Hydrogen-bonded Systems Research Articles

Giant Thermopower of Hydrogen Ion Enhanced by a Strong Hydrogen Bond System.

Ionic thermoelectric materials based on organic polymers are of great significance for low-grade heat harvesting and self-powered wearable temperature sensing. Here, we demonstrate a poly(vinyl alcohol) (PVA) hydrogel that relies on the differential transport of H+ in PVA hydrogels with different degrees of crystallization. After the inorganic acid is infiltrated into the physically cross-linked PVA hydrogel, the ionic conductor exhibits a huge ionic thermopower of 38.20 mV K-1, which is more than twice the highest value reported for hydrogen ion transport thermoelectric materials. We attribute the enhanced thermally generated voltage to the movement of H+ in the strong hydrogen bond system of PVA hydrogels and the restrictive effect of the strong hydrogen bond system on anions. This ionic thermoelectric hydrogel opens up a new way for thermoelectric conversion devices using H+ as an energy carrier.

Low-dimensional compounds containing bioactive ligands. Part XVIII: Design, synthesis and crystal structural investigations of ionic heteroleptic Pd(II) complexes based on halo and nitro 8-hydroxyquinoline derivatives

The construction of coordination compounds with desired properties and fascinating structures is a topic of a great interest. In this context, noncovalent interactions can play a dominant role in synthesis, catalysis and design of materials. Here, new heteroleptic palladium(II) coordination compounds bearing 8-hydroxyquinolinium (8-HQH) as cation and [PdCl2(XQ)]- as anion, where HXQ = 5-chloro-7-iodo-8-hydroxyquinoline (1), 5-chloro-8-hydroxyquinoline (2), 5-nitro-8-hydroxyquinoline (3) or 5,7-dibromo-8-hydroxyquinoline (4), have been synthesized via one-pot reaction. Single crystal structure analysis reveals that Pd(II) is coordinated via the N- and O- donor atoms of the XQ ligands besides two cis-chlorido ligands. Both the anions and cations are connected by ionic interaction as well as hydrogen bonds to form infinite chains. The formed chains are assembled into 3D structures by π-π interactions between the aromatic quinoline rings. In addition, complexes 1 and 4 contain two water molecules of crystallization that are involved in the hydrogen bond system. Furthermore, elemental analysis and FT-IR spectroscopy were employed to prove the compositions of the produced compounds. The 1H and 13C NMR spectra measured in DMSO‑d6 confirm the presence of quinoline moieties in all the complexes and give a remarkable distinction between the coordinated and non-coordinated quinoline moieties. Collectively, this study provides a concrete starting point for the design and construction of ionic complexes of Pd(II) with 8-HQ derivatives including covalent and different non-covalent interactions and thus tuning the conformation, properties, and finally the functions of the compounds.

Hydrogen-bonding and nuclear quantum effects in clays.

Hydrogen bonds are of paramount importance in the chemistry of clays, mediating the interaction between the clay surface and water, and for some materials between separate layers. It is well-established that the accuracy of a computational model for clays depends on the level of theory at which the electronic structure is treated. However, for hydrogen-bonded systems, the motion of light H nuclei on the electronic potential energy surface is often affected by quantum delocalization. Using path integral molecular dynamics, we show that nuclear quantum effects lead to a relatively small change in the structure of clays, but one that is comparable to the variation incurred by treating the clay at different levels of electronic structure theory. Accounting for quantum effects weakens the hydrogen bonds in clays, with H-bonds between different layers of the clay affected more than those within the same layer; this is ascribed to the fact that the confinement of an H atom inside a layer is independent of its participation in hydrogen-bonding. More importantly, the weakening of hydrogen bonds by nuclear quantum effects causes changes in the vibrational spectra of these systems, significantly shifting the O-H stretching peaks and meaning that in order to fully understand these spectra by computational modeling, both electronic and nuclear quantum effects must be included. We show that after reparameterization of the popular clay forcefield CLAYFF, the O-H stretching region of their vibrational spectra better matches the experimental one, with no detriment to the model's agreement with other experimental properties.

