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Journal articles on the topic '2-(alkylsulfanyl)pyridine N-oxide'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Hay, Benjamin P., and Athelstan L. J. Beckwith. "Synthesis of N-(alkyloxy)pyridine-2(1H)-thiones: alkylations of the ambident nucleophile pyridine-2(1H)-thione N-oxide and attempted isomerizations of 2-(alkylthio)pyridine N-oxide." Journal of Organic Chemistry 54, no. 18 (September 1989): 4330–34. http://dx.doi.org/10.1021/jo00279a020.

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2

Jebas, Samuel Robinson, Balasingh Ravindran Durai Nayagam, and Thailampillai Balasubramanian. "Hexaaquamanganese(II) bis[2-(carboxylatomethylsulfanyl)pyridine N-oxide]." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (April 21, 2006): m1069—m1070. http://dx.doi.org/10.1107/s1600536806013237.

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In the title compound, [Mn(H2O)6](C7H6NO3S)2, the pyridylsulfanyl N-oxide acetate anions have no direct coordination to the MnII atom. The MnII atom is octahedrally coordinated by six water molecules and is located on an inversion centre. The cations and anions are linked by O—H...O hydrogen bonds into a three-dimensional network.

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3

Shukla, Onkar P., and Shanti M. Kaul. "Microbiological transformation of pyridine N-oxide and pyridine by Nocardia sp." Canadian Journal of Microbiology 32, no. 4 (April 1, 1986): 330–41. http://dx.doi.org/10.1139/m86-065.

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A Nocardia sp., which utilises pyridine N-oxide (PNO), 2-hydroxypyridine, and pyridine as sole sources of carbon, nitrogen, and energy, has been isolated from soil by enrichment on PNO. PNO-adapted cells rapidly oxidized PNO and 2-hydroxypyridine; pyridine was oxidized very slowly. 2-Hydroxy pyridine- and pyridine-adapted cells oxidized their respective substrates, but PNO was not oxidized. Dihydroxypyridines did not accumulate during growth of the organism, but the formation of blue pigments during fermentation of PNO and 2-hydroxypyridine suggested their transient participation. The pigment has been characterized as 4,5,4′,5′-tetrahydroxy-3,3′-diazadiphenoquinone-(2,2′). No pigment was formed during pyridine metabolism. 2,5-Dihydroxypyridine was oxidized by PNO- and 2-hydroxypyridine-adapted but not by pyridine-adapted cells. Succinic semialdehyde was characterized as the intermediate of pyridine metabolism from semicarbazide-inhibited cultures; it was rapidly oxidized by pyridine-adapted cells. Pyridine N-oxide is therefore metabolized in this Nocardia sp. via 2-hydroxypyridine and 2,5-dihydroxypyridine, but these compounds do not serve as intermediates of pyridine metabolism.

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4

Li, Shu An, Run Lai Li, Zhen Ming Zhang, Kai Zhu, and Guang Jie Wang. "Improved Preparation of 2,2-Dithiobis(Pyridine-N-Oxide)." Advanced Materials Research 554-556 (July 2012): 868–73. http://dx.doi.org/10.4028/www.scientific.net/amr.554-556.868.

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2,2-Dithiobis(pyridine-N-oxide) (1) was prepared by reacting 2-pyridinethiol-N-oxide (2) and hydrogen peroxide-urea adduct (3) at the molar ratio of 1:1.25 and 45oC for 1.75h in high yield and purity of 91.6% and 99.6% respectively. The structures of product were characterized by IR, NMR.

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5

Hiller, W., A. Castiñeiras, M. E. García- Fernandez, M. R. Bermejo, J. Bravo, and A. Sanchez. "The Crystal Structure of TlBrI2(4-methylpyridine-N-oxide)2." Zeitschrift für Naturforschung B 43, no. 1 (January 1, 1988): 132–33. http://dx.doi.org/10.1515/znb-1988-0123.

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Abstract The unit cell of TlBrI2 (4-methylpyridine-N-oxide) 2 is orthorhombic, space group Pnna. with a = 1126.9(3),b = 919.8(2),c = 1210.4(3) pm.and Z = 4. The structure consists of discrete TlBrI2 (4-methyl-pyridine-N-oxide)2 molecules which have a distorted trigonal-bipyramidal geometry. The thallium atom is coordinated to two iodine atoms and a bromine atom in equatorial positions, and by two 4-methyl-pyridine-N-oxide ligands in the axial positions.

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6

Prezhdo, V. V., E. V. Vaschenko, O. V. Prezhdo, and A. Puszko. "Molecular structure and electric properties of some pyridine and pyridine-N-oxide derivatives." Journal of Molecular Structure 471, no. 1-3 (November 1998): 127–37. http://dx.doi.org/10.1016/s0022-2860(98)00396-2.

