Pyridine 1 Oxide

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Jing-jer Jwo - One of the best experts on this subject based on the ideXlab platform.

  • Inverse phase transfer catalysis: kinetics of the Pyridine-1-Oxide-catalyzed two-phase reactions of methyl-, methoxy-, iodo-, and nitro-benzoyl chlorides and benzoate ions
    Journal of Molecular Catalysis A-chemical, 2001
    Co-Authors: Jing-jer Jwo
    Abstract:

    Abstract The substitution reactions of XC 6 H 4 COCl [X=2-, 3-, or 4-CH 3 ; 2-, 3-, or 4-CH 3 O; 2-, or 4-I; or 2-, 3-, or 4-NO 2 ] and YC 6 H 4 COONa [Y=2-, 3-, or 4-CH 3 ; 2-, 3-, or 4-CH 3 O; 2-I; 4-NO 2 ; or H] in a two-phase H 2 O/CH 2 Cl 2 medium using Pyridine-1-Oxide (PNO) as an inverse phase transfer catalyst were investigated. In general, the kinetics of the reaction follows a pseudo-first-order rate law, with the observed rate constant being a linear function of the concentration of PNO in the water phase. In contrast to other analogous reactions, the hydrolysis reaction of 2-, 3-, or 4-NO 2 C 6 H 4 COCl in H 2 O/CH 2 Cl 2 medium is catalyzed considerably by PNO and reaches an equilibrium. In the PNO-catalyzed reaction of XC 6 H 4 COCl and XC 6 H 4 COONa in H 2 O/CH 2 Cl 2 medium, the order of reactivities of XC 6 H 4 COCl toward reaction with PNO in CH 2 Cl 2 is 2-IC 6 H 4 COCl>4-IC 6 H 4 COCl>(C 6 H 5 COCl,3-CH 3 OC 6 H 4 COCl)>3-CH 3 C 6 H 4 COCl>(2-CH 3 C 6 H 4 COCl,4-CH 3 C 6 H 4 COCl)>4-CH 3 OC 6 H 4 COCl>2-CH 3 OC 6 H 4 COCl. Combined with the results of other analogous reactions, good Hammett correlations with positive reaction constant were obtained for the meta - and para -substituents, which supports that the XC 6 H 4 COCl–PNO reaction in CH 2 Cl 2 is a nucleophilic substitution reaction.

  • Inverse phase transfer catalysis: kinetics of the Pyridine 1-Oxide-catalyzed two-phase reactions of fluoro- and butyl-benzoyl chlorides and benzoate ions
    Journal of Molecular Catalysis A-chemical, 2000
    Co-Authors: Shu-mei Hung, Jing-jer Jwo
    Abstract:

    Abstract The substitution reactions of XC 6 H 4 COCl (X=2-F, 3-F, 4-F, or 4-(CH 3 ) 3 C) and YC 6 H 4 COONa (Y=2-F, 3-F, 4-F, or H) in a two-phase H 2 O/CH 2 Cl 2 medium using Pyridine 1-Oxide (PNO) as an inverse phase transfer catalyst were investigated. Under suitable reaction conditions, the kinetics of the reaction follows a pseudo-first-order rate law, with a constant observed rate being a linear function of the concentration of PNO in the water phase. The order of reactivities of XC 6 H 4 COCl toward reaction with PNO is 2-FC 6 H 4 COCl>3-FC 6 H 4 COCl>4-FC 6 H 4 COCl>C 6 H 5 COCl>4-(CH 3 ) 3 CC 6 H 4 COCl. The order of reactivities of YC 6 H 4 COO − ions toward reaction with 1-(benzoyloxy)pyridinium (C 6 H 5 COONP + ) ion is C 6 H 5 COO − >3-FC 6 H 4 COO − >4-FC 6 H 4 COO − >2-FC 6 H 4 COO − . For the water phase with pH>12, the reaction is complicated by the competitive reaction of XC 6 H 4 COCl and OH − ion in the organic phase.

