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1

Shirvan, Sadif A., та Sara Haydari Dezfuli. "Bis(acetato-κO)bis(2-pyridinealdoxime-κ2N,N′)cadmium". Acta Crystallographica Section E Structure Reports Online 68, № 8 (2012): m1080—m1081. http://dx.doi.org/10.1107/s1600536812031819.

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In the title molecule, [Cd(CH3COO)2(C6H6N2O)2], the CdIIcation isN,N′-chelated by two 2-pyridinealdoxime ligands and coordinated by two acetate anions in a distorted octahedral geometry. The hydroxy groups of the 2-pyridinealdoxime ligands link to the acetate anionsviaintramolecular O—H...O hydrogen bonds. Weak intermolecular C—H...O hydrogen bonds occur in the crystal.
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2

Kumagai, Hitoshi, Satoshi Kawata та Yoshiyuki Sakamoto. "catena-Poly[[[bis(4-pyridinealdoxime-κN1)zinc]-μ-benzene-1,4-dicarboxylato-κ2O1:O4] 4-pyridinealdoxime monosolvate]". Acta Crystallographica Section E Structure Reports Online 69, № 4 (2013): m216. http://dx.doi.org/10.1107/s1600536813006107.

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3

Mashaly, M. M., and M. Hammoudab. "New Simple and One-Pot Synthetic Routes to Polyfunctionally Substituted Pyridines; 1,4-Dihydropyridazines and 4H-1,2-Oxazine." Zeitschrift für Naturforschung B 54, no. 9 (1999): 1205–9. http://dx.doi.org/10.1515/znb-1999-0919.

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Reactions of arylidenemalononitriles la-d with 2-cyano-1,1-diaminoethene (5); arylhydrazones 14a,b and syn-2-pyridinealdoxime 15 afforded the title derivatives 3a-d; 16a,b and 17, respectively. Bipyridyl derivatives 11-13 were also synthesized. Unambiguous syntheses and/ or spectral analyses confirmed the suggested structures of 3a-d, 11-13, 16a,b and 17.
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4

Lee, Tae Yang, Eun Mi Son, Burm-Jong Lee, Eun Mi Park, Chungkyun Kim, and Young-Soo Kwon. "Monolayer Properties of a 4-Pyridinealdoxime-Containing Carbosilane Dendrimer." Molecular Crystals and Liquid Crystals 377, no. 1 (2002): 161–64. http://dx.doi.org/10.1080/713738507.

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5

Konidaris, Konstantis F., Christina D. Polyzou, George E. Kostakis, et al. "Metal ion-assisted transformations of 2-pyridinealdoxime and hexafluorophosphate." Dalton Trans. 41, no. 10 (2012): 2862–65. http://dx.doi.org/10.1039/c1dt11881a.

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6

Ketchersid, Mary L., Frederick W. Plapp, and Morris G. Merkle. "Sorghum (Sorghum bicolor) Seed Safeners as Insecticide Synergists." Weed Science 33, no. 6 (1985): 774–78. http://dx.doi.org/10.1017/s0043174500083338.

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Certain oximes, including cyometrinil [(Z)-α-(cyanomethoxy)iminobenzeneacetonitrile], CGA-92194 [N-(1,3-dioxolan-2-yl-methoxy)-iminobenzeneacetonitrile], 2-pyridinealdoxime-O-benzyl ether (PA-B), and 2-pyridinealdoxime-O-phenethyl ether (PA-PE), which are known to protect sorghum from chloroacetanilide herbicides, increased the toxicity of the insecticide propoxur (o-isopropoxyphenyl-methyl carbamate) to a resistant strain of housefly (Musca domesticaL.). Flurazole [5-thiazolecarboxylic acid, benzyl ester, 2-chloro-4-(trifluoromethyl)], a nonoxime protectant for grain sorghum, had less effect
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7

Konidaris, Konstantis F., Vlasoula Bekiari, Eugenia Katsoulakou, et al. "Investigation of the zinc(ii)–benzoate–2-pyridinealdoxime reaction system." Dalton Transactions 41, no. 13 (2012): 3797. http://dx.doi.org/10.1039/c2dt11853j.

