ABSTRACTHarlemChildrenSociety摘要哈莱姆儿童协会

《ABSTRACTHarlemChildrenSociety摘要哈莱姆儿童协会》由会员分享，可在线阅读，更多相关《ABSTRACTHarlemChildrenSociety摘要哈莱姆儿童协会（19页珍藏版）》请在装配图网上搜索。

1、Creating an Ion&Molecular Sensor By Combining Phenyl Mercaptoacetamide&Benzyl Mercaptoacetamide Ligands with Preferable MetalsSubmitted by:Chris RocaMentor:Duncan Quarless,Ph.D.Undergraduate Asst.Mentor:Alicia BowenABSTRACTlPhenyl mercaptoacetamide(PMA)&Benzyl mercaptoacetamide(BMA)were synthesized

2、to observe their imitative relevance for fabricating the structure and reactivity of metallocysteinate proteins that are involved in metal transport.lThese ligands were used to observe if the type of reaction that takes place between them and the metal cations,which are Zinc(Zn2+)and Cobalt(Co2+),ca

3、n produce an ion detecting molecule.lXylenol Orange was used as a color indicator to determine the extinction(metal concentration dependence)which is used from Beers law A=EBC and examine the visible spectroscopy of the various solutions,which determines the relative concentration of complexed and f

4、ree indicators.lAlthough no major results are yet found,zinc appears to be the least discriminate of the metal cations with respect to xylenol orange.Cobalt showed a lower extinction than Zinc which meant more concentration was needed than Zinc.lThe purpose of such an experiment is to see if these l

5、igands can be an alternative for ion detection when combined with a metal,which for the moment seems to be Zinc.INTRODUCTIONl Ion recognition continues to be a major research goal for many supramolecular chemist groups around the world.l Phenyl mercaptoacetamide(PMA)&Benzyl mercaptoactamide(BMA)are

6、ligands or in other words they are a molecule that bonds to the central metal atom of a compound.l What is expected to happen is that the ligands,BMA and PMA,would react with the metals,Zinc(Zn)and Cobalt(Co),to form a molecule that detects specific ions when the two come into contact.l If successfu

7、l this experiment can help produce an ion detecting agent that is a novel sulfur based ligand,and these assays will likely have relevance in analytical,environmental chemistry,as well as biomedical imaging and drug discovery.MATERIALSCHEMICALSl Anilinel Benzylaminel Thioglycolic acid(mercaptoacetic

8、acid)l Cobalt acetatel Zinc acetatel pH 5 bufferl MethanolLAB EQUIPMENTl Thermometersl Weighing scalesl Assorted glassware(Volumetric flasks,Erlenmeyer flasks,Buchner funnels,etc)l Ultra violet Light(UV/vis)spectrophotometerl Infrared(IR)spectroscopy apparatusl Nuclear Magnetic Resonance(NMR)Spectro

9、scopy apparatusSYNTHESIS OF BMA&PMABenzyl MercaptoacetamidePhenyl MercaptoacetamideMETHODSl BMA&PMA were synthesized from benzyl amine and aniline,respectivelyl Samples were recrystallized from methanoll Checked melting point of samplesl Tested purity of samples using GC-MS(gas chromatograph with ma

10、ss spectrophotometer)l Created pH 5 buffer for use in metal reactionsl Created metal solutions using zinc acetate and cobalt acetate in methanoll Xylenol Orange indicator was added to metal solutions which were then tested in uv/vis spectrophotometer to determine the extinction coefficients for meta

11、l xylenol orange complexesl Tested BMA&PMA using 1H NMR(nuclear magnetic resonance)to test the purity of solutions,and to characterize the compoundsl Tested for impurities and characterization using infrared spectroscopyRotating Around the Carbon-Amide BondRESULTSl No major results yet foundl In the