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7

Heineking, N., H. Dreizler, K. Endo, and Y. Kamura. "High Resolution Microwave Spectra of Pyridine-N-oxideanda-Picoline-N-oxide." Zeitschrift für Naturforschung A 44, no. 12 (December 1, 1989): 1196–200. http://dx.doi.org/10.1515/zna-1989-1212.

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Abstract The rotational spectra of pyridine-N-oxide and x-picoline-N-oxide ( = 2-methvlpyridine-N-oxide) have been observed by means of pulsed microwave spectroscopy. For both molecules, the 14N quadrupole coupling constants have been obtained. For α-picoline-N-oxide. in addition the parameters of the internal rotation motion and the centrifugal distortion constants have been determined.

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8

Arvanitis, Georgia M., Michael E. Berardini, Darryl Allardice, and Phillip E. Dumas. "Structure of bis(2-pyridine-N-oxide) diselenide and its formation from tetraphenylantimony(V)selenopyridine-N-oxide." Journal of Chemical Crystallography 24, no. 7 (July 1994): 421–23. http://dx.doi.org/10.1007/bf01666088.

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9

Creary, Xavier, and M. E. Mehrsheikh-Mohammadi. "The pyridine n-oxide group. A potent radical stabilizing function." Tetrahedron Letters 29, no. 7 (January 1988): 749–52. http://dx.doi.org/10.1016/s0040-4039(00)80200-2.

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10

Lynch, Will, Genevieve Lynch, Kirk Sheriff, and Clifford Padgett. "Structures of substituted pyridine N-oxide with manganese(II) acetate." Acta Crystallographica Section E Crystallographic Communications 74, no. 10 (September 11, 2018): 1405–10. http://dx.doi.org/10.1107/s205698901801232x.

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Manganese(II) acetate coordination polymers have been prepared with three derivatives of pyridine N-oxide. The compounds are catena-poly[manganese(II)-μ3-acetato-di-μ2-acetato-[aquamanganese(II)]-μ2-acetato-μ-(pyridine N-oxide)-manganese(II)-μ3-acetato-μ2-acetato-μ-(pyridine N-oxide)-[aquamanganese(II)]-di-μ2-acetato], [Mn4(CH3COO)8(C5H5NO)2(H2O)2] n , (I), catena-poly[[manganese(II)]-μ3-acetato-μ2-acetato-μ-(2-methylpyridine N-oxide)-[aquamanganese(II)]-di-μ2-acetato-manganese(II)-di-μ2-acetato-μ3-acetato-[aquamanganese(II)]-μ2-acetato-μ-(2-methylpyridine N-oxide)], [Mn4(CH3COO)8(C6H7NO)2(H2O)2] n , (II), and catena-poly[[manganese(II)-di-μ2-acetato-μ-(4-methylpyridine N-oxide)] monohydrate], {[Mn(CH3COO)2(C6H7NO)]·H2O} n , (III). Compounds (I) and (II) both have three unique Mn atoms; in both compounds two of them sit on a crystallographic inversion center while the third is on a general position. In compound (III), the single unique Mn atom sits on a general position. Pseudo-octahedral six-coordinate manganese(II) centers are found in all compounds. All of the compounds form chains of Mn atoms bridged by acetate ions and the oxygen atom of the N-oxide in pyridine N-oxide (PNO), 2-methylpyridine N-oxide (2MePNO), or 4-methylpyridine N-oxide (4MePNO). Compound (I) and (II) both exhibit a bound water of solvation. In (I), the water hydrogen bonds to a nearby acetate whereas in (II) the water molecule forms bridging hydrogen bonds between two neighboring acetates. In compound (III) a water molecule of solvation is found in the lattice, not bound to the metal ion but hydrogen bonding to a bridging acetate.

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11

Antolovich, Michael, Lynette J. Fitzpatrick, and David J. Phillips. "COPPER(II), NICKEL(II) AND COBALT(II) COMPLEXES WITH N,N′-BIS(2-N,N-DIMETHYLAMINOETHYL)PYRIDINE-2,6-DICARBOXAMIDE 1-OXIDE. BINUCLEATING BEHAVIOUR BY A DEPROTONATED PYRIDINE N-OXIDE LIGAND." Journal of Coordination Chemistry 50, no. 1 (June 1, 2000): 119–30. http://dx.doi.org/10.1080/00958970008054930.