Analysis of Weak Interactions in Crystals of Fenamic Acids–Ethacridine Complexes

While searching for new drugs based on combinations of fenamic acid and its derivatives with other pharmaceutically active substances, the syntheses of complexes of fenamic, flufenamic, mefenamic, and tolfenamic acids with ethacridine lactate were performed, and obtained complexes were characterized by X-ray diffraction. The inter- and intramolecular interactions were determined. An analysis of hydrogen bonds and other weak interactions was performed using Quantum Theory of Atoms in Molecules and noncovalent interaction approaches. The main force building the hydrogen-bond system are proton-accepting properties of the carboxylate group. Also, the presence of molecules of solvents in crystals results in the formation of interaction networks.

Towards bright dysprosium emitters: Single and combined effects of environmental symmetry, deuteration, and gadolinium dilution

With the aim of creating new light emitting systems, two new dysprosium complexes of formula [DyQcy3(H2O)] (1-Dy) and [H3O][DyQcy4] (2-Dy) (where HQcy = 1-phenyl-3-methyl-4-cyclohexylcarbonyl-pyrazol-5-one) have been synthesized and characterized by spectroscopy. The reaction conditions to address the synthesis toward these tris-(diketonate)dysprosium or tetrakis(diketonate)dysprosium complexes have been optimized. The Qcy ligand provides effective sensitization of the luminescence of Dy3+ ion. 1-Dy and 2-Dy have been investigated by single crystal X-ray diffraction analysis, both species being packed via a system of hydrogen bonds. The dependence of quantum yield and lifetime of the excited state of Dy3+ ions have been examined by implementing two common approaches: replacing protons with deuterium in the coordinated H2O or in cation H3O+ and diluting Dy3+ cations with Gd3+ ions, to suppress vibrational and concentration quenching, respectively. It has been found that deuteration turns out to be very effective on both quantum yield and lifetime, but only in the case of replacement of the inner-sphere water molecules. The strategy of gadolinium dilution leads in all cases to an increase in lifetime. In addition, the possibility of a subtle tuning of the luminescence color has been discovered due to the change in the gadolinium content and deuteration, and a white light luminescent (CIE 0.31, 0.34) composition has been obtained.

Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine.

Tuberculosis remains one of the most common diseases affecting developing countries due to difficult living conditions, the rapidly increasing resistance of M. tuberculosis strains and the small number of effective anti-tuberculosis drugs. This study concerns the relationship between molecular structure observed in a solid-state by X-ray diffraction and the 15N NMR of a group of pyridine derivatives, from which promising activity against M. tuberculosis was reported earlier. It was found that the compounds exist in two tautomeric forms: neutral and zwitterionic. The latter form forced the molecules to adopt a stable, unique, flat frame due to conjugation and the intramolecular hydrogen bond system. As the compounds exist in a zwitterionic form in the crystal state generally showing higher activity against tuberculosis, it may indicate that this geometry of molecules is the “active” form.

Hydrogen-bond super-amphiphile based drug delivery system: design, synthesis, and biological evaluation.

Drug delivery systems (DDSs) show great application prospects in tumor therapy. So far, physical encapsulation and covalent grafting were the two most common strategies for the construction of DDSs. However, physical encapsulation-based DDSs usually suffered from low drug loading capacity and poor stability, and covalent grafting-based DDSs might reduce the activity of original drug, which greatly limited their clinical application. Therefore, it is of great research value to design a new DDS with high drug loading capacity, robust stability, and original drug activity. Herein, we report a super-amphiphile based drug delivery system (HBS-DDS) through self-assembly induced by hydrogen bonds between amino-substituted N-heterocycles of the 1,3,5-triazines and hydrophilic carmofur (HCFU). The resulting HBS-DDS had a high drug loading capacity (38.1%) and robust stability. In addition, the drug delivery system exhibited pH-triggered size change and release of drugs because of the pH responsiveness of hydrogen bonds. In particular, the anticancer ability test showed that the HBS-DDS could be efficiently ingested by tumor cells, and its half-maximal inhibitory concentration (IC50 = 3.53 μg mL−1) for HeLa cells was close to that of free HCFU (IC50 = 5.54 μg mL−1). The hydrogen bond-based DDS represents a potential drug delivery system in tumor therapy.

