Pub Date : 2023-08-10DOI: 10.1080/10426507.2023.2242995
H. Akbaş, Ayşegül Şenocak, Z. Kılıç, Seçil Erden Tayhan, Sema Bilgin, Aslı Yıldırım Kocaman, T. Hökelek
Abstract In this study, the condensation reaction of hexachlorocyclotriphosphazene, N3P3Cl6 (HCCP) with N 1,N3 -bis(furan-2-ylmethyl)-1,3-diamino-propane (1) yielded tetrachlorobis(2-furanyl-methyl)monospiro(N/N)cyclotriphosphazene (2). Fully substituted tetraaminobis(2-furanylmethyl)-spiro(N/N)cyclotriphosphazenes (2a and 2b) were obtained by Cl replacement reactions with excess pyrrolidine and piperidine, respectively, using dry THF under reflux of 2. The structures of the phosphazenes were confirmed by data obtained by elemental analysis, FT-IR, ESI-MS, 1H, 13C, and 31P NMR. Moreover, the molecular structure of 2b was elucidated by X-ray crystallography. The antiproliferative effects of phosphazenes (2, 2a, and 2b) on prostate (PC-3) and colon cancer (HT-29) cell lines were determined by cell viability analysis using MTT assay. Antimigratory effects were also investigated by scratch analysis. In addition, the effects of compounds against genes involved in apoptosis and cell migration were evaluated by gene expression analysis. As a result, it was found that compound 2a was more effective than compound 2b in both prostate and colon cancer cell lines. GRAPHICAL ABSTRACT
{"title":"Bis(2-furanylmethyl)monospiro(N/N)cyclotriphosphazenes: synthesis, structural characterization, antiproliferative, and antimigratory activity studies","authors":"H. Akbaş, Ayşegül Şenocak, Z. Kılıç, Seçil Erden Tayhan, Sema Bilgin, Aslı Yıldırım Kocaman, T. Hökelek","doi":"10.1080/10426507.2023.2242995","DOIUrl":"https://doi.org/10.1080/10426507.2023.2242995","url":null,"abstract":"Abstract In this study, the condensation reaction of hexachlorocyclotriphosphazene, N3P3Cl6 (HCCP) with N 1,N3 -bis(furan-2-ylmethyl)-1,3-diamino-propane (1) yielded tetrachlorobis(2-furanyl-methyl)monospiro(N/N)cyclotriphosphazene (2). Fully substituted tetraaminobis(2-furanylmethyl)-spiro(N/N)cyclotriphosphazenes (2a and 2b) were obtained by Cl replacement reactions with excess pyrrolidine and piperidine, respectively, using dry THF under reflux of 2. The structures of the phosphazenes were confirmed by data obtained by elemental analysis, FT-IR, ESI-MS, 1H, 13C, and 31P NMR. Moreover, the molecular structure of 2b was elucidated by X-ray crystallography. The antiproliferative effects of phosphazenes (2, 2a, and 2b) on prostate (PC-3) and colon cancer (HT-29) cell lines were determined by cell viability analysis using MTT assay. Antimigratory effects were also investigated by scratch analysis. In addition, the effects of compounds against genes involved in apoptosis and cell migration were evaluated by gene expression analysis. As a result, it was found that compound 2a was more effective than compound 2b in both prostate and colon cancer cell lines. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"77 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73846742","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-08-02DOI: 10.1080/10426507.2023.2240933
Yalin Fan, Dan Wang, Liang Wang
Abstract A facile sulfonylation of activated alkenes employing sodium arylsulfinates in Brønsted acidic deep eutectic solvent at room temperature has been developed. The choline chloride/p-toluenesulfonic acid deep eutectic solvent acts both the solvent and as the catalyst, affording the desired γ-keto sulfones in good yields. Easily accessible starting materials, good functional group compatibility as well as simple recovery of the solvent make this procedure environmentally benign. Graphical Abstract
{"title":"Synthesis of γ-keto sulfones via sulfa-Michael reactions in Brønsted acidic deep eutectic solvent","authors":"Yalin Fan, Dan Wang, Liang Wang","doi":"10.1080/10426507.2023.2240933","DOIUrl":"https://doi.org/10.1080/10426507.2023.2240933","url":null,"abstract":"Abstract A facile sulfonylation of activated alkenes employing sodium arylsulfinates in Brønsted acidic deep eutectic solvent at room temperature has been developed. The choline chloride/p-toluenesulfonic acid deep eutectic solvent acts both the solvent and as the catalyst, affording the desired γ-keto sulfones in good yields. Easily accessible starting materials, good functional group compatibility as well as simple recovery of the solvent make this procedure environmentally benign. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"108 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80807414","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-20DOI: 10.1080/10426507.2023.2235054
