Polar Hydroxy Groups Research Articles

Low-κ, low CTE, high-temperature epoxy resin with high storage modulus based on spirobisindane for high-frequency electronic circuit field

High-temperature thermosetting resin with low dielectric constant (κ), low thermal expansion coefficient (CTE), and high modulus are drawing more and more attention from scientists and engineers in the field of the high-frequency circuit, 5G and 6G communication networks to improve the signal transmission speed. Epoxy resin, as one of the important thermosetting resin members, possesses excellent properties such as heat resistance, cohesiveness, and reactivity. However, Epoxy resin was usually mixed with different inorganic fillers to meet the above requirements, especially to decrease the κ and CTE. In this work, a new class of spirobisindane epoxy resin monomer (TSDEP) was synthesized by a classic two-step method based on 3,3,3′,3′-tetramethyl-1,1′-spirobisindane-6,6′-diol (TSD). Due to the highly distorted rigid structure of TSD, the movement of the TSDEP molecular segment is subject to more restrictions after being cured, and the free volume will increase. After cured by 4,4′-diamino diphenyl sulfone (DDS), the TSDEP/DDS resin exhibited many desirable physical properties, e.g., low dielectric constant (∼3.45, 1 MHz), low dielectric loss (∼0.025, 1 MHz), low coefficient of thermal expansion (CTE, 72 ppm/ °C, 35–150 °C), high glass transition temperature (Tg > 241 °C) and high thermal stability (Td5%∼400 °C). Furthermore, TSDEP/DDS exhibited excellent mechanical rigidity with a storage modulus of ∼ 3.1 GPa. Compared with TSDEP/DDS, 4-methylhexahydrophthalic anhydride (MHHPA) cured TSDEP system showed lower κ (∼3.09) and dielectric loss (0.015) due to weaker polar ester groups instead of more polar hydroxy groups.

Analysis of Softwood Lignans by Comprehensive Two-Dimensional Liquid Chromatography.

Lignans constitute a large group of phenolic plant secondary metabolites possessing high bioactivity. Their accurate determination in plant extracts with a complex chemical composition is challenging and requires advanced separation techniques. In the present study, a new approach to the determination of lignans in coniferous knotwood extracts as the promising industrial-scale source of such compounds based on comprehensive two-dimensional liquid chromatography separation and UV spectrophotometric detection is proposed. First and second-dimension column screening showed that the best results can be obtained using a combination of non-polar and polar hydroxy group embedded octadecyl stationary phases with moderate (~40%) "orthogonality". The optimization of LC × LC separation conditions allowed for the development of a new method for the quantification of the five lignans (secoisolariciresinol, matairesinol, pinoresinol, 7-hydroxymatairesinol, and nortrachelogenin) in knotwood extracts with limits of quantification in the range of 0.27-0.95 mg L-1 and a linear concentration range covering at least two orders of magnitude. Testing the developed method on coniferous (larch, fir, spruce, and pine) knotwood extracts demonstrated the high selectivity of the analysis and the advantages of LC × LC in the separation and accurate quantification of the compounds co-eluting in one-dimensional HPLC.

Pore Space Partitioning MIL-88(Co): Developing Robust Adsorbents for CO2/CH4 Separation Featured with High CO2 Adsorption and Rapid Desorption.

Metal-organic frameworks (MOFs) have attracted significant attention as sorbents for gas separation and purification. Ideally, an industrially potential adsorbent should combine exceptional gas uptake, excellent stability, and a lower regeneration energy; however, it remains a great challenge. Here, by utilizing the pore space partition (PSP) strategy, we develop three isostructural MOF materials (Co-BDC-TPB, Co-DCBDC-TPB, and Co-DOBDC-TPB) based on pristine MIL-88(Co). The three pore-space-partitioned crystalline microporous MOFs have triangular bipyramid cages and segmented one-dimensional channels, and among them, Co-DOBDC-TPB exhibits the highest CO2 uptake capacity (4.35 mmol g-1) and good CO2/N2 (29.7) and CO2/CH4 (6.2) selectivity. The selectivity-capacity synergy endows it with excellent CO2/N2 and CO2/CH4 separation performance. Moreover, Co-DOBDC-TPB can complete desorption within 10 min. The satisfactory CO2 adsorption ability can be attributed to both microporous aperture arising from PSP and modification of the pore surface by the polar hydroxy group, which enhances the interaction between Co-DOBDC-TPB and CO2 molecules significantly. The exceptional regeneration property may be due to its lower CO2 isosteric heat of adsorption (23.6 kJ/mol). The developed pore-space-partitioned MIL-88(Co) material Co-DOBDC-TPB may have potential application to flue gas and natural gas purification.