12、 UV/vis spectrophotometer Zinc was shown to have a more drastic extinction pattern in XO than Cobalt did in XOl Zinc is a better candidate than Cobalt for such an experimentl Impurities were seen in the BMA&PMA when tested using IR spectroscopyl The NMR machine is currently malfunctioning,therefore,

13、our samples have yet to be testedFUTURE WORKSl Other metals will be tested as well such as Copper(Cu2+),Lead(Pb2+),and Mercury(Hg2+)l The NMR machine will be finally used soon,so we can test magnetic resonance with BMA&PMAl A better synthesis of PMA&BMA to try to make them 100%pure REFERENCESlConrad

14、ie,J;Quarless,D.A;Hsu,H-F;Harrop,T.C;Lippard,S.J;Koch,S.A;Ghosh,A“Electronic structure and FeNO conformation of nonheme iron-thiolate-NO complexes:A combined experimental and DFT study,”J.Am.Chem.Soc.2007,(in press).lMorlok,M M;Janak,K E;Zhu,G;Quarless,D A;Parkin,G“Intramolecular N-H.S Hydrogen Bond

15、ing in the Zinc Thiolate Complex(TmPh)ZnSCH2C(O)NHPh:A Mechanistic Investigation of Thiolate Alkylation as Probed by Kinetics Studies and by Kinetic Isotope Effects,”J.Am.Chem.Soc.2005,127,14039.lParkin,G.;Morlok,M.M.;Janak,K.E.;Melnick,J.G.;Zhu,G.;Docrat,A.;Quarless,Jr.,D.A.,“Chalcogenolate complex

16、es of zinc in a sulfur rich coordination environment employing tris(2-mercaptoimidazolyl)hydroborato ligation,TmRZnEX(E=O,S,Se,Te):Synthetic analogues for modeling the mechanism of action of the Ada DNA repair protein,”Inorganic Paper 84,229th National Meeting of the American Chemical Society,San Di

17、ego,CA;March 2005.lQuarless,D.A.;Bridgewater,B.M.;Parkin,G.“Tris(mercaptoimidazolyl)hydroborato zinc mercaptoacetamides:ligand exchange and methyl group transfer.”Poster Presentation,Gordon Inorganic Conference.Newport,RI 2002.lBhandari,C.s.Infrared and NMR Spectral Studies of Mercaptoacetamides.Bul

18、letin De Acadenie Polonaise Des Sciences.Serie Des Sciences Chimiques 20(1972):91-100.lBhandari,C.s.Preparation and Electronic Spectra of Mercaptoacetamides.Journal Fur Praktische Chemie 313(1971):849-854.Abstract.Journal Fur Praktische Chemie 313(1971):5.lGiles,Niroshini M.,Aaron B.Watts,Jennifer A

19、.Littlechild,Gregory I.Giles,Fiona H.Fry,and Claus Jacob.Metal and Redox Modulation of Cysteine Protein Function.Chemistry&Biology 10(2003):677-693.lLuo,Chunling,Zhenguo Shen,Xiangdong Li,and Alan J.M.Baker.Enhanced Phytoextraction of Pb and Other Metals From Artificially Contaminated Soils Through

20、the Combined Application of EDTA and EDDS.Chemosphere 63(2006):1773-1784.lMachi,Lorena,Hisila Santacruz,Mario Sanchez,and Motomichi Inoue.Cd2+Sensiting Bichromophore:Excimer Emission From an EDTA-Methylnaphthalene Derivative.Inorganic Chemistry Communications 10(2007):547-550.lNayak,Manoj K.,Jangwon Seo,Sanghyuk Park,and Soo Young Park.Colorimetric and Highly Selective Turn-on Fluorescent Anion Chemosensors with Excited State Proton Transfer.Journal of Photochemistry and Photobiology(2007).ACKNOWLEDGEMENTS l Mr.Edward Irwinl Duncan Quarless,Ph.D.l Alicia Bowenl Dr.Sat Battacheryal HCS Staff