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Nature and Reactions Op the Complexes Op Nickel

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Nature and Reactions Op the Complexes Op Nickel NATURE AND REACTIONS OP THE COMPLEXES OP NICKEL, PALLADIUM, AND PLATINUM WITH 2-PYRTDTNA LDOXIME AND DIMETHYLGLYOXIME DISSERTATION Presented In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of the Ohio State Uhlversity By RONALD ALFRED KRAUSE, B. Sc. ******* The Ohio State University 1959 Approved by Adviser Department of Chemistry ACKNOWLEDGMENTS It is with extreme pleasure that the author wishes to thank Dr. Daryle H. Busch for his council, encouragement, and enthusiasm which made the years in graduate school meaningful. To Dr. Quentin Van Winkle the author is very grateful for suggestions and the use of the ultracentrifuge both of which were extremely helpful in the completion of some of these investigations. The author wishes to thank Dr. Sheldon G. Shore and Mr. Selwyn H. Rosenthal for kindly providing the use of their dry box, necessary in a portion of this work. Dr. Melvin L. Morris, Mr. Donald C. Jicha, and Mr. William R. Findley are to be thanked for obtaining all the infrared spectra reported in this dissertation; Mr.! Jicha is also to be thanked for supplying one of the compounds used for comparison. The National Institutes of Health is to be thanked for a Research Fellowship supporting the author during the latter part of the work reported herein. Mrs. Robert Holsinger, Jr. prepared the drawings and Mrs. Leo Moore typed the dissertation; the author is grateful to them for these services. And above all the author wishes to thank his wife, Kay, not only for typing the first draft of the dissertation but for her help and encouragement during the years at The Ohio State University. CONTENTS Chapter Page I. 2-PYRIDINALD0XIME COMPLEXES OP NICKEL(ll), PALLADIUM(II) , AND PLATINUM(II) .......... 1 A. Introduction........................... 1 1. Complexes of o£-DIoximes ..... 3 2. Complexes of 2,2 -Bipyridine . 15 3. Complexes of Bidentate Amine Oximes 16 B. Experimental ..........................18 1. Preparation of L i g a n d ..............18 2. Nickel C o m p o u n d s .............. 19 3. Palladium and Platinum Compounds . 25 4. Physical Measurements..............27 C. Results and D i s c u s s i o n ............... 28 1. Nickel(ll) Complexes ............ 29 2. Palladium(ll) and Platinum(ll) Complexes ....................44 D. Discussion of Infrared Spectra .... 47 II. REACTIONS OP NICKEL(il), PALLADIUM(II), AND PLATINUM(II) COMPLEXES OP 2-FYRTD1NAL- DOXIME AND DIMETHYLGLYOXIME................85 A. Introduction..........................85 1. Reactions of Coordinated Ligand . 86 2. Reactions of the Central Metal Atom with Halogens...................... 87 B. Experimental ......................... 93 1. Preparation of Dimethylglyoxime Complexes.......................... 93 2. Reaction of 2-Pyridinaldoxime Complexes with B r o m i n e ............95 3. Reaction of Dimethylglyoxlme Complexes with B r o m i n e ............97 4. Reaction of Complexes with Reagents Containing an Active Halogen .......................... 99 5. Physical Methods .................103 C. Results and Discussion ....... .104 1. Reactions with Compounds Containing Active Halogen ....... 106 2. Reactions with B r o m i n e ...........109 ill ♦ iv CONTENTS (Contd.) Chapter Page III. SUMMARY........................................ 116 APPENDIXES I. Magnetic Susceptibility Measurements ......... 122 II. Temperature Dependence of the Magnetic Susceptibility of [Nl(P0X)2 ] 127 III. Infrared Absorption Spectra of the Nickel(il), Palladium(II), Platinum(ll), and Platlnum(IV) Complexes of Dimethylglyoxime ................. 129 BIBLIOGRAPHY.......................................... 139 AUTOBIOGRAPHY........................................ 1^5 LIST OP TABLES Table Page 1. The Use of Nickel Derivatives in the Confirmation of Oximes ........................ 4 2. Magnetic Moments and Conductivities of Complexes of 2-Pyridinaldoxime .............. 3 0 3. infrared Absorption Spectra and Assignments for Complexes of 2-Pyridinaldoxime. Complexes Containing Unionized Ligand.................. 4 9 4. infrared Absorption Bands and Assignments for Complexes of 2-Pyridinaldoxime. Complexes Having One Ligand Proton Ionized .............. 56 5. Infrared Absorption Spectra and Assignments for Complexes of 2-Pyridinaldoxime. Uncharged Complexes . .......................... 61 6 . Infrared Absorption Spectra and Assignments for Complexes of 2-Pyridinaldoxime. Reaction Products......................................... 67 7. Magnetic Susceptibilities of Nickel(il) Complexes of2-Pyridinaldoxime .................125 8 . Standardization of Magnetic Susceptibility Apparatus....................................... 