  • Inverse phase transfer catalysis. Kinetics of the Pyridine 1-Oxide-catalyzed reactions of dichlorobenzoyl chlorides and benzoate ions
    Journal of Molecular Catalysis A: Chemical, 2000
    Co-Authors: Yung Sheng Chang, Jing-jer Jwo
    Abstract:

    Abstract The substitution reactions of 2,3-, 2,4-, 3,4-, or 3,5-dichlorobenzoyl chloride (Cl 2 C 6 H 3 COCl) and 2,3-, 2,4-, 3,4-, or 3,5-dichlorobenzoate ion (Cl 2 C 6 H 5 COO − ) or benzoate ion (C 6 H 5 COO − ) in a two-phase H 2 O/CH 2 Cl 2 medium using Pyridine 1-Oxide (PNO) as an inverse phase transfer catalyst were investigated. The reaction of Cl 2 C 6 H 3 COCl and PNO in CH 2 Cl 2 to produce the ionic intermediate, 1-(dichlorobenzoyloxy)-pyridinium chloride (Cl 2 C 6 H 3 COONP + Cl − ) is the rate-determining step. In the PNO-catalyzed two-phase reaction of Cl 2 C 6 H 3 COCl and C 6 H 5 COONa, the order of reactivities of Cl 2 C 6 H 3 COCl toward reaction with PNO is (2,3-, 2,4-)>3,5->3,4-≫2,6-Cl 2 C 6 H 3 COCl, whereas it is 3,5->(2,3-, 3,4-)>2,4-Cl 2 C 6 H 3 COCl in the PNO-catalyzed two-phase reaction of Cl 2 C 6 H 3 COCl and the corresponding Cl 2 C 6 H 3 COONa. The order of reactivities of Cl 2 C 6 H 3 COO − ions towards the reaction with 1-(benzoyloxy)-pyridinium (C 6 H 5 COONP + ) ion is (3,4-, 3,5-)>(2,3-, 2,4-Cl 2 C 6 H 3 COO − ).

  • Study of the exchange reaction of benzoic and 2-chlorobenzoic anhydrides in chloroform. Effects of Pyridine 1-Oxide and benzoate salts
    Journal of Molecular Catalysis A-chemical, 1998
    Co-Authors: Yau-jeng Wong, Jing-jer Jwo
    Abstract:

    Abstract Benzoic anhydride ((PhCO) 2 O) and 2-chlorobenzoic anhydride ((2-ClC 6 H 4 CO) 2 O) undergo slow exchange reaction in CHCl 3 to produce mixed benzoic 2-chlorobenzoic anhydride (2-ClC 6 H 4 COOCOPh). The rate of conversion changes abnormally with the concentration ratio of [(PhCO) 2 O]/[(2-ClC 6 H 4 CO) 2 O]. The reaction is catalyzed by Pyridine 1-Oxide (PNO). When (2-ClC 6 H 4 CO) 2 O is the limiting reactant, the presence of benzoate salt promotes the reaction substantially with the order of effectiveness being PhCOOLi, PhCOONBu 4 >PhCOONa>PhCOOH. This exchange reaction does not follow simple second-order or pseudo-first-order kinetics. However, under pseudo-order reaction condition and in the presence of PNO or benzoate salt, the reaction follows pseudo-first-order kinetics. The mechanism of the reaction is more complicated than expected. Mechanistic rationalization of experimental results is presented.