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8

Kozaka, Kengo, Junji Noro, Yujiro Watanabe, and Yu Komatsu. "Solvent Extraction of Nickel(II) Using Ionic Liquid Containing 2-Pyridinealdoxime." BUNSEKI KAGAKU 57, no. 8 (2008): 593–97. http://dx.doi.org/10.2116/bunsekikagaku.57.593.

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9

Fujinaga, Kaoru, Kengo Kozaka, Yujiro Watanabe, Yu Komatsu, and Junji Noro. "Solvent Extraction of Divalent Metal Ions Using 2-Pyridinealdoxime in Ionic Liquid." Journal of Ion Exchange 18, no. 4 (2007): 374–77. http://dx.doi.org/10.5182/jaie.18.374.

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10

Okazaki, S., H. Nakagawa, K. Fukuda, et al. "Re-activation of an amperometric organophosphate pesticide biosensor by 2-pyridinealdoxime methochloride." Sensors and Actuators B: Chemical 66, no. 1-3 (2000): 131–34. http://dx.doi.org/10.1016/s0925-4005(00)00322-1.

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11

Roubeau, Olivier, Lollita Lecren, Yang-Guang Li, Xavier F. Le Goff, and Rodolphe Clérac. "Hexa- and nonanuclear manganese clusters based on the chelating ligand 2-pyridinealdoxime." Inorganic Chemistry Communications 8, no. 3 (2005): 314–18. http://dx.doi.org/10.1016/j.inoche.2005.01.008.

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12

Bucci, R., V. Carunchio, A. D. Magrí, and A. L. Magrì. "Spectral and thermal studies of copper(II) complexes of 3- and 4-pyridinealdoxime." Journal of Thermal Analysis 30, no. 6 (1985): 1309–15. http://dx.doi.org/10.1007/bf01914300.

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13

Flakus, Henryk T., and Anna Michta. "Strong coupling effects in the polarized IR spectra of the chain hydrogen bond systems in 3-pyridinealdoxime and 4-pyridinealdoxime crystals: H/D isotopic self-organization effects in the IR spectra." Journal of Molecular Structure 741, no. 1-3 (2005): 19–29. http://dx.doi.org/10.1016/j.molstruc.2005.01.043.

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14

Azzouz, A. S., K. A. Abdullah, and Kh I. Niemi. "Some observations on kinetic and stability constants of 2-pyridinealdoxime with some positive ions." Microchemical Journal 43, no. 1 (1991): 54–57. http://dx.doi.org/10.1016/0026-265x(91)90037-p.

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15

Zhang, Suyun, Lina Zhen, Bin Xu, et al. "Wheel-like MnII6 and NiII6 complexes from the use of 2-pyridinealdoxime and carboxylates." Dalton Transactions 39, no. 15 (2010): 3563. http://dx.doi.org/10.1039/b922672a.

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16

Jung, Sang-Burm, Seung-Yeop Yoo, Eunmi Park, Chungkyun Kim, and Young-Soo Kwon. "Effect of Complex on Electrical Properties of Dendrimer Langmuir–Blodgett Films Containing 48 Pyridinealdoxime." Japanese Journal of Applied Physics 41, Part 1, No. 5A (2002): 3065–68. http://dx.doi.org/10.1143/jjap.41.3065.

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17

S., C. Nayak, K. Das P., and K. Sahoo K. "Mixed ligand complexes of manganese, cobalt and zinc with 2-pyridinealdoxime and some neutral ligands." Journal of Indian Chemical Society Vol. 80, Jan 2003 (2003): 49–50. https://doi.org/10.5281/zenodo.5835766.

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Department of Chemistry, B. N. M.A. College, Paliabindha, Bhadrak-756 167, India <em>E-mail :</em> saratnayak I @rediffmail.com Department of Chemsitry, F. M. College, Balasore-756 001, India P. G. Department of Chemistry, Bhadrak College, Bhadrak-756 100, India <em>Manuscript&nbsp;received 13 November 200/. revised 6 August 2002. accepted 6 September 2002</em> Complexes of the type [ML<sub>2</sub>B<sub>2</sub>], where M = Mn<sup>II</sup> , Co<sup>II</sup>, L = 2-pyridinealdoxime, B = neutral ligands (benzimidazole, bcnzotriazolc, triazole, carbazole) and [MLB<sub>2</sub>]CI, where M = Zn<sup>
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18