D. Moiseev
Abstract Secondary phosphine oxides R2P(O)H are a relatively stable tautomeric form of secondary phosphinous acids R2P–OH that with imine/iminium species, or their donors, form compounds with a P(O)–C sp3 –N linkage (the phospha-Mannich reaction). These can be referred to as (α-aminoalkyl)phosphine oxides, (α-phosphinoylalkyl)amines, or P(O),N-acetals. Compared to P–C sp3 –N linkages of P,N-acetals, products of phospha-Mannich reactions involving secondary phosphines R2PH, the P(O)–C sp3 –N linkage is significantly more stable that allows for many examples of α-functionalized P(O),N-acetals and α-phosphinoylated N-heterocycles, whereas such examples for P,N-acetals are rare. Trivalent derivatives of phosphinous acids such as halides R2P–Hal, esters R2P–OR’ (phosphinites), amides R2P–NR’2 (aminophosphines), and phosphides R2P–PR’2 (biphosphines) also participate in Mannich-type reactions with mechanisms depending on the reactants. The phosphinous halides and esters react with (α-alkoxyalkyl)amines (N,O-acetals) and (α-haloalkyl)amines (N,Hal-acetals), respectively, via Arbuzov-type intermediates that are rearranged into P(O),N-acetals and alkyl halides (Arbuzov rearrangement). Furthermore, unlike phospha-Mannich reactions involving phosphines, secondary phosphine oxides and P(O),N-acetals are less sensitive to oxidation, and imines/iminium species can be generated not only under conventional Mannich conditions, i.e., from N,E-acetals (E = OH, O, N, halogen, etc.), but also, for example, by oxidation of α-C-atom of amines, or by oxidation of alcohols to aldehydes that than form imines/iminium species with amines. Graphical abstract
{"title":"Phospha-Mannich reactions of phosphinous acids R2P–OH and their derivatives","authors":"D. Moiseev","doi":"10.1080/10426507.2023.2235054","DOIUrl":"https://doi.org/10.1080/10426507.2023.2235054","url":null,"abstract":"Abstract Secondary phosphine oxides R2P(O)H are a relatively stable tautomeric form of secondary phosphinous acids R2P–OH that with imine/iminium species, or their donors, form compounds with a P(O)–C sp3 –N linkage (the phospha-Mannich reaction). These can be referred to as (α-aminoalkyl)phosphine oxides, (α-phosphinoylalkyl)amines, or P(O),N-acetals. Compared to P–C sp3 –N linkages of P,N-acetals, products of phospha-Mannich reactions involving secondary phosphines R2PH, the P(O)–C sp3 –N linkage is significantly more stable that allows for many examples of α-functionalized P(O),N-acetals and α-phosphinoylated N-heterocycles, whereas such examples for P,N-acetals are rare. Trivalent derivatives of phosphinous acids such as halides R2P–Hal, esters R2P–OR’ (phosphinites), amides R2P–NR’2 (aminophosphines), and phosphides R2P–PR’2 (biphosphines) also participate in Mannich-type reactions with mechanisms depending on the reactants. The phosphinous halides and esters react with (α-alkoxyalkyl)amines (N,O-acetals) and (α-haloalkyl)amines (N,Hal-acetals), respectively, via Arbuzov-type intermediates that are rearranged into P(O),N-acetals and alkyl halides (Arbuzov rearrangement). Furthermore, unlike phospha-Mannich reactions involving phosphines, secondary phosphine oxides and P(O),N-acetals are less sensitive to oxidation, and imines/iminium species can be generated not only under conventional Mannich conditions, i.e., from N,E-acetals (E = OH, O, N, halogen, etc.), but also, for example, by oxidation of α-C-atom of amines, or by oxidation of alcohols to aldehydes that than form imines/iminium species with amines. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"13 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80654195","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-12DOI: 10.1080/10426507.2023.2232920
I. V. Svistunova, A. Gerasimenko, M. A. Zavodianskii