  • Kinetics of the reaction of benzoyl chloride and sodium carboxylate under inverse phase-transfer catalysis
    Journal of Molecular Catalysis A: Chemical, 1995
    Co-Authors: Maw-ling Wang, Jing-jer Jwo
    Abstract:

    The reaction of benzoyl chloride and sodium carboxylate using Pyridine 1-Oxide (PNO) as an inverse phase-transfer catalyst in a system of the two phases H2O and CH2Cl2 was investigated. Carboxylate ions including formate, acetate, propionate, 2-methylpropanoate, pentanoate, hexanoate, heptanoate and octanoate were selected to compare their reactivities. The rate of reaction depended on the concentration of Pyridine 1-Oxide (PNO) in the organic phase. The concentration of carboxylate ion affected the distribution of Pyridine 1-Oxide (PNO) between the organic and aqueous phases. The rate of reaction thus depended on the concentration of the carboxylate ion even though the rate-determining step occurred in the organic phase.

Li-zhuang Chen - One of the best experts on this subject based on the ideXlab platform.

  • Self-assembly of 1-D and 3-D transition-metal coordination polymers based on 4-(1H-l,3-benzimidazol-2-yl)Pyridine 1-Oxide
    Journal of Coordination Chemistry, 2015
    Co-Authors: Li-zhuang Chen, Qi-jian Pan, Deng-deng Huang, Cao Xingxing
    Abstract:

    Three metal-organic coordination polymers based on 4-(1H-l,3-benzimidazol-2-yl)Pyridine 1-Oxide (BImPyO) with the molecular structures [Cu2(C12H8N3O)2]n (1), [Cu(C12H8N3O)]n (2), and [Zn(C12H8N3O)Cl]n (3) were synthesized under hydrothermal conditions. They showed diverse coordination modes and were further characterized by elemental analysis, infrared spectroscopy, and single crystal X-ray structure analysis, respectively. In 1 and 2, BImPyO generated a 1-D chain by adopting μ2-kN : kN′ coordination to bridge two Cu(II) ions with bis-N-chelation. In 3, by adopting μ3-kN : kN′:kO coordination, BImPyO bridged three crystallographically independent Zn(II) ions to form a 3-D framework; 3 exhibits strong fluorescent emission in the solid state at room temperature.

  • Self-assembly of 1-D, 2-D, and 3-D transition-metal coordination polymers based on a T-shaped tripodal ligand 4-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine 1-Oxide
    Journal of Coordination Chemistry, 2015
    Co-Authors: Li-zhuang Chen, Qi-jian Pan, Deng-deng Huang, Cao Xingxing
    Abstract:

    Three coordination polymers, {[Co(C10H5N3O5)(H2O)2]·H2O}n (1), {[Mn3(C10H5N3O5)2Cl2(H2O)6]·2H2O}n (2), and {[Cu3(C10H4N3O5)2(H2O)3]·4H2O}n (3), based on a T-shaped tripodal ligand 4-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine 1-Oxide (H3DCImPyO), were synthesized under hydrothermal conditions. The polymers showed diverse coordination modes, being characterized by elemental analysis, infrared spectroscopy, and single-crystal X-ray structure analysis. In 1, the HDCImPyO2− generated a 1-D chain by adopting a μ2-kN, O : kN′, O′ coordination mode to bridge two Co(II) ions in two bis-N,O-chelating modes. In 2, the HDCImPyO2− adopted a μ3-kN, O : kO′, O′′ : O′′′ coordination mode to bridge two crystallographically independent Mn(II) ions, forming a 2-D hcb network with {63} topology. In 3, by adopting μ4-kN, O : kO′, O′′ : kN′′, O′′′ : O′′′′ coordination, DCImPyO3− bridged three crystallographically independent Cu(II) ions to form a 3-D framework having the stb topology.