Konidaris, Konstantis F., Catherine P. Raptopoulou, Vassilis Psycharis, Spyros P. Perlepes, Evy Manessi-Zoupa, and Theocharis C. Stamatatos. "Use of the 2-Pyridinealdoxime/N,N′-Donor Ligand Combination in Cobalt(III) Chemistry: Synthesis and Characterization of Two Cationic Mononuclear Cobalt(III) Complexes." Bioinorganic Chemistry and Applications 2010 (2010): 1–7. http://dx.doi.org/10.1155/2010/159656.

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The use of 2-pyridinealdoxime (paoH)/N,N′-donor ligand (L-L) “blend” in cobalt chemistry has afforded two cationic mononuclear cobalt(III) complexes of the general type [Co(pao)2(L-L)]+, where L-L = 1,10-phenanthroline (phen) and 2,2′-bipyridine (bpy). The CoCl2/paoH/L-L (1 : 2 : 1) reaction system in MeOH gives complexes [CoIII(pao)2(phen)]Cl⋅2H2O (1⋅2H2O) and [CoIII(pao)2(bpy)]Cl⋅1.5MeOH (2⋅1.5MeOH). The structures of the complexes were determined by single-crystal X-ray crystallography. The CoIIIions are six-coordinate, surrounded by three bidentate chelating ligands, that is, two pao-and o
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19

Konidaris, Konstantis F., Eugenia Katsoulakou, Michalis Kaplanis, et al. "A tetrahedron in a cube: a dodecanuclear ZnII benzoatecluster from the use of 2-pyridinealdoxime." Dalton Trans. 39, no. 19 (2010): 4492–94. http://dx.doi.org/10.1039/b918885a.

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20

Ha, Kwang. "Crystal structure of dichlorobis(2-pyridinealdoxime-N,N′)-manganese(II) dihydrate, MnCl2(C6H6N2O)2 · 2H2O." Zeitschrift für Kristallographie - New Crystal Structures 225, no. 4 (2010): 651–52. http://dx.doi.org/10.1524/ncrs.2010.0284.

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21

Shi, Quan, Zhi-Cheng Tan, Bo Tong, et al. "Low-temperature heat capacity and standard molar enthalpy of formation of crystalline 2-pyridinealdoxime (C6H6N2O)." Journal of Chemical Thermodynamics 39, no. 5 (2007): 817–21. http://dx.doi.org/10.1016/j.jct.2006.09.016.

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22

Zheng, Lina, Suyun Zhang, Kai Li, et al. "Mixed bridged dinuclear Ni(II) complex incorporating 2-pyridinealdoxime ligand: Synthesis, crystal structure and magnetic property." Journal of Molecular Structure 984, no. 1-3 (2010): 153–56. http://dx.doi.org/10.1016/j.molstruc.2010.09.020.

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23

Nepovimova, E., J. Korabecny, R. Dolezal, et al. "A 7-methoxytacrine–4-pyridinealdoxime hybrid as a novel prophylactic agent with reactivation properties in organophosphate intoxication." Toxicology Research 5, no. 4 (2016): 1012–16. http://dx.doi.org/10.1039/c6tx00130k.

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24

Solodenko, Wladimir, Christoph Brochwitz, Rudolf Wartchow, et al. "2-Pyridinealdoxime, a new ligand for a Pd-precatalyst: Application in solid-phase-assisted Suzuki–Miyaura reaction." Molecular Diversity 9, no. 4 (2005): 333–39. http://dx.doi.org/10.1007/s11030-005-7457-y.

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25

Allan, J. R., and B. McCloy. "Thermal, spectral and magnetic studies of the chloro complexes of manganese, cobalt, nickel and copper with 3-pyridinealdoxime." Thermochimica Acta 211 (December 1992): 85–91. http://dx.doi.org/10.1016/0040-6031(92)87009-y.

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26

Allan, J. R., and A. D. Paton. "Preparation, structural, thermal and electrical studies of the chloro complexes of cobalt, nickel and copper with 4-pyridinealdoxime." Thermochimica Acta 228 (November 1993): 71–78. http://dx.doi.org/10.1016/0040-6031(93)80275-f.

