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This article provides a detailed account of the synthesis and characterization of pyridinium salts derived from hydroxymethyl-containing compounds. The researchers conducted bioactivity tests on the synthesized salts and found that some of them exhibited strong antimicrobial activity against bacteria and fungi. The study suggests that these salts have the potential to be developed into new antimicrobial drugs, but further research is needed to fully explore their properties. The research was conducted by scientists from Kazan Federal University and Kazan State Medical Academy in Russia. [Extracted from the article]

In this study, perthiophosphonic acid anhydrides which are previously known (2,4-bis(3-methoxytolyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide ([(3-methoxytolyl)P(S)S)2], SAV-B1 reagent and 2,4-bis(ferrocenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide [(ferrocenyl)P(S)S)2], FcLR, Ferrocenyl Lawesson's Reagent) react with alcohols to obtain new dithiophosphonic acids (3-methoxytolyl=(CH3)(OCH3)C6H3- and Xn=alkyl group (R) for SAV-B1, HXn; R1=3-pentyl-, HX1; R2=2-butyl-, HX2; R3=2-pentyl-, HX3 and Fc=Ferrocenyl- and Yn=allkyl or aryl group (R’) for FcLR, HYn; R’1=4-tert-cyclohexyl-, HY1; R’2=2-phenyl-1-propyl-, HY2). These acids were then converted to ammonium salts ([NH4][Xn], [NH4][Yn]). The structures of ammonium salts were characterized by mass-(ESI), FT-IR, 1H-, 13C- and 31P-NMR spectroscopy and elemental analysis.

In this study, perthiophosphonic acid anhydrides which are previously synthesized (2,4-bis(3-methoxytolyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide ([((3-methoxytolyl) P(S)S)2], SAV-B1 reagent and 2,4-bis(ferrocenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide [((ferrocenyl)P(S)S)2], FcLR, Ferrocenyl Lawesson's Reagent) react with alcohols to obtain new dithiophosphonic acids (3-methoxytolyl=(CH3)(OCH3)C6H3- and Xn=Alkyl group (R) for SAV-B1, HXn; R1=3-pentyl-, HX1; R2=2-butyl-, HX2; R3=2-pentyl-, HX3 and Fc=Ferrocenyl- and Yn=Alkyl or aryl group (R') for FcLR, HYn; R'1=4-tert-cyclohexyl-, HY1; R'2=2-phenyl-1-propyl-, HY2). These products were later transformed into their ammonium salts ([NH4][Xn], [NH4][Yn]). The structures of ammonium salts were characterized by mass, FT-IR, ¹H-, 13C- and 31P-NMR spectroscopy and elemental analysis. [ABSTRACT FROM AUTHOR]

In this work, thermodynamic properties (Heat capacity, Entropies, Enthalpy, Gibbs free and Thermal energy) and frontier (HOMO, LUMO) molecular orbitals of a derivative dithiophosphonates molecule which is [+HN(C2H5)3][CH3CHOC6H3(CF3)2)(CH3OC6H4)PS2-] in the ground state were calculated by using the quantum chemical calculation method such as density functional theory (DFT) employing B3LYP and HF levels with the 6-31G(d) basis set. In addition, the frontier molecular orbitals analysis of the molecule were researched using computational methods. Properties about the charge density distribution of the title compound and its chemical reactivity has been investigated with mapping molecular electrostatic potential surface. [ABSTRACT FROM AUTHOR]

Abstract Five new dithiophosphonic acids ((p -MeO-C 6 H 4)PS(SH)(OR), HLn, (n = 1–5); R = 3-pentyl-, HL1; R = 1-phenyl-1-propyl-, HL2; R = 4-tert-butyl benzyl-, HL3; R = diphenylmethyl-, HL4; R = 4-tert-butylcyclohexyl-, HL5) were prepared by the reaction of Lawesson reagent with the corresponding alcohols. As the acids were viscous liquids and difficult to purify they were converted to their ammonium salts ([NH 4 Ln]) for purification through crystallization. Four coordinated Ni(II) complexes of the dithiophosphonates ([Ni(Ln) 2 ]) were synthesized in methanol medium and purified. The reaction between these square planar complexes and pyridine was carried out to produce six coordinated pyridine derivatives ([Ni(Ln) 2 (py) 2 ]). The structures of the fifteen compounds so prepared were elucidated by spectroscopy, elemental analysis methods and magnetic susceptibility measurement. The molecular and crystal structure of [Ni(L2) 2 (py) 2 ] was determined by X-ray crystallography. DFT calculations were carried out using the B3LYP functional with the LANL2DZ basis set to the optimized geometrical structure and determine the energies, the orientations of the molecular orbitals (HOMOs and LUMOs) and the molecular electrostatic potential (MEP) surfaces of the octahedral complex [Ni(L2) 2 (py) 2 ]. The results for [Ni(L2) 2 (py) 2 ] revealed that these bonded to the active sites of A-DNA and B-DNA by weak non-covalent interactions, which was also supported by molecular docking investigations. Graphical abstract Image 1 Highlights • 5 new dithiophosphonate-type ligands and 5 Ni-complexes were prepared. • Nickel complexes were further reacted with pyridine to obtain 5 new octahedral pyridine complexes. • Elemental analyses and spectroscopic characterizations of the compounds were elucidated. • X-ray structure analysis, DFT studies and molecular docking one of the 5 pyridine nickel complex were done. [ABSTRACT FROM AUTHOR]