  • Construction of three metal-organic frameworks based on multifunctional T-shaped tripodal ligands (4,5-dicarboxy-1H-imidazol-2-yl)Pyridine-1-Oxide
    Journal of Coordination Chemistry, 2012
    Co-Authors: Li-zhuang Chen, Fang-ming Wang, Hong Shu
    Abstract:

    Three metal-organic frameworks, [Eu(C10H6N3O5)3(H2O)2] · H2O (1), [Tb(C10H6N3O5)3(H2O)2] · H2O (2), and [Cd(C10H6N3O5)2Cl2] (3) based on T-shaped tripodal ligands 3-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine-1-Oxide and 4-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine-1-Oxide (H3DCImPyO), have been synthesized by the hydrothermal method and characterized by elemental analysis, IR, and single-crystal X-ray structure analysis. The diverse coordination modes of H3DCImPyO ligands have afforded the three compounds. Complexes 1 and 2 are isomers and the Ln (Ln = Eu or Tb) atoms have coordination number eight with a distorted square prism geometry. The partly deprotonated H2DCImPyO− ligands display three different coordination modes to link Ln (Ln = Tb or Eu) into 1-D double chains. In 3, Cd(II) lies on an inversion center and displays a slightly distorted octahedral coordination. All three compounds exhibit strong fluorescent emissions in the solid state at room temperature.

Cao Xingxing - One of the best experts on this subject based on the ideXlab platform.

  • Self-assembly of 1-D and 3-D transition-metal coordination polymers based on 4-(1H-l,3-benzimidazol-2-yl)Pyridine 1-Oxide
    Journal of Coordination Chemistry, 2015
    Co-Authors: Li-zhuang Chen, Qi-jian Pan, Deng-deng Huang, Cao Xingxing
    Abstract:

    Three metal-organic coordination polymers based on 4-(1H-l,3-benzimidazol-2-yl)Pyridine 1-Oxide (BImPyO) with the molecular structures [Cu2(C12H8N3O)2]n (1), [Cu(C12H8N3O)]n (2), and [Zn(C12H8N3O)Cl]n (3) were synthesized under hydrothermal conditions. They showed diverse coordination modes and were further characterized by elemental analysis, infrared spectroscopy, and single crystal X-ray structure analysis, respectively. In 1 and 2, BImPyO generated a 1-D chain by adopting μ2-kN : kN′ coordination to bridge two Cu(II) ions with bis-N-chelation. In 3, by adopting μ3-kN : kN′:kO coordination, BImPyO bridged three crystallographically independent Zn(II) ions to form a 3-D framework; 3 exhibits strong fluorescent emission in the solid state at room temperature.

  • Self-assembly of 1-D, 2-D, and 3-D transition-metal coordination polymers based on a T-shaped tripodal ligand 4-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine 1-Oxide
    Journal of Coordination Chemistry, 2015
    Co-Authors: Li-zhuang Chen, Qi-jian Pan, Deng-deng Huang, Cao Xingxing
    Abstract:

    Three coordination polymers, {[Co(C10H5N3O5)(H2O)2]·H2O}n (1), {[Mn3(C10H5N3O5)2Cl2(H2O)6]·2H2O}n (2), and {[Cu3(C10H4N3O5)2(H2O)3]·4H2O}n (3), based on a T-shaped tripodal ligand 4-(4,5-dicarboxy-1H-imidazol-2-yl)Pyridine 1-Oxide (H3DCImPyO), were synthesized under hydrothermal conditions. The polymers showed diverse coordination modes, being characterized by elemental analysis, infrared spectroscopy, and single-crystal X-ray structure analysis. In 1, the HDCImPyO2− generated a 1-D chain by adopting a μ2-kN, O : kN′, O′ coordination mode to bridge two Co(II) ions in two bis-N,O-chelating modes. In 2, the HDCImPyO2− adopted a μ3-kN, O : kO′, O′′ : O′′′ coordination mode to bridge two crystallographically independent Mn(II) ions, forming a 2-D hcb network with {63} topology. In 3, by adopting μ4-kN, O : kO′, O′′ : kN′′, O′′′ : O′′′′ coordination, DCImPyO3− bridged three crystallographically independent Cu(II) ions to form a 3-D framework having the stb topology.