Fick and Maxwell-Stefan Diffusion Coefficients in the Ternary Liquid Mixture of Acetone-Methanol-Chloroform

Fick diffusion coefficients are calculated by means of molecular simulation for liquid mixtures containing acetone, methanol and chloroform at 1 atm and 298 K for different compositions. For this means, Maxwell-Stefan (MS) diffusion coefficients were calculated using physical properties of the components and thermodynamic factors, Γ, using three different models of Wilson, NRTL and UNIQUAC. Because of the lack of experimental data for Fick diffusivities for ternary system, the validity of the model was tested by comparing Fick diffusivities obtained for binary subsystems with experimental data for acetone- chloroform system. The results were in good agreement. So the Fick coefficients, Maxwell-Stefan diffusion coefficient and the thermodynamic factors were predicted for the ternary mixture as well as its binary subsystems by molecular simulation in a consistent manner. The presented ternary diffusion data should facilitate the development of aggregated predictive models for diffusion coefficients of polar and hydrogen-bonding systems and allows for an efficient and consistent prediction of multicomponent Fick diffusion coefficients from molecular models.

MIXED-LIGAND HETEROMETALLIC COMPLEXES OF Ge(IV)-M2+ (Mn, Fe, Co, Ni, Zn) WITH 1,3-DIAMINO-2-HYDROXYPROPANE N,N,N',N'-TETRAACETIC ACID

There have been developed a novel synthetic method that allowed to obtain raw of mixed-ligand heterometallic binuclear complexes of Ge(IV)-M2+ (Mn, Fe, Co, Ni, Zn) with 1,3-diamino‑2-hydroxypropane N, N, N’, N’-tetraacetic acid (H5hpdta). Compounds have been characterized by the set of methods: elemental analysis, thermogravimetry, IR‑spectroscopy, spectrum of diffuse reflection, magnetic suspensibility. According to the elemental analysis, the molar ratio Ge: M: H5hpdta: bipy= 1:1:1:1 in the obtained compounds 1‑5 corresponds to the formula [(H2O)(OH)Ge(m-hpdta)M(bipy)]·nН2О (M=Mn n=3 (1), Fe n=2 (2), Co n=4 (3), Ni n=4 (4), Zn n=3 (5). Complexes have yellow (1), red (2), orange (3), violet (4) and pink (5) colors and are stable on air. Compounds 1‑5 exist in the form of crystal hydrates, that contain certain amount of water molecules, that are eliminated into the gas phase while heating in the wide range of temperatures (t=80‑250 °C), which is accompanied with the low-temperature endothermic effect. This indicates the presence of a system of stable hydrogen bonds in their crystal structure. Analysis of the IR‑spectra 1‑5 revealed that form and coordination of ligands is similar. Deprotonation of all carboxylic groups in the ligands (H5hpdta) and their bonding to germanium and d-metal is confirmed with the absence in the IR‑spectra 1‑5 absorption bands characteristic for the free СООН H5hpdta (1716 сm‑1) and nas(СОО-) і ns(СОО-) bands. Disappearance of the ν(С-OН)-1210 сm‑1 and appearance of the ν(С-O)alk., νas(Ge-O-M), νs(Ge-O- M) absorption band indicates that OH‑group of H5hpdta is deprotonated and performs bridging function. 2,2`-bipyridine bidentatly coordinates to the d-metal, binds to the O, N‑atoms of hpdta5- ligand and reaches coordination number 6. The last ligand plays the bringing role between Ge-dmetal, shows itself as ditopic, octadentate in total. According to the magnetic moments of 3, 4 and their diffuse reflection spectra, polyhedrons of Co (II), Ni (II) are octahedrons, which are realized due to the bidentate coordination of bipyridine and four bonds with nitrogen and oxygen of hpdta5-. Structure of heterometallic binuclear complexes 1‑5 is similar. Ligand hpdta5- shows itself as octadentate ditopic, all carboxylate groups monodentatly coordinate to metals, oxygen atom of the deprotonated OH‑group performs the bridging function.

Synthesis of self‐healing supramolecular waterborne polyurethane with quadruple hydrogen bonds via ureidotriazine

AbstractA supramolecular waterborne polyurethane (SWPU) with excellent mechanical and self‐healing properties simultaneously is reported in this work. Herein, the SWPU were synthesized by using 2,4‐diamino‐6‐undecyl‐1,3,5‐triazine react with isophorone diisocyanate to introduce ureidotriazine (UTr) structures into the main chain of polyurethane that can self‐assemble to form quadruple hydrogen bonds systems. A higher dimerization constant obtained through introducing two intramolecular hexatomic ring hydrogen bonds into the UTr structure, and the hydrophobicity, plasticity brought by the undecyl group on the triazine ring are beneficial to make a great balance between the binding strength for mechanical performance and the chain reversibility, mobility for self‐healing. Owing to the accuracy design, the SWPU exhibits high tensile stress (33.85 MPa) and excellent self‐healing ability (90.52%), which shows an enormous application potential in the field of functional coatings and adhesives.