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27

Okuno, Sou, Koichi Sakurada, Hikoto Ohta, et al. "Blood–brain barrier penetration of novel pyridinealdoxime methiodide (PAM)-type oximes examined by brain microdialysis with LC-MS/MS." Toxicology and Applied Pharmacology 227, no. 1 (2008): 8–15. http://dx.doi.org/10.1016/j.taap.2007.09.021.

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28

Amani, Vahid, Darioush Sharafie, Naghmeh Faal Hamedani, and Mohamad Naseh. "Zinc(II) and mercury(II) iodide complexes containing 2-pyridinealdoxime compound: synthesis, characterization, crystal structure determination and DFT study." Journal of the Iranian Chemical Society 17, no. 2 (2019): 441–51. http://dx.doi.org/10.1007/s13738-019-01780-6.

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29

Radić, Zoran, Rakesh K. Sit, Zrinka Kovarik, et al. "Refinement of Structural Leads for Centrally Acting Oxime Reactivators of Phosphylated Cholinesterases." Journal of Biological Chemistry 287, no. 15 (2012): 11798–809. http://dx.doi.org/10.1074/jbc.m111.333732.

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We present a systematic structural optimization of uncharged but ionizable N-substituted 2-hydroxyiminoacetamido alkylamine reactivators of phosphylated human acetylcholinesterase (hAChE) intended to catalyze the hydrolysis of organophosphate (OP)-inhibited hAChE in the CNS. Starting with the initial lead oxime RS41A identified in our earlier study and extending to the azepine analog RS194B, reactivation rates for OP-hAChE conjugates formed by sarin, cyclosarin, VX, paraoxon, and tabun are enhanced severalfold in vitro. To analyze the mechanism of intrinsic reactivation of the OP-AChE conjugat
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30

Radić, Zoran, Trevor Dale, Zrinka Kovarik, et al. "Catalytic detoxification of nerve agent and pesticide organophosphates by butyrylcholinesterase assisted with non-pyridinium oximes." Biochemical Journal 450, no. 1 (2013): 231–42. http://dx.doi.org/10.1042/bj20121612.

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In the present paper we show a comprehensive in vitro, ex vivo and in vivo study on hydrolytic detoxification of nerve agent and pesticide OPs (organophosphates) catalysed by purified hBChE (human butyrylcholinesterase) in combination with novel non-pyridinium oxime reactivators. We identified TAB2OH (2-trimethylammonio-6-hydroxybenzaldehyde oxime) as an efficient reactivator of OP–hBChE conjugates formed by the nerve agents VX and cyclosarin, and the pesticide paraoxon. It was also functional in reactivation of sarin- and tabun-inhibited hBChE. A 3–5-fold enhancement of in vitro reactivation
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31

Papatriantafyllopoulou, Constantina, Theocharis C. Stamatatos, Constantinos G. Efthymiou, et al. "A High-Nuclearity 3d/4f Metal Oxime Cluster: An Unusual Ni8Dy8“Core−Shell” Complex from the Use of 2-Pyridinealdoxime." Inorganic Chemistry 49, no. 21 (2010): 9743–45. http://dx.doi.org/10.1021/ic101581g.

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32

Sit, Rakesh K., Zoran Radić, Valeria Gerardi, et al. "New Structural Scaffolds for Centrally Acting Oxime Reactivators of Phosphylated Cholinesterases." Journal of Biological Chemistry 286, no. 22 (2011): 19422–30. http://dx.doi.org/10.1074/jbc.m111.230656.

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We describe here the synthesis and activity of a new series of oxime reactivators of cholinesterases (ChEs) that contain tertiary amine or imidazole protonatable functional groups. Equilibration between the neutral and protonated species at physiological pH enables the reactivators to cross the blood-brain barrier and distribute in the CNS aqueous space as dictated by interstitial and cellular pH values. Our structure-activity analysis of 134 novel compounds considers primarily imidazole aldoximes and N-substituted 2-hydroxyiminoacetamides. Reactivation capacities of novel oximes are rank orde
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33

Mancin, Fabrizio, Paolo Tecilla, and Umberto Tonellato. "Metallomicelles Made of Ni(II) and Zn(II) Complexes of 2-Pyridinealdoxime-Based Ligands as Catalyst of the Cleavage of Carboxylic Acid Esters†." Langmuir 16, no. 1 (2000): 227–33. http://dx.doi.org/10.1021/la9909594.

