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SYNTHESIS, Characferiza TION, and APPROACHES to the ANAL SYNTHESIS, CHARACfERIZATION, AND APPROACHES TO THE ANALYSIS BY HPLC-THG-AAS OF TRIMETIiYLSELENONIUM, SELENONIUMCHOLINE AND SELENONIUMACETYLCHOLINE CATIONS. sv ALEXIS HUYGHUES-DESPOINTES ( © A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfillment of the requirements for the degree of Master of Science Department of Food Science and Agricultural Chemistry. McGiII university, Macdonald Campus, Montreal, Quebec March,1991 i.. Suggested short title: Synthesis and analysis of selenonium cations by HPLC·THG-AAS. ABSTRAcr Selenonium cations are electron deficient spedes in which the central selemum atom is bonded to three carbon chains (aryl or alkyl). Trirnethylselenonium iodide was synthesized elther by the methOlJ of Khun et al. (1986) or electrochernically. Se!cnoniumcholine and selenomumacetylchohne were synthesized by reaction of rnethyllithium with metallic selenium to produce methylselenohtlllum wlllch was, in turn, reacted with the appropriate alkylbromide. The selenide thus formed was further methylated at the selenium atom with methyl iodide in methanol in the presence of sodium tetraphcnylborate. Aftcr seve raI recrystallizations the selenonium analytes were charactenzed by AAS. Fr-IR. IH-NMR. 13e_ NMR, F AB· MS and LAMMA spectroscopic techniques and used as standards for analyucal method!> development. The analysis was performed by high performance Iiquid chromatography wlth.atomlc ab!>orptlOll detection. The chromatography on a cynopropyl silica bonded phase was optlmlzed for mobIle phase composition by response surface analysis. The resulting surface response plots permltted a dltfcrentlatloll between the mechanisms of action of two mobile phase modlfiers: tnethylamme and tnmethybulfonJUm iodide. The improvement in chromatographie efficiency resulted ln two to three fold dccrea!>c ln the Ilmlt of detection. An extraction procedure WIth Iiquefied phenol was evaluated for the determll1.ltlOn. by HPLC-AAS, of traces of selenonium catIons in biologlcal sampI es. The advantages and !>holtcommg!> of the HPLC-THO-AAS approach are discussed. RESUME Les cations de sélénonium sont des espèces défi-::itaires en électron03, ou l'atome de sélénium central est lié à trois chaines carbonnées de type aryl ou a1kyI. La méthode de Knun et col. (1986) ainsi qu'un procédé électrochimique furent utilisés pour réaliser la synthèse de l'iodure de tnméthylsélénomum. La sélénoniumcholine et la sélé'loniumacétylcholine furent générées grâce à l'action du méthyllithium sur le sélér.ium métallique donnant du méthylsélénolitium; ce dernier étant par la sUite mis en présence de l'alkylbromide approprié. Le sélénide formé fut ensuite méthylé, dans du méthanol, au nIveau de l'atome de sélémum avec de l'iùdure de méthyle en présence de tétraphénylborate de sodium. Après une série de recrystallisations-cha.actérisations par diverses téchniques spéctroscoplques (SAA, IR-TF, RMN)H, RMN)3C, SM·FAB et LAMMA), ces divers Ions sélénonium furent uhtisés pour le développement de la méthode analytique. La séparation et la quantification de ces produits furent réalisées par une chromatographie lIquide haute p"rformance (HPLC) couplée à un spectrophotomètre d'absolption atomique (SAA). L'optimisation de la chromatographIe, dont le support était une sIlice gréffée par des groupements cyanopropyl, fut permise grâce à l'étude de réponses de c;urface. Ces analyses statistiques ont également permis d'élUCider le méchanisme d'action de deux substances modifiant la phase mobIle: la tnéthylamme et le triméthylsulfomum IOdide. L'amélioratIOn de l'éfficacité de la chromatograplue a diminué la lImite de détection d'un facteur pouvant varIe; de deux à trois. La procédure d'extraction à partir de phénol liqUide fut évaluée par la quantification de traces de cations de sélénium dans des entités bIOlogiques par le système HPLC·SAA. Les avantages et les inconvenients de cette méthode furent ensUite discutés. ü ACKNOWLEDGEMENTS The: <Luthor wishes to express bis gratitude to Dr. W.D. Marshall, supervlsor and research director, who suggested this re8.!arch and provided guidance, ad\:ce, and support throughout the course of this study. 1,'he, author is also indebted to Dr. J.-S. Blrus for lus invaluable advlce and expertise. The a'\tthor would also like to thanks prof L Van Vaeck for the LAMMA !>pectra and S. MandevIlle for 'lis preciolls help Wlth the FT-IR. The author is particularly gratefui for the help and friendshJp that Georges·Mane Momplalslr, and Tian Lei. fellow-workers, proVlded constantly. iii TABLE OF CONTENT ( Page ABSTRA cr........................ ___.. ____ .................... _ ................. _ ......................................................................................i RESUME ................................ __....... _...................... _ ...................... - .................................................................................... ii ACKN OWLEDG EMENTS _........ _ ................. _..... __ ........................................................................................................ iii TABLE OF CONffiNT .... _ ......... __.................... _ ....................... _._............................................................................... iv LIST 0 F TABLES .......... _. __... __ .. _ ...................... _._ ................. _ .................................................................................... ix LIST OF FIGURES ......... _ ........................................... m ..........__ ................................................................................ xi CHAPTER: 1: INTRODUcrION ._......................................................... __................................................................................ 1 1.1. GENERAL CONSIDERA TIONS .................... __.......... _................................................................... 2 1.2. s,ELENJUM COMPOUNPS PRESENT IN FOOPS....................................................................... ,3 1.3. METABOLISM OF SELENIUM ...................... _ .................................................................................. 5 1.2. TOXICITX OF SOME SELENWM COMPOUNPS ....................................................................... 6 ( 1.3. BIOA V AILABILITY OF SOME SELENlJ,lM COMPOUNDS AND SeME FOODS AND FEED~ ........................................................................................................6 II: SYNTHESIS OF SELENONJUM COMPOUNDS............................................................................. 11 2.1. nIE PREPARATION ANDPROPERTIES OFSELENONIUMCOMPOUNDS: A LrrERATURE REVIEW .............................. _.................................................................................... 12 2.1.1. METHODS OF SYNTHESIS ........ M ........._ ............................................................................... 12 2.1.1.1. REACI10N OFDIALKYLSELENlDES (R2SE) wrrn ALKYL HALIDES (RX) ..................................................................................... 12 2.1.1.1.1. Symmetncal Selenides .............. _ ................................................................................ 12 2.1.1.1.1.1. R2Se + RX -----> R3Se+X- ............................................................................... 12 2.1.1.1.1.2. R2Se + R'X ----~ R'2R'Se+X· ........................................................................... 13 2.1.1.1.2. Unsymmetrical Selenides (RR'§e) ......................................................................... 13 ( 2.1.1.1.2.1. R'SeR t RX -----> R2R'Se+X· ......................................................................... 13 2.1.1.17_2. R'SeR t R"X ----> RR'R·Se+X· ...................................................................... 16 2.1.1.1.3. Cyclic Selemdes with Alkyl Halides ........................................................................ 17 iv TABLE OF CONTENT (contmued) Page 2.1.1.2. REACf!ON OF ORGANIC SELENIDES WTIlI OrnER ALKYLA TING AGEN1'S ................................................................. 18 2.1.1.21. Dimethylsulfate.......................... _ ................................................................................. 18 2.1.1.22. Triflate Salts. ................................................................................................................... 19 2.1.1.2.3. Miscellaneous ................................................................................................................. 19 2.1.1.3. REACTION OF OTHER ORGANIC SE SPECIES ........................................... 19 2.1.13.1. Diselenides and/or Selenols ...................................................................................... 19 2.1,1.3.2 Selenoxides ..................................................................................................................... 20 2.1.1.4. REACI10N OF INORGANIC SE SPECIES............................................................ 20 2.1.1.4.1. Selenium Halides ................. _ ..... ~_ ............................................................................ 20 2.1.1.4.2. ElcmentaJ Selenium ..................................................................................................... 22 2.1.1.4.3. Sodium Selenite ............................................................................................................ 22 2.1.2. REACfIyrrœs OF SELENONIUM COMPOUNDS .................................................... 22 2.1.2.1. CHEMICAL PROPERTIES ............................................................................................
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