Mapping Quantum Chemical Dynamics Problems to Spin-Lattice Simulators.

The accurate computational determination of chemical, materials, biological, and atmospheric properties has a critical impact on a wide range of health and environmental problems, but is deeply limited by the computational scaling of quantum mechanical methods. The complexity of quantum chemical studies arises from the steep algebraic scaling of electron correlation methods and the exponential scaling in studying nuclear dynamics and molecular flexibility. To date, efforts to apply quantum hardware to such quantum chemistry problems have focused primarily on electron correlation. Here, we provide a framework that allows for the solution of quantum chemical nuclear dynamics by mapping these to quantum spin-lattice simulators. Using the example case of a short-strong hydrogen-bonded system, we construct the Hamiltonian for the nuclear degrees of freedom on a single Born-Oppenheimer surface and show how it can be transformed to a generalized Ising model Hamiltonian. We then demonstrate a method to determine the local fields and spin-spin couplings needed to identically match the molecular and spin-lattice Hamiltonians. We describe a protocol to determine the on-site and intersite coupling parameters of this Ising Hamiltonian from the Born-Oppenheimer potential and nuclear kinetic energy operator. Our approach represents a paradigm shift in the methods used to study quantum nuclear dynamics, opening the possibility to solve both electronic structure and nuclear dynamics problems using quantum computing systems.

Multisubstituted Imidazolo[4,5-d]pyridazine Fused Ring System Resulting from Nitroamine-Nitroimine Tautomerism.

A series of multisubstituted imidazolo[4,5-d]pyridazine fused ring compounds was synthesized in which nitroamine-nitroimine tautomerism is exhibited. The electrostatic potential indicates that the nitroimino group has the lowest negative value, second only to the nitro group, culminating in the nitroamino area, which has the highest positive value. In addition, a strong hydrogen bond system which arises from the newly formed nitroimino tautomer suggests that the nitroimino is more stable than its nitroamino analogue.

Dipole–dipole interactions effects on mobility and conductivity of ionic and bonded defects in hydrogen-bonded chains

Defect formation and transport in a hydrogen-bonded system is studied via a two-sublattice soliton-bearing one-dimensional model. Our two component model completes and extends our previous study (Tchakoutio Nguetcho and Kofane, 2007; Tchakoutio Nguetcho et al., 2008; Li et al., 2015) made on the dynamics of defects in a quasi-one-dimensional nonlinear model of complex hydrogen bond systems. The inclusion of dipole–dipole interactions provides a new class of differential equations possessing several key parameters and many singular straight lines. In order to evaluate and measure the variations effects on each interaction parameter, we use dynamic system methods to first say what are really the key parameters of the system, and then discuss on phase portraits bifurcations to derive a variety of exotic solutions corresponding to phase trajectories under different parameter conditions. Among the rich variety of soliton patterns obtained, we focus our attention to kink (antikink) solutions. The response of these solitonic defects to an externally applied DC electric field makes this system an excellent model to describe the protonic conductivity in complex hydrogen-bonded networks. Therefore, we evaluate analytically the effect of dipole–dipole interactions on the mobility of the kink–antikink pair and the specific electrical-conductivity of the protons transfer.

Hydrogen Bond Strength-Mediated Self-Assembly of Supramolecular Nanogels for Selective and Effective Cancer Treatment.

This study provides a significant contribution to the development of multiple hydrogen-bonded supramolecular nanocarrier systems by demonstrating that controlling the hydrogen bond strength within supramolecular polymers represents a crucial factor to tailor the drug delivery performance and enhance the effectiveness of cancer therapy. Herein, we successfully developed two kinds of poly(ethylene glycol)-based telechelic polymers Cy-PEG and UrCy-PEG having self-constituted double and quadruple hydrogen-bonding cytosine (Cy) and ureido-cytosine (UrCy) end-capped groups, respectively, which directly assemble into spherical nanogels with a number of interesting physical characteristics in aqueous solutions. The UrCy-PEG nanogels containing quadruple hydrogen-bonded UrCy dimers exhibited excellent long-term structural stability in a serum-containing biological medium, whereas the double hydrogen-bonded Cy moieties could not maintain the structural integrity of the Cy-PEG nanogels. More importantly, after the drug encapsulation process, a series of in vitro experiments clearly confirmed that drug-loaded UrCy-PEG nanogels induced selective apoptotic cell death in cancer cells without causing significant cytotoxicity to healthy cells, while drug-loaded Cy-PEG nanogels exerted nonselective cytotoxicity toward both cancer and normal cells, indicating that increasing the strength of hydrogen bonds in nanogels plays a key role in enhancing the selective cellular uptake and cytotoxicity of drugs and the subsequent induction of apoptosis in cancer cells.