A novel metal-organic planar NiS 4 - type complex, trans - Ni(II)-bis[O-(2-butoxyethyl)-(4-methoxyphenyl)dithiophosphonate], was synthesized by the reaction of ammonium salt of O-dithio phosphonic acid with Ni(CH 3 COO) 2 . The crystal structure of Ni(II)-complex was determined by X-ray Diffraction (XRD) analysis. As a result of the X-ray crystal and molecule structure analyses of the studied trans - Ni(II)-complex, it was obtained that the central nickel atom is coordinated by four sulphur atoms in slightly distorted a square-planar geometry. The X-ray structure confirms a trans isomer of the Ni(II)-complex. The Ni(II)-complex crystallizes in the monoclinic space group C12/c1 with unit cell parameters a 22.376(3) (Å), b 18.466(3) (Å) and c 8.6875(13) (Å). In addition, theoretical calculations with the basis set of B3LYP/6-311 + G(2d,p) are performed to determine the structural properties, FT-IR, NMR spectrum, electronic properties and NBO analysis of the compound. The experimental and computed results of the Ni(II)-complex were found to be in good agreement. [ABSTRACT FROM AUTHOR]

Chiral S‐tributylstannyl dithiophosphates and dithiophosphonates were obtained by the reactions of optically active dithiophosphoric and dithiophosphonic acids containing (S)‐(–)‐menthyl and (R)‐(+)‐menthyl substituents with gaseous ammonia and tributyl chlorostannane. The reactions of chiral ammonium dithiophosphate containing (1R)‐endo‐(+)‐fenchyl substituent with tributyl chlorostannane or tetrachlorostannane result in corresponding S‐tributylstannyl dithiophosphate or tetrakis(dithiophosphato)stannane. Molecular structure of ammonium O,O‐di‐(–)‐menthyldithiophosphate was studied by X‐ray single crystal diffraction. Bactericidal activity of S‐tributylstannyl dithiophosphates was tested. [ABSTRACT FROM AUTHOR]

The reaction of ammonium salts of benzylferrocenyldithiophosphonate ligands [NH 4 ][S 2 P(OR)(Fc)] [R = Bz ( 1 ), 4-( i Pr)-Bz ( 2 ), 4-( t Bu)-Bz ( 3 ), 4-(Ph)-Bz ( 4 ), 3-(OBz)-Bz ( 5 ); Bz = benzyl, Fc = ferrocenyl] with organotin(IV) chlorides Ph 2 SnCl 2 , n Bu 2 SnCl 2 and Ph 3 SnCl, gave the corresponding organotin(IV) benzylferrocenyldithiophosphonates [Ph 2 Sn{S 2 P(OR)(Fc)} 2 ] [R = Bz ( 6 ), 4-( i Pr)-Bz ( 7 ), 4-( t Bu)-Bz ( 8 ), 4-(Ph)-Bz ( 9 ), 3-(OBz)-Bz ( 10 )], [ n Bu 2 Sn{S 2 P(OR)(Fc)} 2 ] [R = Bz ( 11 ), 4-(Ph)-Bz ( 12 )] and [Ph 3 Sn{S 2 P(OBz)(Fc)}] ( 13 ). Compounds 6 – 13 were characterized by elemental analyses, infrared, 1 H, 13 C{ 1 H}, 31 P{ 1 H} and 119 Sn{ 1 H}NMR spectroscopy and ESI mass spectrometry, while complexes 6 , 11 and 13 were also characterized by single-crystal X-ray diffraction studies. The dithiophosphonate ligands display an anisobidentate coordination mode upon interaction with the metal center. The solid-state structures of the disubstituted complexes 6 and 11 exhibit a trans arrangement for the ferrocenyl groups from the dithiophosphonate ligands. [ABSTRACT FROM AUTHOR]