In situ fabrication of silver/polyimide composite films with enhanced heat dissipation.

In this study, silver/polyimide (Ag/PI) composite films with enhanced heat dissipation properties were prepared. Ag was formed in situ by reducing AgNO3 at various locations according to the reduction method. Two different types of soluble PIs capable of solution processing were used, namely Matrimid and hydroxy polyimide (HPI). Unlike Matrimid with bulky substituents, HPI with polar hydroxy groups formed ion–dipole interactions with Ag ions to form Ag particles with uniform size distribution. The location and distribution of Ag particles affect the heat emission characteristics of the composite films, resulting in better heat dissipation properties with the thermally and photochemically reduced Ag/HPI films having more Ag particles distributed inside of the films than the chemically reduced films.

Reorganization of an Amphiphilic Glassy Polymer Surface in Contact with Water Probed by Contact Angle and Sum Frequency Generation Spectroscopy

We address the question of how a surface of a glassy polymer reorganizes after coming in contact with water. Because contact angle hysteresis measurements are also affected by surface roughness and chemical heterogeneity, we have used surface-sensitive sum frequency generation spectroscopy (SFG) in conjunction with water contact angles to answer this question. To increase the magnitude of the surface reorganization, we have designed an amphiphilic polymer, poly(α-hydroxymethyl-n-butyl acrylate) (PHNB), to study the changes in the structure of polar hydroxy groups and nonpolar (methyl and methylene) groups at the interface. The SFG and the water contact angles show that reorganization does occur for PHNB below Tg. However, complete reorganization requires heating the sample above the bulk Tg. These heating experiments were conducted by first heating the sample in the presence of water and then followed by cooling the sample to room temperature in the presence of water to lock the changes in the surface str...

What contributes to an effective mannose recognition domain?

In general, carbohydrate–lectin interactions are characterized by high specificity but also low affinity. The main reason for the low affinities are desolvation costs, due to the numerous hydroxy groups present on the ligand, together with the typically polar surface of the binding sites. Nonetheless, nature has evolved strategies to overcome this hurdle, most prominently in relation to carbohydrate–lectin interactions of the innate immune system but also in bacterial adhesion, a process key for the bacterium’s survival. In an effort to better understand the particular characteristics, which contribute to a successful carbohydrate recognition domain, the mannose-binding sites of six C-type lectins and of three bacterial adhesins were analyzed. One important finding is that the high enthalpic penalties caused by desolvation can only be compensated for by the number and quality of hydrogen bonds formed by each of the polar hydroxy groups engaged in the binding process. In addition, since mammalian mannose-binding sites are in general flat and solvent exposed, the half-lives of carbohydrate–lectin complexes are rather short since water molecules can easily access and displace the ligand from the binding site. In contrast, the bacterial lectin FimH benefits from a deep mannose-binding site, leading to a substantial improvement in the off-rate. Together with both a catch-bond mechanism (i.e., improvement of affinity under shear stress) and multivalency, two methods commonly utilized by pathogens, the affinity of the carbohydrate–FimH interaction can be further improved. Including those just described, the various approaches explored by nature to optimize selectivity and affinity of carbohydrate–lectin interactions offer interesting therapeutic perspectives for the development of carbohydrate-based drugs.