Benjamin P. Hay - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and selected lanthanide coordination chemistry of new ((1H-pyrazol-1-yl)methyl)Pyridine and -Pyridine 1-Oxide ligands
    Polyhedron, 2015
    Co-Authors: Sabrina Ouizem, Daniel Rosario-amorin, Diane A. Dickie, Benjamin P. Hay, Robert T. Paine
    Abstract:

    Abstract Syntheses for new potentially chelating ligands, 2,6-bis((1H-pyrazol-1-yl)methyl)Pyridine 1-Oxide (2), ((6-((1H-pyrazol-1-yl)methyl)pyridin-2-yl)methyl)diphenylphosphine Oxide (4) and 2-((1H-pyrazol-1-yl)methyl)-6-((diphenylphosphoryl)methyl)Pyridine 1-Oxide (5), that are based upon Pyridine or Pyridine N-Oxide platforms functionalized with pyrazol-1-ylmethyl and diphenylphosphinoylmethyl substituents, are reported along with results from molecular modeling analyses that assess the strain energy encountered by the ligands in tridentate chelate interactions for gas phase [Eu(L)3+]complexes. Coordination chemistry with selected lanthanide nitrates is described along with X-ray crystal structure determinations for the three ligands and three representative coordination complexes.

  • Synthesis and f-element ligation properties of NCMPO-decorated Pyridine N-Oxide platforms
    Dalton transactions (Cambridge England : 2003), 2014
    Co-Authors: Sabrina Ouizem, Daniel Rosario-amorin, Diane A. Dickie, Benjamin P. Hay, Robert T. Paine, A. De Bettencourt-dias, Julien Podair, Lætitia H. Delmau
    Abstract:

    Stepwise syntheses of 2-{[2-(diphenylphosphoryl)acetamido]methyl}Pyridine 1-Oxide, 2-[Ph2P(O)CH2C(O)N(H)CH2]C5H4NO (6), 2-{[2-(diphenylphosphoryl)acetamido]methyl}-6-[(diphenylphosphoryl)methyl]Pyridine 1-Oxide, 2-[Ph2P(O)CH2C(O)N(H)CH2]-6-[Ph2P(O)CH2]C5H3NO (7) and 2,6-bis{[2-(diphenylphosphoryl)acetamido]methyl}Pyridine 1-Oxide, 2,6-[Ph2P(O)CH2C(O)N(H)CH2]2C5H3NO (8), are reported along with spectroscopic characterization data and single crystal X-ray diffraction structure determination for 6·2H2O, 7 and 2,6-[Ph2P(O)CH2C(O)N(H)CH2]2C5H3N·MeOH 18·MeOH, the Pyridine precursor of 8. Molecular mechanics computations indicate that 6, 7 and 8 should experience minimal steric hindrance to donor group reorganization that would permit tridentate, tetradentate and pentadentate docking structures for the respective ligands on lanthanide cations. However, crystal structure determination for the lanthanide complexes, {[Yb(6)(NO3)3]·(MeOH)}n, {[Lu(6)(NO3)3]·(MeOH)}n, [Er(6)2(H2O)2](NO3)3·(H2O)4}n, {[La(13)(NO3)3(MeOH)]·(MeOH)}n, {[Eu(7)(NO3)2(EtOAc)0.5(H2O)0.5](NO3)}2·MeOH and [Dy3(7)4(NO3)4(H2O)2](NO3)5·(MeOH)5·(H2O)2 reveal solid-state structures with mixed chelating/bridging ligand : Ln(III) interactions that employ lower than the maximal denticity. The binding of 6 and 7 with Eu(III) in the solid state and in MeOH solutions is also accessed by emission spectroscopy. The acid dependence for solvent extractions with 6 and 7 in 1,2-dichloroethane for Eu(III) and Am(III) in nitric acid solutions is described and compared with the behavior of n-octyl(phenyl)-N,N-diisobutylcarbamoylmethylphosphine Oxide (OPhDiBCMPO, 1b) and 2-[(diphenyl)phosphinoylmethyl]Pyridine N-Oxide (DPhNOPO, 4a).