Abstract The molecular and crystal structure of boron difluoride acetylacetonates containing selenophenyl (1), diselenide (2) and selenocyanate groups (3) at the central carbon atom (γ) has been determined. As a result of comparing the structure of selenium- and sulfur-substituted complexes, it is shown that the replacement of a sulfur atom with a selenium atom practically does not change the relative position of substituents and chelate cycles, as well as the values of the main angles. The packing of complexes 2 and 3 in crystals repeats the packing of sulfur-containing analogues. For phenyl-substituted selenide and sulfide, the crystals are not isostructural. In the diselenide complex 2 molecules crystallize in pairs with one chelate cycle of each molecule participating in pair formation. The pairs are linked by an interaction similar to the stacking interaction. The second chelate cycle of each molecule in the pair does not participate in intermolecular interactions. In the acetylacetonate complexes studied, the chelate rings are not planar. These cycles have a “boat” conformation. The magnitude of bending of the cycle is determined by intermolecular interactions. GRAPHICAL ABSTRACT
{"title":"Crystal structure of selenium-substituted acetylacetonates of boron difluoride","authors":"I. V. Svistunova, A. Gerasimenko, M. A. Zavodianskii","doi":"10.1080/10426507.2023.2232920","DOIUrl":"https://doi.org/10.1080/10426507.2023.2232920","url":null,"abstract":"Abstract The molecular and crystal structure of boron difluoride acetylacetonates containing selenophenyl (1), diselenide (2) and selenocyanate groups (3) at the central carbon atom (γ) has been determined. As a result of comparing the structure of selenium- and sulfur-substituted complexes, it is shown that the replacement of a sulfur atom with a selenium atom practically does not change the relative position of substituents and chelate cycles, as well as the values of the main angles. The packing of complexes 2 and 3 in crystals repeats the packing of sulfur-containing analogues. For phenyl-substituted selenide and sulfide, the crystals are not isostructural. In the diselenide complex 2 molecules crystallize in pairs with one chelate cycle of each molecule participating in pair formation. The pairs are linked by an interaction similar to the stacking interaction. The second chelate cycle of each molecule in the pair does not participate in intermolecular interactions. In the acetylacetonate complexes studied, the chelate rings are not planar. These cycles have a “boat” conformation. The magnitude of bending of the cycle is determined by intermolecular interactions. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"102 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85828195","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-12DOI: 10.1080/10426507.2023.2232509
A. Tan, Aytekin Köse, D. Mete, Gülşah Şanlı‐Mohamed, Nurhan Kishali, Yunus Kara
Abstract This study aims to evaluate the synthesis of isoindole-1,3-dione analogues and their cytotoxic potential. A549 and HeLa cells exposed to 250–100–50–25 µM doses of each derivative were incubated for 24, 48, and 72 h. The cytotoxicity of the isoindole-1,3-dione derivatives was analyzed using the cell growth inhibition assay and the cell membrane damage test. (3aR,5R,6R,7aS)-5-Azido-2-benzyl-6-hydroxyhexahydro-1H-isoindole-1,3(2H)-dione (1d), (3aR,5R,6R,7aS)-5-azido-6-((tert-butyldiphenylsilyl)oxy)-2-ethylhexahydro-1H-isoindole-1,3(2H)-dione (2a), and (3aR,5R,6R,7aS)-5-azido-6-((tert-butyldiphenylsilyl)oxy)-2-methylhexahydro-1H-isoindole-1,3(2H)-dione (2b) compounds inhibited the growth of the A549 and HeLa cells caused membrane damage and exhibited a dose-dependent cytotoxic effect on lung and cervical carcinoma cells. The effect of tert-butyldiphenylsilyl (TBDPS) groups on cytotoxicity was observed in compounds 2a and 2b, but not in the other compounds. Considering the effect of groups attached to the nitrogen atom, the best activity was exhibited in 2b molecule to which the methyl group is attached. Additionally, the interactions of compounds (3aR,5R,6R,7aS)-5-azido-6-hydroxy-2-methylhexahydro-1H-isoindole-1,3(2H)-dione (1b), 1d, 2a and 2b with mammalian rapamycin target, human ribosomal S6 kinase 1 and human epidermal growth factor receptor were investigated by molecular docking studies, . According to the docking results, 2a and 2b compounds containing a TBDPS group have stronger binding energies than 1b and 1d compounds against all target receptors. GRAPHICAL ABSTRACT
