2D and 3D‐QSPR Models for the Fluorophilicity of Organic Compounds in Consideration of Chirality

Abstract

Fluorous biphase system (FBS) exhibits significant prospect in synthesis and catalysis fields. With the development of FBS, the design and prediction on the fluorophilicity of compounds show major importance. QSPR models are established by using threedimensional structural descriptors derived from VolSurf program and two-dimensional topological descriptors derived from Tsar program. Good results are received and the training set model has satisfactory predictive capability for the test set. MLR method is applicative for Tsar descriptors and the equation shows that more number of F atoms in the compound will result in higher fluorophilicity. PLS analysis is suitable for VolSurf descriptors. Analysis on VolSurf descriptors demonstrates that large hydrophilic regions at medium energy level are beneficial to the fluorophilicity. The capacity factor is negative correlation with the fluorophilicity, so do the best local interaction energy minimum and its distance. High hydrophobic descriptor values and large hydrogen bond acceptor regions at medium energy levels are favorable elements. High anionic regions, low POL value and high MW are advantageous to the fluorophilicity. 3D-VolSurf descriptors (R 2 ¼ 0.976, Q 2 ¼ 0.966) are more satisfying and suitable to build the QSPR model for the fluorophilicity than other descriptors. In addition, chirality has different extent influence on the calculated result for the different chiral molecules or with the different modeling methods. Using single configuration to compute for chiral molecules will be hopeful to bring about more accurate and credible result.

Quantitative Structure–Sorption Relationships of Pesticides Used in the Sugarcane Industry in the Northern Coastal Area of Paraíba State, Brazil

“…In descending order of LgD6, compounds 6, 9, 13, 2, 1, 8, and 10 show that the larger the octanol-water partition coefficient in an acid medium, the more sorbed the molecule is onto the soil. Hydrophobic Surface Area (HSA) and Polarisability (POL) are in the first quadrant, relatively near to log K oc ; the latter is an estimation of the average molecular polarisability based on the structure of the compounds (and not any molecular field; [17][18][19][20][21][22][23][24][25][26][27][28][29].…”

“…GRID fields were generated, by using VolSurf + v1.0.7 software, for all the probes (H 2 O, water; DRY, hydrophobic; N1, amide nitrogen; O, carbonyl oxygen), and can be visualised by selecting a specific energy level. The VolSurf program generated 56 non-MIF descriptors, by using several algorithms, and was used in some of the QSPR studies to predict the solubility of organic compounds in different ionic liquids (21), the fluorophilicity of organic compounds (22), and the retention of triphenylmethane derivatives (23).…”

“…When the integy moments are high, this indicates a concentration of hydrated regions in only one part of the molecular surface. CW5 and CW6 descriptors, located in the 4th quadrant, are capacity factors and encode hydrophilic volume over the total molecular surface, at energy levels of -3.0 and -4.0kcal/mol, respectively (17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29).…”