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34

Milios, Constantinos J., Elena Kefalloniti, Catherine P. Raptopoulou, et al. "2-Pyridinealdoxime [(py)CHNOH] in manganese(II) carboxylate chemistry: mononuclear, dinuclear, tetranuclear and polymeric complexes, and partial transformation of (py)CHNOH to picolinate(−1)." Polyhedron 23, no. 1 (2004): 83–95. http://dx.doi.org/10.1016/j.poly.2003.09.009.

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35

da Silva, Jorge Alberto Valle, Eugenie Nepovimova, Teodorico Castro Ramalho, Kamil Kuca, and Tanos Celmar Costa França. "Molecular modelling studies on the interactions of 7-methoxytacrine-4-pyridinealdoxime with VX-inhibited human acetylcholinesterase. A near attack approach to assess different spacer-lengths." Chemico-Biological Interactions 307 (July 2019): 195–205. http://dx.doi.org/10.1016/j.cbi.2019.05.019.

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36

da Silva, Jorge Alberto Valle, Eugenie Nepovimova, Teodorico Castro Ramalho, Kamil Kuca, and Tanos Celmar Costa França. "Molecular modeling studies on the interactions of 7-methoxytacrine-4-pyridinealdoxime, 4-PA, 2-PAM, and obidoxime with VX-inhibited human acetylcholinesterase: a near attack conformation approach." Journal of Enzyme Inhibition and Medicinal Chemistry 34, no. 1 (2019): 1018–29. http://dx.doi.org/10.1080/14756366.2019.1609953.

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37

Neumann, Kiel D., Joseph E. Blecha, Thomas R. Hayes, et al. "Radiosynthesis, ex Vivo Biodistribution, and in Vivo Positron Emission Tomography Imaging Evaluations of [11C]2-Pyridinealdoxime Methiodide ([11C]2-PAM): A First-In-Class Antidote Tracer for Organophosphate Intoxication." ACS Chemical Neuroscience 9, no. 12 (2018): 3007–14. http://dx.doi.org/10.1021/acschemneuro.8b00212.

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38

Stamatatos, Theocharis C., Eleanna Diamantopoulou, Anastasios Tasiopoulos, et al. "Enneanuclear Ni(II) complexes from the use of the flexible ligand 2-pyridinealdoxime: The nature of the inorganic anion does not affect the chemical and structural identity of the cationic cluster." Inorganica Chimica Acta 359, no. 12 (2006): 4149–57. http://dx.doi.org/10.1016/j.ica.2006.04.021.

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39

Timperley, Christopher M., R. Eric Banks, Ian M. Young, and Robert N. Haszeldine. "Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning." Journal of Fluorine Chemistry 132, no. 8 (2011): 541–47. http://dx.doi.org/10.1016/j.jfluchem.2011.05.028.

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40

Timperley, Christopher M., R. Eric Banks, Ian M. Young, and Robert N. Haszeldine. "ChemInform Abstract: Synthesis of Some Fluorine-Containing Pyridinealdoximes of Potential Use for the Treatment of Organophosphorus Nerve-Agent Poisoning." ChemInform 42, no. 48 (2011): no. http://dx.doi.org/10.1002/chin.201148147.

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41

Jaszewski, A. R., J. Jezierska, M. Krowicka, and E. Kalecińska. "EPR and density functional studies on 3-pyridylmethaniminoxy radical:1H hyperfine couplings as a structural criterion for iminoxyls derived from pyridinealdoximes." Applied Magnetic Resonance 18, no. 1 (2000): 85–100. http://dx.doi.org/10.1007/bf03162101.

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42

Stamatatos, Theocharis C., Khalil A. Abboud, Spyros P. Perlepes, and George Christou. "The highest nuclearity metal oxime clusters: Ni14 and Ni12Na2 complexes from the use of 2-pyridinealdoximate and azide ligands." Dalton Transactions, no. 35 (2007): 3861. http://dx.doi.org/10.1039/b708189h.