{"title":"Investigation of cytotoxic properties of some isoindole-related compounds bearing silyl and azide groups with in vitro and in silico studies","authors":"A. Tan, Aytekin Köse, D. Mete, Gülşah Şanlı‐Mohamed, Nurhan Kishali, Yunus Kara","doi":"10.1080/10426507.2023.2232509","DOIUrl":"https://doi.org/10.1080/10426507.2023.2232509","url":null,"abstract":"Abstract This study aims to evaluate the synthesis of isoindole-1,3-dione analogues and their cytotoxic potential. A549 and HeLa cells exposed to 250–100–50–25 µM doses of each derivative were incubated for 24, 48, and 72 h. The cytotoxicity of the isoindole-1,3-dione derivatives was analyzed using the cell growth inhibition assay and the cell membrane damage test. (3aR,5R,6R,7aS)-5-Azido-2-benzyl-6-hydroxyhexahydro-1H-isoindole-1,3(2H)-dione (1d), (3aR,5R,6R,7aS)-5-azido-6-((tert-butyldiphenylsilyl)oxy)-2-ethylhexahydro-1H-isoindole-1,3(2H)-dione (2a), and (3aR,5R,6R,7aS)-5-azido-6-((tert-butyldiphenylsilyl)oxy)-2-methylhexahydro-1H-isoindole-1,3(2H)-dione (2b) compounds inhibited the growth of the A549 and HeLa cells caused membrane damage and exhibited a dose-dependent cytotoxic effect on lung and cervical carcinoma cells. The effect of tert-butyldiphenylsilyl (TBDPS) groups on cytotoxicity was observed in compounds 2a and 2b, but not in the other compounds. Considering the effect of groups attached to the nitrogen atom, the best activity was exhibited in 2b molecule to which the methyl group is attached. Additionally, the interactions of compounds (3aR,5R,6R,7aS)-5-azido-6-hydroxy-2-methylhexahydro-1H-isoindole-1,3(2H)-dione (1b), 1d, 2a and 2b with mammalian rapamycin target, human ribosomal S6 kinase 1 and human epidermal growth factor receptor were investigated by molecular docking studies, . According to the docking results, 2a and 2b compounds containing a TBDPS group have stronger binding energies than 1b and 1d compounds against all target receptors. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"55 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78903376","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-10DOI: 10.1080/10426507.2023.2222868
Sondes Zairi, W. Selmi, H. Elleuch, M. Faouzi Zid, F. Rezgui
Abstract A new octahedral [SnCl4L·H2O] complex (L = γ-keto allyl phosphonate) (1) was prepared and characterized by multinuclear (1H, 13C, 31P, and 119Sn) NMR spectroscopy, IR spectroscopy, and single-crystal X-ray diffraction. The NMR data show that, in solution, the complex exclusively exists in trans isomeric form. The solution structure was confirmed by 119Sn NMR spectrum, showing a single triplet corresponding to the trans isomer. The effect of distant substituent on the metal–ligand interaction was investigated and compared to closely related tin–phosphoryl complexes. The crystal structure is stabilized by strong O-H···Cl hydrogen bonds forming layers of dimers with absence of π–π interactions. The Hirshfeld surface analysis confirms the interactions involving hydrogen atoms in the complex by the higher percentage of H···H (41.1%) and Cl···H/H···Cl (40%) interactions. Graphical abstract
{"title":"Synthesis, crystal structure, spectroscopic, and Hirshfeld surface study of a new functionalized α-hydroxyphosphonate complex of tin(IV) chloride","authors":"Sondes Zairi, W. Selmi, H. Elleuch, M. Faouzi Zid, F. Rezgui","doi":"10.1080/10426507.2023.2222868","DOIUrl":"https://doi.org/10.1080/10426507.2023.2222868","url":null,"abstract":"Abstract A new octahedral [SnCl4L·H2O] complex (L = γ-keto allyl phosphonate) (1) was prepared and characterized by multinuclear (1H, 13C, 31P, and 119Sn) NMR spectroscopy, IR spectroscopy, and single-crystal X-ray diffraction. The NMR data show that, in solution, the complex exclusively exists in trans isomeric form. The solution structure was confirmed by 119Sn NMR spectrum, showing a single triplet corresponding to the trans isomer. The effect of distant substituent on the metal–ligand interaction was investigated and compared to closely related tin–phosphoryl complexes. The crystal structure is stabilized by strong O-H···Cl hydrogen bonds forming layers of dimers with absence of π–π interactions. The Hirshfeld surface analysis confirms the interactions involving hydrogen atoms in the complex by the higher percentage of H···H (41.1%) and Cl···H/H···Cl (40%) interactions. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"17 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91366090","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-06DOI: 10.1080/10426507.2023.2223746
