reaction Solutions. J Solution Chem 49, 629–644 (2020). https://doi.org/10.1007/s10953-020-00977-1

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