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12

Vrbová, Martina, Peter Baran, Roman Boča, Hartmut Fuess, Ingrid Svoboda, Wolfgang Linert, Ulrich Schubert, and Petra Wiede. "Preparation and structure of 2-(2-benzimidazol-2-yl)pyridine N-oxide and its complexes." Polyhedron 19, no. 20-21 (October 2000): 2195–201. http://dx.doi.org/10.1016/s0277-5387(00)00553-2.

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13

Zhang, Hai-Jun, Ru-Hu Gou, Lan Yan, and Ru-Dong Yang. "Synthesis, characterization and luminescence property of N,N′-di(pyridine N-oxide-2-yl)pyridine-2,6-dicarboxamide and corresponding lanthanide (III) complexes." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 66, no. 2 (February 2007): 289–94. http://dx.doi.org/10.1016/j.saa.2006.02.054.

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14

Bratulescu, George. "2-Substituted Benzimidazole Synthesis in Dry Medium Mediated by Pyridine N-oxide." Revista de Chimie 69, no. 12 (January 15, 2019): 3569–72. http://dx.doi.org/10.37358/rc.18.12.6794.

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Substituted benzimidazoles were obtained from o-phenylenediamine and organic halides in solvent-free medium. The procedure involves pyridine N-oxide as mild oxidizing agent. The benzimidazoles were prepared without the separation of the intermediates. The absence of catalysts and good yields are important benefits of the method.

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15

Jun-Hua, Zhang, Wu Yi-Rong, Wang Zheng-Hao, Li Fu-You, and Jin Lin-Pei. "Electrochemical Properties of 4-[2-4(Dimethylamino)Phenyl] Ethenyl Pyridine N-Oxide." Acta Physico-Chimica Sinica 16, no. 04 (2000): 362–65. http://dx.doi.org/10.3866/pku.whxb20000413.

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16

Pastuch, G., and W. Szeja. "ChemInform Abstract: Simple Synthesis of 2-Thioglycosyl Derivatives of Pyridine N-Oxide." ChemInform 31, no. 18 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200018147.

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17

Halfpenny, J., and R. W. H. Small. "The 1/2 complex of mercury(II) trifluoroacetate and pyridine N-oxide." Acta Crystallographica Section C Crystal Structure Communications 47, no. 4 (April 15, 1991): 869–71. http://dx.doi.org/10.1107/s0108270190011349.

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18

Greenberg, Arthur, Alexa R. Green, and Joel F. Liebman. "Computational Study of Selected Amine and Lactam N-Oxides Including Comparisons of N-O Bond Dissociation Enthalpies with Those of Pyridine N-Oxides." Molecules 25, no. 16 (August 14, 2020): 3703. http://dx.doi.org/10.3390/molecules25163703.

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A computational study of the structures and energetics of amine N-oxides, including pyridine N-oxides, trimethylamine N-oxide, bridgehead bicyclic amine N-oxides, and lactam N-oxides, allowed comparisons with published experimental data. Most of the computations employed the B3LYP/6-31G* and M06/6-311G+(d,p) models and comparisons were also made between the results of the HF 6-31G*, B3LYP/6-31G**, B3PW91/6-31G*, B3PW91/6-31G**, and the B3PW91/6-311G+(d,p) models. The range of calculated N-O bond dissociation energies (BDE) (actually enthalpies) was about 40 kcal/mol. Of particular interest was the BDE difference between pyridine N-oxide (PNO) and trimethylamine N-oxide (TMAO). Published thermochemical and computational (HF 6-31G*) data suggest that the BDE of PNO was only about 2 kcal/mol greater than that of TMAO. The higher IR frequency for N-O stretch in PNO and its shorter N-O bond length suggest a greater difference in BDE values, predicted at 10–14 kcal/mol in the present work. Determination of the enthalpy of sublimation of TMAO, or at least the enthalpy of fusion and estimation of the enthalpy of vaporization might solve this dichotomy. The “extra” resonance stabilization in pyridine N-oxide relative to pyridine was consistent with the 10–14 kcal/mol increase in BDE, relative to TMAO, and was about half the “extra” stabilization in phenoxide, relative to phenol or benzene. Comparison of pyridine N-oxide with its acyclic model nitrone (“Dewar-Breslow model”) indicated aromaticity slightly less than that of pyridine.

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19

Lynch, Sheridan, Genevieve Lynch, Will E. Lynch, and Clifford W. Padgett. "Crystal structures of four dimeric manganese(II) bromide coordination complexes with various derivatives of pyridine N-oxide." Acta Crystallographica Section E Crystallographic Communications 75, no. 8 (July 30, 2019): 1284–90. http://dx.doi.org/10.1107/s2056989019010557.