Masoud Ghaghaei, M. Babazadeh, F. Behmagham, L. Edjlali, E. Vessally
Abstract In this work, we have compared and contrasted the stability, polarity, polarizability, frequency, band gap, charge distribution, and global reactivity of singlet (s) and triplet (t) states of the fused benzo-4-sila-1,4-dihydropyridine-4,4-diyl as the reference structure (1-s and 1-t) as well as the fused pyrrole congeners (2x-s, and 2x-t, x = NH, PH, AsH, O, S, and Se), using density-functional theory (DFT). According to frequency data, all singlet and triplet remote N-heterocyclic silylene (RNHSi) structures appear as minimum displaying a positive force constant. Every singlet silylene as ground state exhibits more stability than its corresponding triplet congener. Consistent with Hoffmannʼs findings, the fusion of one pyrrole ring with different heteroatoms stabilizes the corresponding RNHSi more than the fusion of one benzene ring. In going from 1-s to 2x-s species and substituting of NH, PH, AsH, O, S, and Se groups, higher singlet–triplet energy difference (ΔE s-t = E t – E s) and the higher band gap is found for 2NH-s and 2 O-s structures. Interestingly, the higher thermodynamic and kinetic stability of the optimized RNHSis than the synthesized Kiraʼs silylene makes them worthy of synthetic exploration. According to the distributed charge and FMO (the frontier molecular orbital) shapes, the more negative region is localized on pyridineʼs nitrogen and the less negative region is confined over pyrroleʼs nitrogen, while the positive charge is distributed on silylenic center. This phenomenon is inconsistent with the expected canonical forms for RNHSis. GRAPHICAL ABSTRACT
{"title":"Substituent influence of heteroatom on the novel remote N-heterocyclic silylenes (RNHSis) using density functional theory","authors":"Masoud Ghaghaei, M. Babazadeh, F. Behmagham, L. Edjlali, E. Vessally","doi":"10.1080/10426507.2023.2223746","DOIUrl":"https://doi.org/10.1080/10426507.2023.2223746","url":null,"abstract":"Abstract In this work, we have compared and contrasted the stability, polarity, polarizability, frequency, band gap, charge distribution, and global reactivity of singlet (s) and triplet (t) states of the fused benzo-4-sila-1,4-dihydropyridine-4,4-diyl as the reference structure (1-s and 1-t) as well as the fused pyrrole congeners (2x-s, and 2x-t, x = NH, PH, AsH, O, S, and Se), using density-functional theory (DFT). According to frequency data, all singlet and triplet remote N-heterocyclic silylene (RNHSi) structures appear as minimum displaying a positive force constant. Every singlet silylene as ground state exhibits more stability than its corresponding triplet congener. Consistent with Hoffmannʼs findings, the fusion of one pyrrole ring with different heteroatoms stabilizes the corresponding RNHSi more than the fusion of one benzene ring. In going from 1-s to 2x-s species and substituting of NH, PH, AsH, O, S, and Se groups, higher singlet–triplet energy difference (ΔE s-t = E t – E s) and the higher band gap is found for 2NH-s and 2 O-s structures. Interestingly, the higher thermodynamic and kinetic stability of the optimized RNHSis than the synthesized Kiraʼs silylene makes them worthy of synthetic exploration. According to the distributed charge and FMO (the frontier molecular orbital) shapes, the more negative region is localized on pyridineʼs nitrogen and the less negative region is confined over pyrroleʼs nitrogen, while the positive charge is distributed on silylenic center. This phenomenon is inconsistent with the expected canonical forms for RNHSis. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"38 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89346100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-05DOI: 10.1080/10426507.2023.2232508