Synthesis and properties of cyclotriphosphazene and perfluoropolyether‐based lubricant with polar functional groups

AbstractA novel hard disk lubricant IDL2 was synthesised by reacting sodium 4‐((2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)methoxy)phenoate with hexachlorocyclotriphosphazene, followed by treatment with 1H,1H‐perfluoro‐3,6,9‐trioxatridecan‐1‐ol in the presence of sodium hydride and subsequent hydrolysis using sulfuric acid. The chemical structure of IDL2 was confirmed by proton nuclear magnetic resonance (1H NMR), phosphorus‐31 (31P) NMR spectroscopy and mass spectrometer. The thermal property of IDL2 was analysed using thermal gravimetric analysis (TGA) and it shows better thermal stability than two commercial lubricants Z‐DOL and Z‐Tetraol with two and four terminal hydroxy groups, respectively. IDL2 was found to have comparable hydrophobicity to commercial lubricants Z‐DOL, A20H and Z‐Tetraol with water contact angles in the range of 78 – 85°, revealing that IDL2 has analogous surface energy to these commercial lubricants. IDL2 exhibits comparable friction coefficient to A20H and Z‐Tetraol, but much lower than Z‐DOL. More interestingly, it has a much high bonding ratio when compared with commonly used commercial lubricants under the same testing conditions due to the presence of two polar hydroxy groups, which enhance the interaction between lubricant and substrate. These promising properties of IDL2 show that it would be very potential for real application as a hard disk drive lubricant. Copyright © 2016 John Wiley & Sons, Ltd.

Interaction of G protein coupled receptors and cholesterol

G protein coupled receptors (GPCRs) form the largest receptor superfamily in eukaryotic cells. Owing to their seven transmembrane helices, large parts of these proteins are embedded in the cholesterol-rich plasma membrane bilayer. Thus, GPCRs are always in proximity to cholesterol. Some of them are functionally dependent on the specific presence of cholesterol. Over the last years, enormous progress on receptor structures has been achieved. While lipophilic ligands other than cholesterol have been shown to bind either inside the helix bundle or at the receptor-lipid interface, the binding site of cholesterol was either a single transmembrane helix or a groove between two or more transmembrane helices. A clear preference for one of the two membrane leaflets has not been observed. Not surprisingly, many hydrophobic residues (primarily leucine and isoleucine) were found to be involved in cholesterol binding. In most cases, the rough β-face of cholesterol contacted the transmembrane helix bundle rather than the surrounding lipid matrix. The polar hydroxy group of cholesterol was localized near the water-membrane interface with potential hydrogen bonding to residues in receptor loop regions. Although a canonical motif, designated as CCM site, was detected as a specific cholesterol binding site in case of the β2AR, this site was not found to be occupied by cholesterol in other GPCRs possessing the same motif. Cholesterol-receptor interactions can increase the compactness of the receptor structure and are able to enhance the conformational stability towards active or inactive receptor states. Overall, all current data suggest a high plasticity of cholesterol interaction sites in GPCRs.

Trans–cis isomerization of arylether dendrimers with azobenzene core and terminal hydroxy groups

Azobenzene-cored arylether dendrimers 2a–2c with polar hydroxy groups at the periphery have been prepared from hydroboration–oxidation reaction of azobenzene-cored arylether dendrimers 1a–1c with nonpolar vinyl groups at the periphery. Trans → cis photoisomerization of central azo group has been investigated by UV–vis spectral changes after photolysis. The results show that dendrimers 1a–1c and 2a–2c in methanol/dichloromethane (1/1, v/v) have carried out trans–cis isomerization. Reaction rate for trans → cis photoisomerization of 2a–2c with polar hydroxy groups increases with increasing generation upon irradiation of 350 nm. On the other hand, the reaction rate of cis → trans thermal back isomerization for 2a–2c decreases with increasing the generation. This result is somewhat different from that for 1a–1c with nonpolar vinyl groups. Both the reaction rates of trans → cis photoisomerization and cis → trans thermal back isomerization for 1a–1c decrease in higher generation.