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Four manganese(II) bromide coordination complexes have been prepared with four pyridine N-oxides, viz. pyridine N-oxide (PNO), 2-methylpyridine N-oxide (2MePNO), 3-methylpyridine N-oxide (3MePNO), and 4-methylpyridine N-oxide (4MePNO). The compounds are bis(μ-pyridine N-oxide)bis[aquadibromido(pyridine N-oxide)manganese(II)], [Mn2Br4(C5H5NO)4(H2O)2] (I), bis(μ-2-methylpyridine N-oxide)bis[diaquadibromidomanganese(II)]–2-methylpyridine N-oxide (1/2), [Mn2Br4(C6H7NO)2(H2O)4]·2C6H7NO (II), bis(μ-3-methylpyridine N-oxide)bis[aquadibromido(3-methylpyridine N-oxide)manganese(II)], [Mn2Br4(C6H7NO)4(H2O)2] (III), and bis(μ-4-methylpyridine N-oxide)bis[dibromidomethanol(4-methylpyridine N-oxide)manganese(II)], [Mn2Br4(C6H7NO)4(CH3OH)2] (IV). All the compounds have one unique MnII atom and form a dimeric complex that contains two MnII atoms related by a crystallographic inversion center. Pseudo-octahedral six-coordinate manganese(II) centers are found in all four compounds. All four compounds form dimers of Mn atoms bridged by the oxygen atom of the PNO ligand. Compounds I, II and III exhibit a bound water of solvation, whereas compound IV contains a bound methanol molecule of solvation. Compounds I, III and IV exhibit the same arrangement of molecules around each manganese atom, ligated by two bromide ions, oxygen atoms of two PNO ligands and one solvent molecule, whereas in compound II each manganese atom is ligated by two bromide ions, one O atom of a PNO ligand and two water molecules with a second PNO molecule interacting with the complex via hydrogen bonding through the bound water molecules. All of the compounds form extended hydrogen-bonding networks, and compounds I, II, and IV exhibit offset π-stacking between PNO ligands of neighboring dimers.

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20

Antolovich, Michael, David J. Phillips, and A. David Rae. "X-ray crystal structure of Cu2(medpco-2H)Cl2, (medpco = N,N′-bis(2-N,N-dimethylaminoethyl)pyridine-2,6-dicarboxamide 1-oxide. Copper(II) complexes of a deprotonated binucleating pyridine N-oxide ligand." Inorganica Chimica Acta 230, no. 1-2 (March 1995): 139–44. http://dx.doi.org/10.1016/0020-1693(94)04299-b.

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21

Ramasubramanian, R., S. Kumaresan, R. Thomas, A. David Stephen, and P. Kumaradhas. "Synthesis and crystal structure investigation of pyridine-2-(3′-mercaptopropanoic acid)-N -oxide." Crystal Research and Technology 42, no. 10 (October 2007): 1024–28. http://dx.doi.org/10.1002/crat.200710916.

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22

Alam, Maksudul M., Akira Watanabe, and Osamu Ito. "Laser Flash Photolysis of 2,2'-Dithiobls(pyridine N-oxide): Reactivity of N-Oxypyridyl-2-thio Radical." Photochemistry and Photobiology 63, no. 1 (January 1996): 53–59. http://dx.doi.org/10.1111/j.1751-1097.1996.tb02991.x.

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23

Goher, Mohamed A. S., and Franz A. Mautner. "Preparation, spectral and crystal structure study of polymeric 1:1 and dimeric 1:2 complexes of copper(II) azide with pyridine-N-oxide and 3-acetylpyridine, [Cu(Pyridine-N-oxide)(N3)2]n and [Cu(3-acetylpyridine)2(N3)2]2." Polyhedron 14, no. 13-14 (July 1995): 1751–57. http://dx.doi.org/10.1016/0277-5387(94)00486-x.

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24

Li, Gang, Suling Yang, Bingjie Lv, Qingqing Han, Xingxing Ma, Kai Sun, Zhiyong Wang, Feng Zhao, Yunhe Lv, and Hankui Wu. "Metal-free methylation of a pyridine N-oxide C–H bond by using peroxides." Organic & Biomolecular Chemistry 13, no. 46 (2015): 11184–88. http://dx.doi.org/10.1039/c5ob01900a.

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Metal-free methylation of a pyridine N-oxide C–H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO₂, and OCH₃) were all suitable substrates.

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25

de Moura, Maria de F. V., Jivaldo do R. Matos, L. P. Mercuri, and Robson F. de Farias. "Synthesis and characterization of La methanesulfonate coordination compounds with pyridine-N-oxide and 2-, 3-, and 4-picoline-N-oxide." Thermochimica Acta 411, no. 1 (February 2004): 1–6. http://dx.doi.org/10.1016/j.tca.2003.07.010.