R. Sagar, G. Thippeshappa, G. G. Kadalli, B. Dhananjaya
Abstract The purpose of the study was to assess the influence of humic substance on the transformation of phosphorus in acid soil, so an experiment was conducted in a lab setting using the same soil (Typic Rhodustalf) collected from the land where the field experiment is expected (Agricultural and Horticultural Research Station, Tarikere taluk, Karnataka India). Humic substance employed in treatment application was extracted from farm yard manure. The study proven that, in contrast to P fertilizers applied without humic substance, application of humic substance at higher doses along with P fertilizers increased the available P status, saloid-P and organic-P fraction over the course of the incubation period, particularly when rock phosphate combined with humic substance @ 60 mg kg−1. However, compared to P fertilizers without humic substance treatments, significant decrease in in Al-P, Fe-P, reductant soluble P, occluded P and Ca-P was found in Rock phosphate + humic substance @ 60 mg kg−1 with lower P fixation (35.31%) and Rock phosphate + humic substance @ 40 mg kg−1 with P fixation of 37.32%, while the absolute control treatment (60.34%) had the maximum P fixation capacity. Graphical abstract
{"title":"Phosphorus transformation in acid soil as influenced by humic substance","authors":"R. Sagar, G. Thippeshappa, G. G. Kadalli, B. Dhananjaya","doi":"10.1080/10426507.2023.2232508","DOIUrl":"https://doi.org/10.1080/10426507.2023.2232508","url":null,"abstract":"Abstract The purpose of the study was to assess the influence of humic substance on the transformation of phosphorus in acid soil, so an experiment was conducted in a lab setting using the same soil (Typic Rhodustalf) collected from the land where the field experiment is expected (Agricultural and Horticultural Research Station, Tarikere taluk, Karnataka India). Humic substance employed in treatment application was extracted from farm yard manure. The study proven that, in contrast to P fertilizers applied without humic substance, application of humic substance at higher doses along with P fertilizers increased the available P status, saloid-P and organic-P fraction over the course of the incubation period, particularly when rock phosphate combined with humic substance @ 60 mg kg−1. However, compared to P fertilizers without humic substance treatments, significant decrease in in Al-P, Fe-P, reductant soluble P, occluded P and Ca-P was found in Rock phosphate + humic substance @ 60 mg kg−1 with lower P fixation (35.31%) and Rock phosphate + humic substance @ 40 mg kg−1 with P fixation of 37.32%, while the absolute control treatment (60.34%) had the maximum P fixation capacity. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"46 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79892231","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-06-21DOI: 10.1080/10426507.2023.2225670
Shahab Marooti, N. Noroozi Pesyan, S. Behrouz
Abstract New N-heterocylic, homocyclic and aliphatic dronic acids were synthesized through an improved facile and versatile route by the reaction of various carboxylic acids with Phosphorus trichloride (PC), phosphorus acid (PA) and methanesulfonic acid under reflux and inert atmosphere. Representatively, the dronic acid derived from stearic acid as a long chained fatty acid was also synthesized. All the obtained compounds were analyzed and characterized by means of FT IR, 1H, 13C and 31P NMR spectroscopic techniques. In addition, the compound derived from stearic acid was characterized by means of FT IR and Mass spectrometry due to its insolubility in D2O and DMSO-d 6. GRAPHICAL ABSTRACT