Synthesis, physical and mesomorphic properties of Schiff's base esters containing ortho‐, meta‐ and para‐substituents in benzylidene‐4′‐alkanoyloxyanilines

Three series of Schiff's base esters, 2‐hydroxy‐4‐methoxybenzylidene‐4′‐alkanoyloxyaniline, 2‐hydroxy‐3‐methoxybenzylidene‐4′‐alkanoyloxyaniline and 3‐methoxy‐4‐alkanoyloxybenzylidene‐4′‐alkanoyloxyaniline, which possess mono‐ and di‐substituted moieties at both ends of the molecules have been synthesized and their mesomorphic properties investigated along with physical characterization (elemental analysis, mass spectrometry, Fourier transform IR and high resolution NMR). The effect of lateral methoxy and polar hydroxy groups on the mesomorphism of the title compounds was studied, based on the thermal properties and textural analysis. The results indicate that compounds with the larger number of carbons in the alkyl chain prefer smectic phase formation and possess higher transition temperatures and molecular polarizability along the long axis. Further analysis shows that the greater shielding effect (through the formation of intramolecular interaction) leads to lower molecular broadening and results in higher clearing points. Increase in melting point due to the lengthening of the alkyl chain is associated with the increase in van der Waals attraction between the molecules. These compounds exhibit nematic, smectic (SmA and SmC) phases depending on the type and position of the substituents.

Molecular dynamics simulations of the adsorption of industrial relevant silane molecules at a zinc oxide surface

The physical behavior of different adsorbed silane molecules (octyltrihydroxysilane, aminopropyltrihydroxysilane, and thiolpropyltrihydroxysilane) at a ZnO surface (0001̄) dissolved in isopropanol are studied via constant temperature (298 K) molecular dynamics simulations. The adsorbed silane molecules exhibit a different behavior depending on the chemical nature of their tail. Octyltrihydroxysilane molecules with their rather unpolar tail show two distinct, energetic different orientations at the polar metal oxide surface. Mostly the three polar hydroxy groups of the head are in contact with ZnO the unpolar tail remaining in the isopropanol phase. Occasionally only two hydroxy groups interact with the surface the whole tail simultaneously being attached. On the contrary, due to their highly polar tail aminopropyltrihydroxysilane molecules have only one favorite orientation at the surface: Apart from some minor fluctuations two hydroxy groups as well as the amino group of the tail are in contact with the surface. The behavior of the thiolpropyltrihydroxysilane molecules is somehow located in between—the thiol group is not polar enough to exhibit such a strong attraction to the polar surface to force permanent contact. Therefore, the molecules show—like octyltrihydroxysilane—two different orientations though the one similar to that of aminopropyltrihydroxysilane is slightly preferred. From adsorption energies of preferred orientations it follows that the strength of adsorption decreases from aminopropyltrihydroxysilane over thiolpropyltrihydroxysilane to octyltrihydroxysilane.

Mode of inhibition of HIV-1 reverse transcriptase by polyacetylenetriol, a novel inhibitor of RNA- and DNA-directed DNA polymerases

Polyacetylenetriol (PAT), a natural marine product from the Mediterranean sea sponge Petrosia sp., was found to be a novel general potent inhibitor of DNA polymerases. It inhibits equally well the RNA- and DNA-dependent DNA polymerase activities of retroviral reverse transcriptases (RTs) (i.e. of HIV, murine leukaemia virus and mouse mammary tumour virus) as well as cellular DNA polymerases (i.e. DNA polymerases α and β and Escherichia coli polymerase I). A study of the mode and mechanism of the polymerase inhibition by PAT has been conducted with HIV-1 RT. PAT was shown to be a reversible non-competitive inhibitor. PAT binds RT independently and at a site different from that of the primer-template and dNTP substrates with high affinity (Ki = 0.51μM and Ki = 0.53μM with dTTP and with dGTP as the variable substrates respectively). Blocking the polar hydroxy groups of PAT has only a marginal effect on the inhibitory capacity, thus hydrophobic interactions are likely to play a major role in inhibiting RT. Preincubation of RT with the primer-template substrate prior to the interaction with PAT reduces substantially the inhibition capacity, probably by preventing these contacts. PAT does not interfere with the first step of polymerization, the binding of RT to DNA, nor does the inhibitor interfere with the binding of dNTP to RT/DNA complex, as evident from the steady-state kinetic study, whereby Km remains unchanged. We assume, therefore, that PAT interferes with subsequent catalytic steps of DNA polymerization. The inhibitor may alter the optimal stereochemistry of the polymerase active site relative to the primer terminus, bound dNTP and the metal ions that are crucial for efficient catalysis or, alternatively, may interfere with the thumb sub-domain movement and, thus, with the translocation of the primer-template following nucleotide incorporation.