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26

Möhrle, Hans, and Robert Nießen. "Umsetzung von N-Alkylpyridinium-Salzen mit Hydroxylamin / Reaction of N-Alkylpyridinium Salts with Hydroxylamine." Zeitschrift für Naturforschung B 55, no. 5 (May 1, 2000): 434–42. http://dx.doi.org/10.1515/znb-2000-0514.

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1-Methylpyridinium salts showed no reaction with excessive hydroxylamine, but nicotinic acid derivatives in HMPT gave the corresponding N-oxides. 3-Acetyl-1-methylpyridinium iodide generated the hydroximino-pyridine 1-oxide 13 and the isoxazoles 14, 15E, and 15Z. 2- and 4-Cyano-l-methylpyridinium iodides underwent no ring cleavage, but altered only the functional group. However, the 3-cyano compound was converted into the corresponding pyridine N-oxides with carboxamide, hydroxyamidine and carbaldoxime groups.

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27

Song, Hui-Hua, and Bao-Qing Ma. "trans-4,4′-Azopyridine N,N′-dioxide dihydrochloride." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 16, 2007): o1332—o1333. http://dx.doi.org/10.1107/s1600536807006630.

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The title compound is a salt, trans-1,1′-dihydroxy-4,4′-diazenediyldipyridinium dichloride, C10H10N4O2 2+·2C l−, in which the trans-4,4′-azopyridine N,N′-dioxide cation is located on an inversion centre with the pyridine N-oxide atoms protonated. The Cl− anions form strong hydrogen bonds to these H atoms. Weak C—H...Cl hydrogen bonds link the cations and anions into a two-dimensional sheet.

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28

Beyeh, Ngong Kodiah, Rakesh Puttreddy, and Kari Rissanen. "Aromatic N-oxide templates open inclusion and dimeric capsular assemblies with methylresorcinarene." RSC Advances 5, no. 38 (2015): 30222–26. http://dx.doi.org/10.1039/c5ra03667d.

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Multiple weak interactions are manifested in the complexation of pyridine N-oxide and quinoline N-oxide by methylresorcinarene resulting to 1 : 1 assemblies in solution, with 2 : 3 and 2 : 2 host–guest dimeric capsules respectively in the solid state.

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29

Arvanitis, Georgia M., Michael E. Berardini, Thomas B. Acton, and Philip E. Dumas. "SYNTHESIS OF TWO TETRAPHENYLANTIMONY COMPLEXES OF PYRIDINE-N-OXIDES; CRYSTAL STRUCTURE OF TETRAPHENYLANTIMONY (2-MERCAPTOPYRIDINE-N-OXIDE)." Phosphorus, Sulfur, and Silicon and the Related Elements 82, no. 1-4 (February 1993): 127–35. http://dx.doi.org/10.1080/10426509308047416.

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30

Chen, Ying, Jinkun Huang, Tsang-Lin Hwang, Maosheng J. Chen, Jason S. Tedrow, Robert P. Farrell, Matthew M. Bio, and Sheng Cui. "Highly Regioselective Halogenation of Pyridine N-Oxide: Practical Access to 2-Halo-Substituted Pyridines." Organic Letters 17, no. 12 (June 3, 2015): 2948–51. http://dx.doi.org/10.1021/acs.orglett.5b01057.

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31

Chen, Mujuan, Shujuan Han, Lasheng Jiang, Songgen Zhou, Fei Jiang, Zhikai Xu, Jidong Liang, and Suhui Zhang. "New switchable [2]pseudorotaxanes formed by pyridine N-oxide derivatives with diamide-based macrocycles." Chemical Communications 46, no. 22 (2010): 3932. http://dx.doi.org/10.1039/c003118f.

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32

Agarwal, R. K., S. K. Gupta, and S. C. Rastogi. "Infrared and thermal studies of oxozirconium(IV) complexes of 2-acetyl pyridine N-oxide." Thermochimica Acta 91 (September 1985): 365–68. http://dx.doi.org/10.1016/0040-6031(85)85231-x.

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33

Kjellberg, Marianne, Alexia Ohleier, Pierre Thuéry, Emmanuel Nicolas, Lucile Anthore-Dalion, and Thibault Cantat. "Photocatalytic deoxygenation of N–O bonds with rhenium complexes: from the reduction of nitrous oxide to pyridine N-oxides." Chemical Science 12, no. 30 (2021): 10266–72. http://dx.doi.org/10.1039/d1sc01974k.

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34

Chmurzyński, L., A. Liwo, A. Wawrzynów, and A. Tempczyk. "Theoretical and experimental studies on the UV spectra of pyridine N-oxide perchlorates." Journal of Molecular Structure 143 (March 1986): 375–78. http://dx.doi.org/10.1016/0022-2860(86)85280-2.