• 2,4- bis (2,4-dimethoxyphenyl)−1,3-dithia-2,4-diphosphetane 2,4-disulfide and its derivatives were synthesized and characterized for the first time. • Single crystal X-ray diffraction analysis and theoretical studies of the Ni(II) complex was performed. • In vitro cytotoxic activities of the compounds were studied. New 2,4- bis (2,4-dimethoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, (SAV-A2), was synthesized from the reaction P 4 S 10 and 1,3-dimethoxybenzene. SAV-A2 was reacted with alcohols to form dithiophosphonic acid monoesters (HLn, HS 2 P((2,4-CH 3 O) 2 C 6 H 3)(ORn); n =1–3, R1=2‑butyl‑; R2= n -pentyl-; R3= 4‑tert ‑but-benzyl-). The acids were converted to the ammonium salts ([NH 4 L n ]) to serve as the source of the ligands (Ln), to obtain Ni(II) complexes, ([N i (L n) 2 ]). [Ni(L2) 2 ] crystal structure was elucidated by single-crystal X-ray diffraction analysis. In addition, Density Functional Theory (DFT) calculations of [Ni(L2) 2 ] was performed. The molecular docking studies of the complex with liver cancer protein, PDB ID: 3WZE and colon cancer antigen proteins, ID 2HQ6 were done compare with experimental and theoretical results. All compounds were tested on liver- and colon cancer cell lines. Among the complexes tested, [Ni(L3) 2 ] showed an activity closer to that of cisplatin against the colon cancer cell line. The other compounds were found to be have less active. [Display omitted] [ABSTRACT FROM AUTHOR]

• Self-assembly of the dithiophosphonate tectons generating supramolecular synthons via N H···S, N H···O, C H···S, C H···O, C H···π, and lp···π interactions. • Connection between molecular and supramolecular chirality in the crystalline state (chirogenesis). • NCI index analysis supports the proposition of P-stereogenic centers. • Chiral transference of the p atom to the supramolecular helical assembly. • Spontaneous resolution process to generate the homochiral crystal. The self-assembly of the dithiophosphonate tectons synthesized in this work generated novel supramolecular synthonsvia N H···S, N H···O, C H···S, C H···O, C H···π, and lp···π interactions. The reaction of the salts with chloro dithiastibocanes X(CH 2 CH 2 S) 2 SbCl (X = O , S) led to the formation of coordination compounds in which the crystal structures showed two new supramolecular synthons stabilized by C H···π and lp···π interactions. The theoretical study of the electronic density of the crystal and their synthons in the solid-state used the robust NCI index to confirm the nature of the interactions found. This study confirmed the connection between molecular and supramolecular chirality in the crystalline state. Three significant features unequivocally support the findings: the role of intramolecular interactions, the electronic density differences among diastereomers, and the nature of trans-annular bonds. The characterization of the salts: ammonium-menthoxy (4-methoxyphenyl) dithiophosphonate (1), triethylammonium-menthoxy (4-methoxyphenyl)-dithiophosphonate (2), triethylammonium-biphenyl-4‑methoxy (4-methoxyphenyl) dithiophosphonate (3), and the coordination compounds O(CH 2 CH 2 S) 2 Sb[S 2 P(biphenyl-4‑methoxy)(4-MeOC 6 H 4)] (4) and S(CH 2 CH 2 S) 2 Sb[S 2 P(biphenyl-4‑methoxy)(4-MeOC 6 H 4)] (5) was carried out by elemental analyses, IR, NMR (1H, 13C, 31P), and single-crystal X-ray diffraction analysis. [Display omitted] [ABSTRACT FROM AUTHOR]