Mode of inhibition of HIV-1 reverse transcriptase by polyacetylenetriol, a novel inhibitor of RNA- and DNA-directed DNA polymerases.

Polyacetylenetriol (PAT), a natural marine product from the Mediterranean sea sponge Petrosia sp., was found to be a novel general potent inhibitor of DNA polymerases. It inhibits equally well the RNA- and DNA-dependent DNA polymerase activities of retroviral reverse transcriptases (RTs) (i.e. of HIV, murine leukaemia virus and mouse mammary tumour virus) as well as cellular DNA polymerases (i.e. DNA polymerases alpha and beta and Escherichia coli polymerase I). A study of the mode and mechanism of the polymerase inhibition by PAT has been conducted with HIV-1 RT. PAT was shown to be a reversible non-competitive inhibitor. PAT binds RT independently and at a site different from that of the primer-template and dNTP substrates with high affinity (K(i)=0.51 microM and K(i)=0.53 microM with dTTP and with dGTP as the variable substrates respectively). Blocking the polar hydroxy groups of PAT has only a marginal effect on the inhibitory capacity, thus hydrophobic interactions are likely to play a major role in inhibiting RT. Preincubation of RT with the primer-template substrate prior to the interaction with PAT reduces substantially the inhibition capacity, probably by preventing these contacts. PAT does not interfere with the first step of polymerization, the binding of RT to DNA, nor does the inhibitor interfere with the binding of dNTP to RT/DNA complex, as evident from the steady-state kinetic study, whereby K(m) remains unchanged. We assume, therefore, that PAT interferes with subsequent catalytic steps of DNA polymerization. The inhibitor may alter the optimal stereochemistry of the polymerase active site relative to the primer terminus, bound dNTP and the metal ions that are crucial for efficient catalysis or, alternatively, may interfere with the thumb sub-domain movement and, thus, with the translocation of the primer-template following nucleotide incorporation.

Novel Spiropiperidines as Highly Potent and Subtype Selective σ-Receptor Ligands. Part 1

A series of spiro[[2]benzopyran-1,4'-piperidines] and spiro[[2]benzofuran-1,4'-piperidines] of general structure 10 is prepared, and the affinity for sigma(1)- and sigma(2)-receptors is investigated by means of radioligand binding assays. The synthesis of the spiropiperidines 14a and 23 proceeds from bromine/lithium exchange of the bromoacetals 11 and 21, addition to piperidin-4-one 12a, and subsequent cyclization. Systematic variations of the substituent R at the nitrogen atom, the group X in position 3, and the ring size of the oxygen heterocycle are performed. The sigma(1)- and sigma(2)-receptor affinities are determined with guinea pig brain and rat liver membrane preparations using [(3)H]-labeled (+)-pentazocine and ditolylguanidine, respectively. Test results show that a benzyl residue at the piperidine nitrogen atom and a methoxy group in position 3 are advantageous for high sigma(1)-receptor affinity. In this series the 1'-benzyl-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidine] (14a) and the 1'-benzyl-3-methoxy-3H-spiro[[2]benzofuran-1,4'-piperidine] (23) are among the most potent sigma(1)-ligands interacting in the low nanomolar range with sigma(1)-receptors (14a, K(i) = 1.29 nM; 23, K(i) = 1.14 nM). Variation of the nitrogen substituent R from benzyl to H, alkyl, phenyl, or omega-phenylalkyl and the group X from methoxy to hydroxy, carbonyl, or alkyloxy led to reduced sigma(1)-receptor affinity. In addition to their high sigma(1)-receptor affinity, the spiropiperidines 14a and 23 display excellent selectivity toward sigma(2)-receptors (sigma(1)/sigma(2) = 2708 and 1130) and several other receptor and reuptake systems. Introduction of a polar hydroxy group in position 3 and elongation of the distance between the piperidine nitrogen atom and the phenyl moiety result in ligands with considerable sigma(2)-receptor affinity and therefore diminished sigma(1)/sigma(2)-receptor selectivity. The hemiacetalic 1'-(3-phenylpropyl)-3,4-dihydrospiro[[2]benzopyran-1,4'-piperidin]-3-ol (15e) represents the most active sigma(2)-receptor ligand in this series with a K(i) value of 83.1 nM.