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35

Dunstan, Pedro Oliver. "Thermochemistry of adducts of some transition metals(II) bromides with pyridine N-oxide." Thermochimica Acta 409, no. 1 (January 2004): 19–24. http://dx.doi.org/10.1016/s0040-6031(03)00333-2.

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36

den Hertog, H. J., and M. van Ammers. "The directive influence of the N-oxide group during the nitration of derivatives of pyridine-n-oxide (III). The nitration of 2- and 3-methoxypyridine-N-oxide." Recueil des Travaux Chimiques des Pays-Bas 74, no. 9 (September 2, 2010): 1160–66. http://dx.doi.org/10.1002/recl.19550740913.

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37

Winkler, St, W. Ockels, H. Budzikiewicz, H. Korth, and G. Pulverer. "2-Hydroxy-4-methoxy-5-methyIpyridin-N-oxid, ein Al3+ bindender Metabolit von Pseudomonas cepacia [1] / 2-Hydroxy-4-methoxy-5-methyl Pyridine N-Oxide, an Al3+ Complexing Metabolite from Pseudomonas cepacia [1]." Zeitschrift für Naturforschung C 41, no. 9-10 (October 1, 1986): 807–8. http://dx.doi.org/10.1515/znc-1986-9-1001.

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38

Rodríguez Arce, Esteban, M. Florencia Mosquillo, Leticia Pérez-Díaz, Gustavo A. Echeverría, Oscar E. Piro, Alicia Merlino, E. Laura Coitiño, et al. "Aromatic amine N-oxide organometallic compounds: searching for prospective agents against infectious diseases." Dalton Transactions 44, no. 32 (2015): 14453–64. http://dx.doi.org/10.1039/c5dt00557d.

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39

Vasetska, OP. "Morphofunctional changes in cells of Tetrahymena pyriformis W infusoria under the influence of plant growth regulators — derivatives of pyridine-n-oxide." Ukrainian Journal of Modern Toxicological Aspects 90, no. 1 (May 20, 2021): 40–50. http://dx.doi.org/10.33273/2663-4570-2021-90-1-40-50.

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The aim of the Research. To identify morphological changes in Tetrahymena pyriformis W infusoria under the acute exposure to plant growth regulators (PGR) — derivatives of pyridine-N-oxide and compare them to functional disorders of cells. Materials and Methods. In the research we used the 2-methylpyridine-N-oxide, 2,6-dimethylpyridine-N-oxide and their complexes with organic acids (succinic, maleic) or metal salts (ZnCl2, ZnI 2, CoCl2, MnCl2) (a total of 15 substances), synthesized at the Institute of Bioorganic chemistry and Petrochemistry, NAS, Ukraine. Studies were performed on Tetrahymena pyriformis W infusoria in isotoxic doses — at the level of toxic concentrations — LC50, LC16 and inactive concentrations (LC0). Morphological changes in cells of infusoria were assessed visually with the use of a light microscope. Structural changes in infusoria were compared to functional changes in cells (motor activity and energy state) obtained under the same experiment. Results and Conclusions. It is demonstrated that 2-methylpyridine-N-oxide, 2,6-dimethylpyridine-N-oxide and their complexes with organic acids (succinic, maleic) or metal salts (ZnCl2, ZnI2, CoCl 2, MnCl2) cause functional and morphostructural changes in infusoria, the extent of which depends on the current concentration. Morphostructural changes in infusoria under the influence of the studied PGRs are characterized by a change of shape, growth of the contractile vacuole, vesiculation, damage to the integrity of the cytoplasmic membrane, emission of cytoplasm and structural elements of cells into the nutrient medium. Complexes of methyl derivatives of pyridine-N-oxide with metal salts in the studied concentrations reduce speed and increase energy expenditure on movement, cause changes in behavioural reactions and structure of cells to a greater extent than 2-methylpyridine-N-oxide, 2,6-dimethylpyridine-N-oxide and their complexes with organic acids. Both functional and morphological changes in infusoria are more evident under the influence of studied PGR occurring at concentrations corresponding to LC50. At lower concentrations the changes in the functional activity of infusoria were observed. Comparison of the obtained functional and morphostructural indicators of the state of infusoria shows that complexes of methyl derivatives of Pyridine-N-oxide with metal salts have more toxic effects on infusoria than complexes of methyl derivatives of pyridine-N-oxide with organic acids. Reduced motor activity and an increase in energy consumption per a unit of a path of motion, together with the morphological changes of cell structure, are the indicators of toxicity of xenobiotics for infusoria and criteria for assessing their viability. Key Words: methyl derivatives of Pyridine-N-oxide, Tetrahymena pyriformis W, morphofunctional changes.