Elucidation of Charge Contribution in Iridium-Chelated Hydrogen-Bonding Systems

We present two iridium complexes 1H + and 2H + that contain cationic ligands to extend the knowledge of charge-assisted hydrogen bonding (CAHB), which counts among the strongest non-covalent bonding interactions. Upon protonation, both complexes were converted into new hydrogen-bonding arrays with various selectivity for respective H-bonding partners. This study compares the association strengths of four hydrogen-bonding co-systems, emphasizing the roles of CAHB in supramolecular systems. We determined that the cationic charge in these systems contributed up to 2.7 kJ mol−1 in the H-bonding complexation processes.

Experimental and ab initio molecular dynamics study of hydrogen-bond systems in selected crystals

Experimental and <i>ab initio</i> molecular dynamics study of hydrogen-bond systems in selected crystals

Insight into the role of exopolysaccharide in determining the structural stability of aerobic granular sludge

Extracellular polymeric substances (EPS) have a critical contribution to the stability of aerobic granular sludge (AGS), but the mechanism and details of EPS composition and function are far from clear. This work investigated the contribution of exopolysaccharide (PS) to maintaining the structural stability of AGS. The results revealed that PS hydrolysis induced by α-amylase, dextranase and cellulase significantly decreased the granular stability, whereas a substantial content reduction of extracellular protein (PN) was also observed. It was also found that hydrolysis of PS led to a decrease of sludge hydrophobicity, granular gel mechanical strength by 14.09 %, 38.67 %, respectively, and an increase of surface free energy by 49.59 %, which is not conducive to granular stability. Through fluorescent staining, existence of large amounts of PS and PN conjugates in EPS matrix was verified. It was proposed that these conjugates with PS as skeleton (PS-PN) dominate granular stability by affecting hydrophobicity interactions and hydrogen bonds system, which are two important parameters to gel properties, constituting a crucial finding of this work. This study offers an supplementation of EPS system theory and granular stability mechanism.

HYDROGEN BONDS IN THE FORMATION OF COPPER(II) 1,10-PHENANTHROLINE HYDROXYCARBOXYLATOGERMANATE CRYSTALS USING HIRSHFELD SURFACE ANALYSIS

This article is dedicated to the investigation of crystalline structure in the complex cation-anionic compounds Cu(Phen)2Cl]2[Ge(HCit)2]⋅6H2O (I), [Cu(Phen)3]2[Ge2(OH)(HTart)(μ-Tart)2]·11H2O (II), [CuCl(Phen)2]4[{Ge2(OH)2(μ-Tart)2}Cl2]·4Н2О (III), [Cu(Phen)3]2[(OH)2Ge2(μ-HXylar)4Ge2(μ-OH)2]·8H2O (IV), [CuCl(Phen)2]4[(OH)2Ge2(μ-HXylar)4Ge2(μ-OH)2]·8H2O (V) using Hirshfeld surface analysis. This method has showed itself as an effective tool for analysis of intermolecular interactions, such as hydrogen bonds or weaker C…H and С…Н…p connections. Three-dimensional picture of close interactions in the crystal was built for each of the compounds I–V, where short connections are red-colored, while others – weaker and shorter – are light areas and small spots. It was established that in the structures of all compounds different types of hydrogen bonds are presented: bifurcate connections, symmetrical О-Н…О, С-Н…С and asymmetrical ones with water molecules. Two-dimensional histograms – 2D-fingerprint plots, allowed to evaluate quantitively connections in the crystals and establish that H…O/O…H and H…H interactions make the biggest contribution to the total surface area. The presence of the big number of crystallization water molecules is determinant for the formation of complex system of hydrogen bonds and strengthening of the structure, that otherwise would be unstable because of the big size of cations and anions. Due to the fact, that all compounds have the same complexing agent Ge(IV), structure of the anion is determined by polydentate ligand. Obtained results are important for the further development of the water role in the processes of crystallization, crystal formation, electrical dissociation and, especially, dissolving of coordination compounds in biological systems.