{"title":"An improved efficient synthesis of new N-heterocylic, homocyclic and aliphatic dronic acids","authors":"Shahab Marooti, N. Noroozi Pesyan, S. Behrouz","doi":"10.1080/10426507.2023.2225670","DOIUrl":"https://doi.org/10.1080/10426507.2023.2225670","url":null,"abstract":"Abstract New N-heterocylic, homocyclic and aliphatic dronic acids were synthesized through an improved facile and versatile route by the reaction of various carboxylic acids with Phosphorus trichloride (PC), phosphorus acid (PA) and methanesulfonic acid under reflux and inert atmosphere. Representatively, the dronic acid derived from stearic acid as a long chained fatty acid was also synthesized. All the obtained compounds were analyzed and characterized by means of FT IR, 1H, 13C and 31P NMR spectroscopic techniques. In addition, the compound derived from stearic acid was characterized by means of FT IR and Mass spectrometry due to its insolubility in D2O and DMSO-d 6. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"120 6 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76290154","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-06-20DOI: 10.1080/10426507.2023.2222871
G. E. Ayom, S. Zamisa, Thishana Singh, W. V. van Zyl
Abstract Four new polymorphs (1–4) of pentaerythritol-derived ferrocenyl S-S coupled dithiophosphonates were obtained. The four polymorphs all crystallized in the monoclinic system but different space groups. Notable differences between polymorphs 3 and 4 lie in their respective unit cell parameters; a fifth polymorph 5 of the same compound crystallized in the orthorhombic system and was previously reported by us. Structural deviations between polymorphs were performed by molecular overlays and the statistical values were expressed as root mean square deviation (RMSD). The highest structural deviations were between polymorphs 1 & 4 and 2 & 4 with an RMSD of about 1.0 while polymorphs 3 & 4 had a smaller difference with an RMSD of about 0.25. The solid-state molecular organization in the five polymorphs was also studied and discussed in terms of molecular conformation, crystal packing and hydrogen-bonded networks. Polymorphs 1–5 contain a variety of intermolecular and intramolecular non-classical hydrogen bonding interactions which form hydrogen-bonded supramolecular architectures. In all polymorphs, these hydrogen bond interactions were between the hydrogen atoms of the substituted and unsubstituted ferrocenyl moiety and the adjoining sulfur atoms of the dithiophosphonate group. A DFT geometry optimization found that 2 had the lowest energy and verified the molecular overlay. The reactivity indices further proved 2 to be the most reactive. Graphical abstract
{"title":"Polymorphism in pentaerythritol-derived ferrocenyl dithiophosphonates with intramolecular S-S coupling: a structural and computational study","authors":"G. E. Ayom, S. Zamisa, Thishana Singh, W. V. van Zyl","doi":"10.1080/10426507.2023.2222871","DOIUrl":"https://doi.org/10.1080/10426507.2023.2222871","url":null,"abstract":"Abstract Four new polymorphs (1–4) of pentaerythritol-derived ferrocenyl S-S coupled dithiophosphonates were obtained. The four polymorphs all crystallized in the monoclinic system but different space groups. Notable differences between polymorphs 3 and 4 lie in their respective unit cell parameters; a fifth polymorph 5 of the same compound crystallized in the orthorhombic system and was previously reported by us. Structural deviations between polymorphs were performed by molecular overlays and the statistical values were expressed as root mean square deviation (RMSD). The highest structural deviations were between polymorphs 1 & 4 and 2 & 4 with an RMSD of about 1.0 while polymorphs 3 & 4 had a smaller difference with an RMSD of about 0.25. The solid-state molecular organization in the five polymorphs was also studied and discussed in terms of molecular conformation, crystal packing and hydrogen-bonded networks. Polymorphs 1–5 contain a variety of intermolecular and intramolecular non-classical hydrogen bonding interactions which form hydrogen-bonded supramolecular architectures. In all polymorphs, these hydrogen bond interactions were between the hydrogen atoms of the substituted and unsubstituted ferrocenyl moiety and the adjoining sulfur atoms of the dithiophosphonate group. A DFT geometry optimization found that 2 had the lowest energy and verified the molecular overlay. The reactivity indices further proved 2 to be the most reactive. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"33 3","pages":"723 - 732"},"PeriodicalIF":0.0,"publicationDate":"2023-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91480743","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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