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40

Gualo-Soberanes, N., M. C. Ortega-Alfaro, J. G. López-Cortés, R. A. Toscano, H. Rudler, and C. Álvarez-Toledano. "An expedient approach to tetrahydrofuro[3,2-b]pyridine-2(3H)-ones via activation of pyridine N-oxide by triflic anhydride." Tetrahedron Letters 51, no. 24 (June 2010): 3186–89. http://dx.doi.org/10.1016/j.tetlet.2010.04.030.

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41

den Hertog, H. J., and J. Overhoff. "Pyridine-N-oxide as an intermediate for the preparation of 2- and 4-substituted pyridines." Recueil des Travaux Chimiques des Pays-Bas 69, no. 4 (September 2, 2010): 468–73. http://dx.doi.org/10.1002/recl.19500690410.

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42

Agarwal, R. K., and H. K. Rawat. "Infrared and thermal investigations of oxozirconium(IV) complexes of 2-methyl amino pyridine N-oxide." Thermochimica Acta 90 (August 1985): 361–65. http://dx.doi.org/10.1016/0040-6031(85)87117-3.

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43

Lee, Fang-Yuan, Jiann-Jyh Huang, Yu-Ju Chen, Kuan-Jiuh Lin, Gene-Hsiang Lee, Shie-Ming Peng, Jih Ru Hwu, and Kuang-Lieh Lu. "Os(CO)2(η2-SC5H4N(O))(η2-SC5H4N): structural evidence for the transformation of pyridine-2-thione N-oxide to pyridine-2-thiolate in osmium complexes." Journal of Organometallic Chemistry 690, no. 2 (January 2005): 441–49. http://dx.doi.org/10.1016/j.jorganchem.2004.09.064.

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44

Möhrle, H., and R. Nießen. "Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 2. Mitteilung N-(Alkyl)- und N-(Aryl)-substituierte Verbindungen / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 2nd Communication N-(Alkyl) and N-(Aryl) Substituted Compounds." Zeitschrift für Naturforschung B 54, no. 4 (April 1, 1999): 532–40. http://dx.doi.org/10.1515/znb-1999-0417.

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The N -alkyl- and N -aryl-isoquinolinium salts 7, 15-17 reacted with free hydroxylamine in pyridine to give the isoquinoline-2-oxide (9) as final product. The intermediate dioximes 8 were isolated and characterized by derivatisation with acetic anhydride to the oxime ester nitrile 10. From the reaction o f 8 with trifluoroacetic anhydride/triethylam ine 3-amino-isoquinoline- 2-oxide (12) resulted after hydrolysis. Due to the electronic influence the 5-nitroisoquinolinium salts 1 -3 react faster than the 5-hydroxy derivative 20. but with the same course of conversion via dioximes to amine oxides. An optimized method for preparation of the amine oxides was developed .

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45

Slouka, Jan, and Vojtěch Bekárek. "Synthesis and cyclization of some N-oxides of 2-pyridylhydrazones of mesoxalic acid derivatives." Collection of Czechoslovak Chemical Communications 53, no. 3 (1988): 626–32. http://dx.doi.org/10.1135/cccc19880626.

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Coupling of diazotized 2-aminopyridine-1-oxide with ethyl cyanoacetylcarbamate, cyanoacetamide, malononitrile, and 2-benzimidazolylacetonitrile in an acid medium afforded N-oxides of the corresponding 2-pyridylhydrazones Ia-Id, which also exist in the N-hydroxyazine tautomeric forms IIa-IId as confirmed by IR spectroscopy. Hydrazone Ia was thermally cyclized to give 2-(pyridine-1-oxide-2-yl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile (IIIa) which was converted into the corresponding thioamide IIIb, acid IIIc, and amidoxime IIId.

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46

TANG, ZHENG-XIN, XIAO-HONG LI, RUI-ZHOU ZHANG, and XIAN-ZHOU ZHANG. "THEORETICAL STUDIES ON HEATS OF FORMATION OF PYRIDINE N-OXIDES USING DENSITY FUNCTIONAL THEORY AND COMPLETE BASIS METHOD." Journal of Theoretical and Computational Chemistry 08, no. 04 (August 2009): 541–49. http://dx.doi.org/10.1142/s0219633609004897.