Facilitated transport of Ni(ll) ions across a supported liquid membrane (SLM) by dithiophosphonates dissolved in methanol as carrier has been investigated. In this work, the SLMs were composed of ionic ligands ammonium-O-ethyl (4-methoxyphenyl) dithiophosphonate (LI), ammonium-O-propyl (4-methoxyphenyl) dithiophosphonate (L2), ammonium-O-isopropyl (4-methoxyphenyl) dithiophosphonate (L3), and ammonium-O-butyl (4-methoxyphenyl) dithiophosphonate (L4) as the carriers. Polyvinylidene fluoride (PVDF) hydrophobic microporous membrane was used as support. The experiments were carried out at various operating conditions such as feed phase pH, receiver phase concentration, carrier concentration in the membrane phase, different valence metal ion, and SLM stability. The morphology of SLMs was characterized using scanning electron microscopy (SEM), atomic force microscopy (AFM), andfourier transform infrared spectroscopy (FTIR). The SEM, AFM, ami FTIR images, comparing the PVDF membrane support to SLMs, indicate that the surface morphologies of the membranes are different. The flux values (J) and recovery factors (RF) of Ni(II) ions were obtained at optimum pH 2. Similar flux results were obtained for all SLMs at optimum condition and in a period of 8 h. Increase in carrier concentration inside the membrane enhances Ni(II) concentration with its maximum value at 4.0 x 10-1 mol/L carrier. [ABSTRACT FROM AUTHOR]

The reaction of benzylferrocenyldithiophosphonate ligands [NH 4 ][S 2 P(OR)(Fc)] [R = Bz ( 1 ), 4-( i Pr)-Bz ( 2 ), 4-( t Bu)-Bz ( 3 ), 4-(Ph)-Bz ( 4 ), 3-(OBz)-Bz ( 5 ); Bz = benzyl, Fc = ferrocenyl] with organotellurium iodides, C 4 H 8 TeI 2 and C 8 H 8 TeI 2 , yielded the corresponding tellurium(IV) dithiophosphonate complexes [C 4 H 8 Te{S 2 P(OR)(Fc)} 2 ] [R = Bz ( 6 ), 4-( i Pr)-Bz ( 7 ), 4-( t Bu)-Bz ( 8 ), 4-(Ph)-Bz ( 9 ), 3-(OBz)-Bz ( 10 )] and [C 8 H 8 Te{S 2 P(OR)(Fc)} 2 ] [R = Bz ( 11 ), 4-( i Pr)-Bz ( 12 ), 4-( t Bu)-Bz ( 13 ), 4-(Ph)-Bz ( 14 ), 3-(OBz)-Bz ( 15 )]. Compounds 6 – 15 were characterized by elemental analyses, infrared, 1 H, 13 C, 31 P and 125 Te NMR spectroscopy and EI mass spectrometry, while complexes 6 , 11 and 14 were also characterized by single-crystal X-ray diffraction studies. The dithiophosphonate ligands display an anisobidentate coordination mode upon interaction with the metal center. The solid-state structures show ferrocenyl groups in the dithiophosphonate ligands adopting trans arrangements. [ABSTRACT FROM AUTHOR]

Background: The novel amido and O-ferrocenyldithiophosphonates [FcP(S)(SH)(NHR¹)] (Fc = Fe(η5-C5H5)(η5-C5H4), R¹ = 1-(4-fluorophenylethyl and benzyloxycyclopentyl) and [FcP(S)(OR²)S-][H3N+C(CH3)3] (R² = myrtanyl) were synthesized by the reaction of [(FcPS2)]2 (Fc = Fe(η5-C5H5)(η5-C5H4)) and chiral amines, such as (S)-(–)-1-(4-fluorophenylethyl) amine and (1S,2S)-(+)-benzyloxycyclopentyl amine, and of (1S), (2S), (5S)-myrtanol in toluene. The reaction of ferrocenyldithiophosphonates and [Cu(PPh3)2]NO3 or AgNO3 and PPh3 gave rise to copper(I) and silver(I) complexes in THF. [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 were embedded into nanofibers and their antimicrobial activities on fibers were also investigated. Results: The compounds have been characterized by elemental analyses, IR, NMR (¹H-, 31P-) spectroscopy as well as MS measurements. Nanofibers were obtained by electrospinning method which is the simplest and most effective method to produce nanoscale fibers under strong electrical field. Antimicrobial activity of the compound 5, [Ag2{FcP (OMe)S2}2(PPh3)2], and [Cu(PPh3)2]NO3 on fibers were studied. Conclusions: In this study, the new dithiophosphonate ligands were synthesized and utilized in the preparation of copper(I) and silver(I) complexes with ferrocenyldithiophosphonate and triphenylphosphine. Then, the compounds [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 were added into the PAN solutions (Co-PAN dissolved in dimethylacetamide) and the solutions were electrospun onto microscope slides and PP meltblown surfaces. Antimicrobial activity of the compounds [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 on fibers were determined in vitro against two indicator strains; M. luteus NCIB and E. coli ATCC25922. The obtained results indicated that these metals showed moderate level antimicrobial activities. [ABSTRACT FROM AUTHOR]