Mode of inhibition of HIV reverse transcriptase by 2-hexaprenylhydroquinone, a novel general inhibitor of RNA-and DNA-directed DNA polymerases

A natural compound from the Red Sea sponge Ircinia sp., 2-hexaprenylhydroquinone (HPH), has been shown to be a general inhibitor of retroviral reverse transcriptases (from HIV-1, HIV-2 and murine leukaemia virus) as well as of cellular DNA polymerases (Escherichia coli DNA polymerase I, and DNA polymerases alpha and beta). The pattern of inhibition was found to be similar for all DNA polymerases tested. Thus the mode of inhibition was studied in detail for HIV-1 reverse transcriptase. HPH is a non-competitive inhibitor and binds the enzyme irreversibly with high affinity (Ki=0. 62 microM). The polar hydroxy groups have been shown to be of key importance. A methylated derivative, mHPH, which is devoid of these polar moieties, showed a significantly decreased capacity to inhibit all DNA polymerases tested. Like the natural product, mHPH binds the enzyme independently at an allosteric site, but with reduced affinity (Ki=7.4 microM). We show that HPH does not interfere with the first step of the polymerization process, i.e. the physical formation of the reverse-transcriptase-DNA complex. Consequently, we suggest that the natural inhibitor interferes with the subsequent steps of the overall reaction. Since HPH seems not to affect the affinity of dNTP for the enzyme (the Km is unchanged under conditions where the HPH concentration is increased), we speculate that its inhibitory capacity is derived from its effect on the nucleotidyl-transfer catalytic reaction. We suggest that such a mechanism of inhibition is typical of an inhibitor whose mode of inhibition should be common to all RNA- and DNA-directed polymerases.

Accumulation of lipid peroxidation products in human cataracts.

The role of free-radical-induced lipid peroxidation (LPO) in the development of human lens opacity was investigated. 130 human crystalline lenses impaired with cataract of various etiology (senile, traumatic, complicated cataracts) at different stages of cataract development as well as 18 transparent human lenses were studied. Primary products of LPO (diene conjugates), secondary products (ketodienes) and the end products (Schiff bases) were distinctly accumulated in cataractous lenses. Initial stages of cataract were characterized by the accumulation of primary LPO products, while in the latest stages there was a prevalence of fluorescent end products of LPO. It was concluded that the accumulation of polar hydroxy groups in the lipid bilayer of plasma membranes of lenticular fibers is one of the possible causes of their injury in cataracts.

ESR–ENDOR studies of x-irradiated glucose-1-phosphate dipotassium salt

Single crystals of the dipotassium salt of gluocose-1-phosphate were grown out of water or deuterium oxide and x-irradiated at 4.2 °K. The products of irradiation were identified by means of ESR and ENDOR spectroscopy. In crystals grown out of water, three different alkoxy radicals were observed as oxidation products. In partially deuterated crystals only one of the aforementioned alkoxy radicals was produced. A hydroxyalkyl radical, RHĊOH was also produced by loss of hydrogen from the C6′ position. Electrons trapped at intermolecular sites were identified. The distances between the electron and the protons of the polar hydroxy groups forming the trap were deduced from ENDOR measurements and found to be relatively large, namely 1.732 and 1.738 Å.