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The heats of formation (HOFs) for 11 pyridine N-oxide compounds are calculated by employing the hybrid density functional theory (B3LYP, B3PW91, B3P86, PBE1PBE) methods with 6-31G** basis set and ab initio CBS-4M method. It is demonstrated that the B3PW91 method is accurate to compute the reliable HOFs for pyridine N-oxide compounds. It is also noted that the HOF is the smallest for the pyridine N-oxide which has the substituent group on the para-position, such as 4-NC–c- C 5 H 4 NO , 4- H 2 NOC – C 5 H 4 N – O , and 4- HO 2 C –c- C 5 H 4 NO . In addition, we think that the HOF of 2- HO 2 C –c- C 5 H 4 NO is much larger than that of 3- HO 2 C –c- C 5 H 4 NO and 4- HO 2 C –c- C 5 H 4 NO , which may be the result of intramolecular hydrogen bond formation and further measurements are needed to reexamine the HOFs for 2- HO 2 C –c- C 5 H 4 NO , 3- HO 2 C –c- C 5 H 4 NO , and 4- HO 2 C –c- C 5 H 4 NO .

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47

Mirzaei, Masoud, Maryam Bazargan, Pouria Ebtehaj, and Joel T. Mague. "A redetermination of the structure and Hirshfeld surface analysis of poly[diaquadi-μ-hydroxido-tetrakis(μ-nicotinato N-oxide)tricopper(II)]." Acta Crystallographica Section E Crystallographic Communications 77, no. 3 (February 26, 2021): 309–13. http://dx.doi.org/10.1107/s2056989021002000.

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The product obtained from the reaction of pyridine-2,3-dicarboxylic acid and hydrated copper(II) chloride in hot aqueous NaOH solution was determined by low temperature X-ray diffraction to be [Cu3(C6H4NO3)4(OH)2(H2O)2] n or [Cu3(μ-OH)2(μ-nicNO)4(H2O)2] n (nicNO is pyridine-3-carboxylate N-oxide), a structure obtained from room temperature data and reported previously. The present determination is improved in quality and treatment of the H atoms. A Hirshfeld surface analysis of the intermolecular interactions is presented.

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48

Knighton, Richard C., and Paul D. Beer. "Axle component separated ion-pair recognition by a neutral heteroditopic [2]rotaxane." Chem. Commun. 50, no. 13 (2014): 1540–42. http://dx.doi.org/10.1039/c3cc48905a.

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A neutral heteroditopic pyridine N-oxide axle containing [2]rotaxane, synthesised via sodium cation templation, displays cooperative recognition of alkali metal cation-halide anion ion-pairs in an unprecedented axle component separated ion-pair binding fashion.

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49

Charmant, Jonathan P. H., Neil J. Hunt, Guy C. Lloyd-Jones, and Thorsten Nowak. "Modification of the Atropisomeric N,N-Ligand 2,2'-Di(pyridin-2-yl)-1,1'-binaphthalene and Its Application to the Asymmetric Allylation of Benzaldehyde." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 865–84. http://dx.doi.org/10.1135/cccc20030865.

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The atropisomeric compound 2,2'-di(pyridin-2-yl)-1,1'-binaphthalene (1) has been chlorinated, via its bis-N-oxide 2, at the 4 and 6 pyridine ring positions so as to generate the three isomeric species: 2,2'-bis(6-chloropyridin-2-yl)- (3a), 2-(4-chloropyridin-2-yl)-2'-(6-chloropyridin-2-yl)- (3b) and 2,2'-bis(4-chloropyridin-2-yl)-1,1'-binaphthalene (3c). The dichlorinated compounds underwent Ni-catalysed Kumada cross-coupling with MeMgI to give the methylated pyridine isomers: 2,2'-bis(6-methylpyridin-2-yl)- (4a), 2-(4-methylpyridin-2-yl)-2'-(6-methylpyridin-2-yl)- (4b) and 2,2'-bis(4-methylpyridin-2-yl)-1,1'-binaphthalene (4c). The enantiomerically pure forms of the six novel ligands (3a-3c and 4a-4c), prepared from enantiomerically pure 2,2'-di(pyridin-2-yl)-1,1'-binaphthalene (1), were tested in asymmetric catalysis, but proved to be no better and in most cases poorer than parent 1. The coordination of the ligands to Zn and Pd fragments has been explored and compared with the parent compound 1 so as to rationalise the negative effect of pyridine substitution on asymmetric induction in the zinc-catalysed allylation of benzaldehyde.

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Suehiro, Takafumi, Takashi Niwa, Hideki Yorimitsu, and Koichiro Oshima. "ChemInform Abstract: Palladium-Catalyzed (N-Oxido-2-pyridinyl)methyl Transfer from 2-(2-Hydroxyalkyl)pyridine N-Oxide to Aryl Halides by Î²-Carbon Elimination." ChemInform 40, no. 51 (December 22, 2009): no. http://dx.doi.org/10.1002/chin.200951164.

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