126 9. Temperature Dependence of the Magnetic Susceptibility of [Ni(P0X)2 ] . ........... .128 10. Infrared Absorption Spectra of Nickel,. Palladium, and Platinum Complexes of Dimethyl- glyoxime .................................... 130 v LIST OP FIGURES Figure Page p 1. Configurations of d° Ions, Their Magnetic Moments, and Their Crystal Field Splittings . 11 2. Job Method of Continuous Variations, [Ni(POX)(HPOX)]I and AgNO^ .................... 35 3. Ultraviolet Absorption Spectrum of Ni(P0X)2HI Solutions and Their Interaction with Silver Ion 37 4. Temperature Dependence of Magnetic Susceptibility of [Ni(P0X)2 ] 42 5. System Pd++ -HPOX, Titrated with N a O H ...... 46 6 . Infrared Absorption Spectrum of HPOX and of [Ni(HP0X)3 ]l2 .2H20 . 53 7. Infrared Absorption Spectrum of [Ni(HP0X)oIo ] and [NI(HP0X)2C12] ......................... 54 8 . Infrared Absorption Spectrum of [Ni(HPOX)o (CH3COO)2 ] and [Ni(POX)(HPOX)(CH3COO)(HgOfi. 55 9. Infrared Absorption Spectrum of [Ni(POX)(HPOX)(py)2 ]I and [Ni(POX)(HPOX)Jl . 59 10. Infrared Absorption Spectrum of [Pd(POX) (HPOX) ]C1 60 1 1 . Infrared Absorption Spectrum of [Ni(P0X)opy] and [Ni(P0X)2 (py)2 ] ........................ 64 12. Infrared Absorption Spectrum of [NifPOX)^] and [Pd(P0X)2 ] i . 65 13. Infrared Absorption Spectrum of [Pt(P0X)2 ]. 66 14. Infrared Absorption Spectrum of [Pt(P0X)2Br2 ] . 71 15. Infrared Absorption Spectrum of [Pd(P0X)2Br9 3 and of [Pd(P0X)2 ] and Br2 Reaction Product. 72 16. Infrared Absorption Spectrum of [Pd(P0X-C0CH3 )Cl2 ] and [Pd(P0X)Cl]2 ........... 73 vl vii LIST OP FIGURES (Contd.) Figure Page 17. Infrared Absorption Spectrum of [Pt(P0X-C0CH3 )2 ]Cl2......... ................ 74 18. Infrared Absorption Spectrum of [Pd(POX-COCgH5 )Cl23........... 75 19. Infrared Absorption Spectrum of[Pd(DMG)0 ] and [Pt(DMG)2] ........................d . 133 20. Infrared Absorption Spectrum of [Pt(DMG)2Br2] ............................... 134 21. Infrared Absorption Spectrum of CHC1- In­ soluble Product of Reaction of [Nl(DMG)2 ] and BrP and Infrared Absorption Spectrum of [Ni(HJMJ)2Br2 ]................................. 135 22. Infrared Absorption Spectrum of [Pt(HDMG)Cl2 ] and [ Pd(HDMG)Br2 ] ...............136 23. Infrared Absorption Spectrum ofNi (HDMSjCl^I^O 137 I. 2-PYRIDINALDOXIME COMPLEXES OP NICKEL(II), PALLADIUM(II), AND PLATINUM(II). A. Introduction The nickel(II), palladium(ll), and platinum(ll) complexes of 2-pyridinaldoxime (HPOX) (structure I) are the subject of this section of the dissertation. 2-Pyridinaldoxime was first prepared by Lenart1 in 1914 (as a derivative of the aldehyde), but no attempt was made to prepare its complexes. 2-Pyridinaldoxime shows structural features of both dimethylglyoxime (HDMGr) h 3c OH- \ / J c c HO—N// \N-OH ■N 'N II III (structure II) and 2,2'-bipyridlne (bipy) (structure III), in that it has an oxime function to a second donor group (as in HDMG), and in that the second donor group is a 2-substituted pyridine ring, such as exists in 2 ,2 *- bipyridine. 2-Pyridinaldoxime also shows some similarity to 2-methyl-2-amino-3-butanone oxime (AOH) (structure IV) C H, CHcj n r- -Clio // r H 0— N NH2 IV in that both compounds are amine oximes, the amine in one being aromatic, that in the other, aliphatic. This amine oxime can be considered as a composite of HDMG (structure II) and ethylenediamine (en) (structure V). H o C CH0 *7 h 2 n n h 2 V Two ligands similar to 2-pyridinaldoxime, and some of their complexes, have been reported. Tschugaeff2 first prepared palladium(II) and platinum(II) compounds of phenyl-fit-pyridyl ketoxime (structure VI); Sen, recently, reported the use of this ligand for the spectro- 3 4 photometric determination of palladium(ll). Emmert and Diehl-* reported the reaction of methyl-^C-pyridyl ketoxime (structure VII) with nickel(ll). Both of these ligands have been studied only in a cursory manner. The investigation of the complexes of HPOX reported in this ,c 6h5 / 6 5 / k3 V / 0H S * / 0H VI VII dissertation represents the first detailed study of a ligand of this class. The only experimental work which has been reported on complexes of HPOX Involves the equilibria of the iron(ll) derivatives in aqueous solution^ 1. Complexes of qt-Dioximes.— Since Tschugaeff dis­ covered the complexes of o^-dioxinies, ^ the interaction of oximes with metal Ions has been of considerable interest to chemists. Tschugaeff also discovered the bright red compound [Ni(DMG)2 ] and published the first paper O utilizing it for the quantitative determination of nickel. Since Tschugaeff*s time the nickel, palladium, and plati­ num complexes of many oximes have been studied. Organic chemists have utilized color reactions with nickel to confirm the nature of oxime derivatives (Table l). Analytical chemists have used oximes as reagents for the determination of nickel, palladium, and platinum, and inorganic chemists have studied
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