A new series of dithiophosphonates has been synthesized using cycloiminium halides of pyridine, thiazole, and benzothiazole as starting material, dichlorophenylphosphine as phosphorylating agent, and 2-propanethiol as nucleophilic substituent. These compounds were tested for their insecticidal activity against a polyphagous insect plutella xylostella and found to exhibit potent pesticidal activity. [ABSTRACT FROM AUTHOR]

2,4-Bis-(4-methoxyphenyl)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) reacts with a variety of alcohols and silanols to form dithiophosphonic acids in a facile manner. Their lithium salts react with organotin- and organogermanium chlorides to produce organometallic dithiophosphonate complexes of the type A R3"M[S(S)P(R)(OR')] (M = Ge, Sn; R = 4-MeOC6H4; R' = Me, SiPh3, GePh3, SnPh3; R'' = Me, Ph) and B R2"M[S(S)P(R)(OR')]2 (M = Ge, Sn; R = 4-MeOC6H4; R' = Me, Et, iPr, tBu, SiPh3; R'' = Me, Ph). The ligands in the new organometallic compounds are bound in an asymmetric fashion as revealed by four X-ray structure determinations, containing one representative example of type A and three examples of type B. All new compounds are fully characterized by analytical and spectroscopic methods. [ABSTRACT FROM AUTHOR]

The transport of Cu(II) ions from an aqueous solution into an aqueous receiving solution through a bulk liquid membrane containing a dithiophosphonate derivative (1) as a carrier was examined. The kinetic parameters were analyzed assuming 2 consecutive, irreversible first-order reactions. The influence of temperature and stirring rate on the kinetic parameters (k1, k2 Rmmax, tmax, Jdmax and Jamax) was also investigated. The membrane entrance rate, k1, and the membrane exit rate, k2 increased with increasing temperature and stirring rate. For the maximum membrane exit flux, Jamax, the activation energy was determined from the slope of the linear Arrhenius relationship to be 8.70 kcal mol-1, which indicates that the process is controlled by species diffusion. [ABSTRACT FROM AUTHOR]

• One-step synthesis of a new phosphine-phosphonodithioate ligand. • Minor Zwitterionic byproduct obtained and verified by X-ray diffraction. • Ligand uses both P- and S/S-donor sites to bind identical metal centres. • Solution and solid-state structures confirmed using NMR and single crystal XRD. Reaction of Ph 2 PCH 2 OH and {RP(S)(μ-S)} 2 (R = p -C 6 H 4 OMe, Lawesson's reagent), in toluene, gave the new hybrid PIII/PV ligand Ph 2 PCH 2 OP(S)(R)SH 1 in high yield. Unfortunately, attempts to crystallise 1 gave, instead, suitable X-ray quality crystals of the Zwitterion Ph 2 P+(CH 2 OH)CH 2 OP(S)(R)S− 1 ′, presumably arising from the presence of some residual formaldehyde. Three homodinuclear complexes [Ru 2 (η6- p -CH 3 C 6 H 4 i Pr) 2 {μ-Ph 2 PCH 2 OP(S)(R)S}Cl 3 ] (2) and [M 2 (η5-C 5 (CH 3) 5) 2 {μ-Ph 2 PCH 2 OP(S)(R)S}Cl 3 ] [M = Rh, 3 ; M = Ir, 4 (R = p -C 6 H 4 OCH 3)] were obtained upon reaction of a 1:1 molar ratio of 1 and either [(η6- p -CH 3 C 6 H 4 i Pr)RuCl(μ-Cl)] 2 or [M(μ-Cl)(Cl)(η5-C 5 (CH 3) 5) 2 ] 2 (M = Rh and Ir), respectively. The mononuclear IrIII complex Ir(η5-C 5 (CH 3) 5)(Ph 2 PCH 2 OH)Cl 2 5 was prepared for comparative spectroscopic and crystallographic purposes with 4. All compounds were characterised by a combination of multinuclear NMR and FT−IR spectroscopy and elemental analysis. In addition, the first example of a phosphine-dithiophosphonate ligand 1 ′ along with two homodinuclear complexes 2 ·CHCl 3 and 4 were determined by single crystal X-ray diffraction. Compound 5 displays an intramolecular O(1)−H(1)···Cl(2) hydrogen bond to a terminal IrIII bound chloride ligand. Image, graphical abstract [ABSTRACT FROM AUTHOR]