The nature of physical adsorption of surface-active cations of some organic inhibitors of acid corrosion of metals

The central atom of each of these surface-active cations, which confers their adsorption properties on them, is the nitrogen atom. The coordination valence of cationic nitrogen in N-substituted pyridine compounds is four, and the nitrogen atom carries practically the entire positive charge of the ion. The magnitude of this charge, which determines the adsorptive power of organic cations and, consequently, their surface-active properties, depends on the affinity of the substituting components (radicals and functional groups) to electrons, on the proneness of these components to ~-electron coupling, and on the place of substitution. Owing to the electro-affinity effect, electrons in the pyridine center are displaced toward the nitrogen atom [2-4], so that the negative charge density near this atom is larger than in other regions of the aromatic ring. The displacement of pyridine cation electrons is intensified by the positive charge produced in the nitrogen atom as a result of the coupling of its unshared electron pair with the N-substituting radical-cation [5-7]. For both these reasons, electrons in the pyridine center are strongly drawn toward the nitrogen atom. The n- and ~r-electron coupling, the difference in the affinity to electrons, and the establishment of a double virtual bond [8], all cause migration of electrons from the substituting groups to the pyridine center. Consequently, the substituting groups determine both the magnitude of the positive charge of the nitrogen atom in pyridine cations and the polarizability of the cation in the electric field of a metal surface, i.e., they determine its adsorbability. In respect to their affinity to electrons, radicals and groups form a series in which -CHa < -OH [6, 9, 10]. The affinity of the phenyl radical to electrons is higher than that of the methyl radical, so that the latter confers a negative charge on a benzene ring [6, 11, 12] as a result of which a certain dipole moment is produced in a toluene molecule [6, 13, 14]. A similar relation between affinities is indicated by the effect of these and several other substitutes in the 2-, 3-, and 4-positions on the basic properties of pyridine [3]. Since the electron affinity of the phenyl radical is higher than that of the hydroxy group (see the properties of phenyl [3, 7, 9, 13-17], the affinity series may be extended: -CH 3 < -OH < -C6H 5, It is known [2, 3, 7, 10, 14-18], that the -OH group in aromatic compounds serves as a donor of electrons, the aromatic radical intensifying the acid properties of this group, whereas in alkyl compounds (alcohols), for instance, this group acts as an acceptor of electrons (with hydrocarbon groups and, mainly, the methyl CHs-grou p acting as donors) and is weakly acidic in character. The donor properties of the hydroxy group are markedly pronounced even in phenyl, in which the n-electrons of oxygen become coupled with the ~r-electrom of the aromatic center. As a result of this coupling, oxygen becomes positively charged which, in turn, increases the probability of protons being detached from oxygen atoms. When the -OH group is fully ionized, the negative ionic charge of a phenolate ion extends over the entire coupling system, as a result of which the negative charge of oxygen is reduced and so is, consequently, the tendency of the phenolate ion to recombine with the proton. The processes under review are also affected by the fact that the ionization of phenyl molecules is strongly dependent on the pH of the medium: The first signs of ionization are observed at pH = 6, and it becomes complete at pH = 11.8 [19]. This is in agreement with the fact [20] that phenyl (dissolved in ethyl alcohol which behaves as a base in respect to phenyl) is more strongly adsorbed than benzene on charged mercury surfaces. It shifts the zero charge potential more strongly toward the negative potential values, reduces the electrocapillary maximum more strongly, and is more readily desorbed from negatively charged mercury surfaces than benzene which, naturally, is associated with the presence in the molecule of a polar hydroxy group. A similar phenomenon is observed in aqueous solutions of sulfuric acid [21]. When the -OH group is introduced into an aromatic center, the adsorbability of aromatic compounds on positively charged metal surfaces increases in the order benzene-phenyl-r esorcin, the shift of the zero charge potential toward negative values increasing, and adsorbability on negatively charged metal surfaces decreasing, in the same order.