Abstract
The peculiarities of interatomic interactions formed by fluorine atoms were studied in four tosylate derivatives p-CH3C6H4OSO2CH2CF2CF3 and p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5, 7) using X-ray diffraction and quantum chemical calculations. Compounds p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) were crystallized in several polymorph modifications. Analysis of intermolecular bonding was carried out using QTAIM approach and energy partitioning. All compounds are characterized by crystal packing of similar type and the contribution of intermolecular interactions formed by fluorine atoms to lattice energy is raised along with the increase of their amount. The energy of intra- and intermolecular F…F interactions is varied in range 0.5–13.0 kJ/mol. Total contribution of F…F interactions to lattice energy does not exceed 40%. Crystal structures of studied compounds are stabilized mainly by C-H…O and C-H…F weak hydrogen bonds. The analysis of intermolecular interactions and lattice energies in polymorphs of p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) has shown that most stabilized are characterized by the least contribution of F…F interactions.
Highlights
Organosulfur compounds containing fluorinated hydrocarbon moieties are usually considered as dangerous hydrocarbon pollutants that destroy cell membranes [1,2]
Perfluoroalkyl sulfonates, perfluoroalkyl sulfoacids, and sulfamides are the most dangerous and pervasive in environment owing to their high stability and surfactant properties
Perfluorooctane sulfuric acid can occupy the position between peptide chains of serum albumin [6] mostly via weak van-der-Waals H . . . F interactions
Summary
Organosulfur compounds containing fluorinated hydrocarbon moieties are usually considered as dangerous hydrocarbon pollutants that destroy cell membranes [1,2]. Among these compounds, perfluoroalkyl sulfonates, perfluoroalkyl sulfoacids, and sulfamides are the most dangerous and pervasive in environment owing to their high stability and surfactant properties. The presence of perfluorinated hydrocarbon moiety plays special role in binding of these compounds with biomolecules in solution and in complexes with proteins via hydrophobic interactions. Perfluorooctane sulfuric acid can occupy the position between peptide chains of serum albumin [6] mostly via weak van-der-Waals H . Perfluoroalkyl chains can form aggregates (molecular ensembles, micelles [7], liquid crystal phases [8])
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