QSPR models for water solubility of ammonium hexafluorosilicates: analysis of the effects of hydrogen bonds
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ORIGINAL RESEARCH
QSPR models for water solubility of ammonium hexafluorosilicates: analysis of the effects of hydrogen bonds Vladimir Gelmboldt 1 & Luidmyla Ognichenko 2
&
Ivan Shyshkin 1 & Victor Kuz’min 2
Received: 20 August 2020 / Accepted: 22 September 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract In the present study, adequate quantitative structure-activity relationship (QSAR) models were developed to analyze the water solubility of some ammonium hexafluorosilicates. All models were developed using structural descriptors calculated by the SiRMS method based on the simplex representation of the molecular structure and Dragon descriptors. Log P, equalized electronegativity, molecular refraction, and molecular weight were used as integral descriptors in addition to 2D structural descriptors. All QSAR models were obtained using the partial least squares (PLS) method. Model M1 examined the influence of various physicochemical and structural factors on the water solubility of the studied compounds. The interpretation results are consistent with the qualitative data of previous experimental works. It was possible to detail the features of the hydrogen bonds effect on the water solubility for investigated compounds The non-trivial nature of the effect of the hydrogen bond was also shown. QSPR model M2 could predict the solubility of new compounds of the studied type with satisfactory accuracy. Keywords QSAR models . Ammonium hexafluorosilicates . Water solubility . SiRMS approach . Hydrogen bond
Introduction Water solubility is one of the most important macroscopic characteristics of a substance. It plays a key role in solving various problems of chemical technology, assessing the dynamics distribution of pollutants in ecosystems and dosing of drugs and their transport. In particular, water solubility assessment is a mandatory procedure for all drug candidates [1]. To date, there are many different QSPR models for describing the water solubility (WSol) of various substances [2–4]. Most of them deal with organic compounds such as known or potential drugs, pesticides, and other toxicants [5–7]. The primary goal
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01652-3) contains supplementary material, which is available to authorized users. * Luidmyla Ognichenko [email protected] 1
Department of Pharmaceutical Chemistry, Odessa National Medical University, Odessa 65082, Ukraine
2
Department of Molecular Structures and Chemoinformatics, A. V. Bogatsky Physical-Chemical Institute NAS of Ukraine, Odessa 65080, Ukraine
of these models is water solubility prediction and virtual screening. Unfortunately, only a few works carry out a systematic interpretation of QSPR models to determine the basic structural and physicochemical factors which control WSol [8, 9]. These works highlight the important role of hydrogen bonds (HB) in the process of substances dissolution in water. Their general conclusion is that the presence of hydrop
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