  • Synthesis and Selected Reactivity Studies of a Dissymmetric (PhosphinoylmethylPyridine N-Oxide) Methylamine Platform
    European Journal of Organic Chemistry, 2014
    Co-Authors: Sabrina Ouizem, Diane A. Dickie, Robert T. Paine, Sylvie Pailloux, Alisha D. Ray, Eileen N. Duesler, Benjamin P. Hay
    Abstract:

    Efficient syntheses for the precursor molecules, 2-{6-[((diphenylphosphoryl)methyl)pyridin-2-yl]methyl}isoindoline-1,3-dione (2), 2-[(1,3-dioxoisoindolin-2-yl)methyl]-6-[(diphenylphosphoryl)methyl]Pyridine 1-Oxide (3), and their 6-[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl analogues are reported along with their transformations into the dissymmetric ligands, [(6-(aminomethyl)pyridin-2-yl)methyl]diphenylphosphine Oxide (4), 2-(aminomethyl)-6-[(diphenylphosphoryl)methyl]Pyridine 1-Oxide (5) and 2-(aminomethyl)-6-{[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl}Pyridine 1-Oxide (5-F). Selected reactivity of the aminomethyl substituent of 4 and 5, as well as complexation reactions of several of the compounds with lanthanide(III) ions are described. Molecular structures of three uniquely different complexes, {Pr{2-[HC(O)N(H)CH2]-6-[Ph2P(O)CH2]C5H3NO}(NO3)3(MeOH)}2, {Eu{2-[(Me2N)2CN(H+)CH2]-6-[Ph2P(O)CH2]C5H3N(H)+}(NO3)4(OMe)} and {Er{2-[(C8H4O2)NCH2]-6-[Ph2P(O)CH2]C5H3N(O)}(NO3)3(MeOH)}·(CH3)2CO, have been determined by single-crystal X-ray diffraction methods. The observed and computationally modeled structures that employ bidentate and tridentate ligand/metal interactions are compared. These results suggest further ligand modifications that should provide improved solvent extraction reagents.

  • Synthesis and coordination properties of trifluoromethyl decorated derivatives of 2,6-bis[(diphenylphosphinoyl)methyl]Pyridine N-Oxide ligands with lanthanide ions.
    Inorganic chemistry, 2009
    Co-Authors: Sylvie Pailloux, Robert T. Paine, Alisha D. Ray, Eileen N. Duesler, Cornel Edicome Shirima, John R. Klaehn, Michael E. Mcilwain, Benjamin P. Hay
    Abstract:

    Phosphinoyl Grignard-based substitutions on 2,6-bis(chloromethyl)Pyridine followed by N-oxidation of the intermediate 2,6-bis(phosphinoyl)methylPyridine compounds with mCPBA give the target trifunctional ligands 2,6-bis[bis(2-trifluoromethylphenyl)phosphinoylmethyl]Pyridine 1-Oxide (2a) and 2,6-bis[bis(3,5-bis(trifluoromethyl)phenyl)phosphinoylmethyl]Pyridine 1-Oxide (2b) in high yields. The ligands have been spectroscopically characterized, the molecular structures confirmed by single crystal X-ray diffraction methods, and the coordination chemistry surveyed with lanthanide nitrates. Single crystal X-ray diffraction analyses are described for the coordination complexes Nd(2a)(NO3)3, Nd(2a)(NO3)3·(CH3CN)0.5, Eu(2a)(NO3)3, and Nd(2b)(NO3)3·(H2O)1.25; in each case the ligand binds in a tridentate mode to the Ln(III) cation. These structures are compared with the structures found for lanthanide coordination complexes of the parent NOPOPO ligand, [Ph2P(O)CH2]2C5H3NO.

Suresh Reddy Cirandur - One of the best experts on this subject based on the ideXlab platform.

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