Engineering of the XY Magnetic Layered System with Adeninium Cations: Monocrystalline Angle-Resolved Studies of Nonlinear Magnetic Susceptibility.

An original example of modular crystal engineering involving molecular magnetic {CuII[WV(CN)8]}− bilayers and adeninium cations (AdeH+) toward the new layered molecular magnet (AdeH){CuII[WV(CN)8]}·2H2O (1) is presented. 1 crystallizes within the monoclinic C2 space group (a = 41.3174(12), b = 7.0727(3), c = 7.3180(2) Å, β = 93.119(3)°, and V = 2135 Å3). The bilayer topology is based on a stereochemical matching between the square pyramidal shape of CuII moiety and the bicapped trigonal prismatic shape of [WV(μ-CN)5(CN)3], and the separation between bilayers is significantly increased (by ∼50%; from ca. 9.5 to ca. 14.5 Å) compared to several former analogues in this family. This was achieved via a unique combination of (i) a 1D ribbonlike hydrogen bond system {AdeH+···H2O···AdeH+···}∞ exploiting planar water-assisted Hoogsteen···Sugar synthons with (ii) parallel 1D π–π stacks {AdeH+···AdeH+}∞. In-plane 2D XY magnetism is characterized by a Tc close to 33 K, Hc,in-plane = 60 Oe, and Hc,out-of-plane = 750 Oe, high values of in-plane γ critical exponents (γb = 2.34(6) for H||b and γc = 2.16(5) for H||c), and a Berezinskii–Kosterlitz–Thouless (BKT) topological phase transition, deduced from crystal-orientation-dependent scaling analysis. The obtained values of in-plane ν critical exponents, νb = 0.48(5) for H||b and νc = 0.49(3) for H||c, confirm the BKT transition (νBKT = 0.5). Full-range angle-resolved monocrystalline magnetic measurements supported by dedicated calculations indicated the occurrence of nonlinear susceptibility performance within the easy plane in a magnetically ordered state. We refer the occurrence of this phenomenon to spontaneous resolution in the C2 space group, a tandem not observed in studies on previous analogues and rarely reported in the field of molecular materials. The above magneto-supramolecular strategy may provide a novel means for the design of 2D molecular magnetic networks and help to uncover the inherent phenomena.

Hydrogen Bonds, Topologies, Energy Frameworks and Solubilities of Five Sorafenib Salts.

Sorafenib (Sor) is an oral multi-kinase inhibitor, but its water solubility is very low. To improve its solubility, sorafenib hydrochloride hydrate, sorafenib hydrobromide and sorafenib hydrobromide hydrate were prepared in the mixed solvent of the corresponding acid solution, and tetrahydrofuran (THF). The crystal structures of sorafenib hydrochloride trihydrate (Sor·HCl.3H2O), 4-(4-{3-[4-chloro-3-(trifluoro-methyl)phenyl]ureido}phenoxy)-2-(N-methylcarbamoyl) pyridinium hydrochloride trihydrate, C21H17ClF3N4O3+·Cl−.3H2O (I), sorafenib hydrochloride monohydrate (Sor·HCl.H2O), C21H17ClF3N4O3+·Cl−.H2O (II), its solvated form (sorafenib hydrochloride monohydrate monotetrahydrofuran (Sor·HCl.H2O.THF), C21H17ClF3N4O3+·Cl−.H2O.C4H8O (III)), sorafenib hydrobromide (Sor·HBr), 4-(4-{3-[4-chloro-3-(trifluoro-methyl)phenyl]ureido}phenoxy)-2-(N-methylcarbamoyl) pyridinium hydrobromide, C21H17ClF3N4O3+·Br− (IV) and sorafenib hydrobromide monohydrate (Sor·HBr.H2O), C21H17ClF3N4O3+·Br−.H2O (V) were analysed. Their hydrogen bond systems and topologies were investigated. The results showed the distinct roles of water molecules in stabilizing their crystal structures. Moreover, (II) and (V) were isomorphous crystal structures with the same space group P21/n, and similar unit cell dimensions. The predicted morphologies of these forms based on the BFDH model matched well with experimental morphologies. The energy frameworks showed that (I), and (IV) might have better tabletability than (II) and (V). Moreover, the solubility and dissolution rate data exhibited an improvement in the solubility of these salts compared with the free drug.