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43

Wang, Jin-Hua, Mohammad Khurram Javed, Jia-Xin Li, Yi-Quan Zhang, Zhaoyang Li, and Masahiro Yamashita. "Ferromagnetically coupled single-chain magnets exhibiting a magnetic hysteresis of 0.42 Tesla in cyano-bridged FeIII2MII (M = Ni, Fe) coordination polymers." Dalton Transactions, 2023. http://dx.doi.org/10.1039/d3dt01043k.

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The synthesis, single-crystal structures and magnetic properties of two new double-zigzag-chain cyano-bridged heterobimetallic {[MІІ(Py-NOH)2][FeІІІ(Tp*)(CN)3]2}·H2O ([FeIII2MII]) (Py-NOH = 4-pyridinealdoxime, Tp* = tris(3,5-dimethylpyrazol-1-yl)borohydride, M = Ni (1), Fe (2)) compounds are reported....
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44

Ha, Kwang. "Crystal structure of dichloro(2-pyridinealdoxime- k2N,N')platinum(II), PtCl2(C6H6N2O)." Zeitschrift für Kristallographie - New Crystal Structures 226, no. 4 (2011). http://dx.doi.org/10.1524/ncrs.2011.0221.

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45

Ha, Kwang. "Crystal structure of dichloro(2-pyridinealdoxime- k2N,N')palladium(II), PdCl2(C6H6N2O)." Zeitschrift für Kristallographie - New Crystal Structures 226, no. 4 (2011). http://dx.doi.org/10.1524/ncrs.2011.0233.

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46

Ha, Kwang. "Crystal structure of dibromobis(2-pyridinealdoxime-k2N,N')- manganese(II), MnBr2(C6H6N2O)2." Zeitschrift für Kristallographie - New Crystal Structures 226, no. 4 (2011). http://dx.doi.org/10.1524/ncrs.2011.0232.

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47

Solodenko, Wladimir, Christoph Brochwitz, Rudolf Wartchow, et al. "2-Pyridinealdoxime, a New Ligand for a Pd-Precatalyst: Application in Solid-Phase-Assisted Suzuki—Miyaura Reaction." ChemInform 37, no. 21 (2006). http://dx.doi.org/10.1002/chin.200621101.

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48

Xiang, Runan, Shihan Wang, Peisen Liao, et al. "Electrocatalytic Synthesis of Pyridine Oximes using in Situ Generated NH2OH from NO species on Nanofiber Membranes Derived from NH2‐MIL‐53(Al)." Angewandte Chemie International Edition, September 20, 2023. http://dx.doi.org/10.1002/anie.202312239.

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Pyridine oximes producing from aldehyde or ketone with hydroxylamine (NH2OH) have been widely applied in pharmaceutics, enzymatic and sterilization. However, the important raw material NH2OH, exhibits corrosive and unstable properties, leading to substantial energy consumption during storage and transportation. Herein, this work presents a novel method for directly synthesizing highly valuable pyridine oximes using in situ generated NH2OH from electrocatalytic NO reduction with well‐design nanofiber membranes (Al‐NFM) derived from NH2‐MIL‐53(Al). Particularly, 2‐pyridinealdoxime, the precursor
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49

Xiang, Runan, Shihan Wang, Peisen Liao, et al. "Electrocatalytic Synthesis of Pyridine Oximes using in Situ Generated NH2OH from NO species on Nanofiber Membranes Derived from NH2‐MIL‐53(Al)." Angewandte Chemie, September 20, 2023. http://dx.doi.org/10.1002/ange.202312239.

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Pyridine oximes producing from aldehyde or ketone with hydroxylamine (NH2OH) have been widely applied in pharmaceutics, enzymatic and sterilization. However, the important raw material NH2OH, exhibits corrosive and unstable properties, leading to substantial energy consumption during storage and transportation. Herein, this work presents a novel method for directly synthesizing highly valuable pyridine oximes using in situ generated NH2OH from electrocatalytic NO reduction with well‐design nanofiber membranes (Al‐NFM) derived from NH2‐MIL‐53(Al). Particularly, 2‐pyridinealdoxime, the precursor
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