Reaction of carbon disulfide with nickel(i1)-amine complexes
|
|
- Hugh Kelley
- 6 years ago
- Views:
Transcription
1 Reaction of carbon disulfide with nickel(i1)-amine complexes B. JACK MCCORMICK AND ROY I. KAPLAN Department of Cl~emistry, West Virginia Ut~iversity, Morgantown, W. Ya Received January 27, 1970 Can. J. Chem. Downloaded from by on 04/06/18 The reaction of carbon disulfide with a variety of nickel(i1)-amine complexes has been carried out. It has been found that dithiocarbamate complexes are readily formed under the proper conditions, and the synthetic procedures presented provide a convenient and direct route to such compounds. Complexes having hydroxyl and mercaptide groups in addition to amine groups have been found to give exclusively dithiocarbamate complexes, rather than xanthates or trithiocarbonates. The infrared and optical spectra of the complexes have been measured and are discussed in terms of the proposed structures of the complexes. Canadian Journal of Chemistry, 48, 1876 (1970) Introduction While N,N-dialkyldithiocarbamate complexes of nickel(i1) and other transition metal ions have been known for many years (I), most of them have been prepared by metathetical reactions between a salt of a transition metal and that of a N,N-dialkyldithiocarbamic acid. Very recently there have been a few reports on the preparation of dithiocarbamate complexes by carbon disulfide insertion reactions, viz. Bradley and Gitlitz (2, 3) have made use of the carbon disulfide insertion reaction to prepare a number of interesting complexes of early transition metals. In a review (4) Lappert has summarized the results of studies concerned with the insertion of carbon disulfide into several types of metal-nitrogen bonds. In view of the possible synthetic utility of carbon disulfide insertion reactions, we have investigated the reaction of CS, with a variety of nickel(i1)-amine complexes involving: (I), a monodentate amine; (11), bidentate primary amines; (111), bidentate amines in which one donor nitrogen atom is in a pyridine ring; (IV), bidentate amines containing hydroxyl and mercaptide functional groups; and (V), a tridentate amine. Six of the complexes prepared have not been reported previously. Studies of selected properties of the complexes have been made, and the results are discussed in relation to the structures of the complexes. Experimental All of the amine complexes were prepared by known or modifications of known procedures (5). Dimethyl sulfoxide was distilled under nitrogen before use, and solution spectra were measured in Fisher "Spectroanalyzed" solvents. Reaction Procedures Several solvents for the insertion reactions were examined. Among these were water, methanol, ethanol, acetone, and N,N-dimethylformamide. While the reactions did proceed in these solvents, they were very slow, requiring 3 to 4 days. In many cases the slow rate of reaction undoubtedly was due to the lack of mutual solubility of the metal amine and carbon disulfide in the solvent. The most suitable solvent found was dimethyl sulfoxide (DMSO), in which most of the reactions were complete in 30 min. The reactions were done under an atmosphere of N,, and the reaction products were not exposed to air until they had been partially dried. In general, the reactions were carried out by dissolving and/or suspending 0.05 mole of the amine complex in 50 ml of DMSO, to which was added 0.5 mole of carbon disulfide dissolved in loml of DMSO. Typically the solutions underwent a series of color changes, and after 30 min, 250 ml of water was added to the reaction mixture, whereupon a precipitate formed immediately. The precipitate was separated by filtration, washed with 500 ml of warm water and 200 ml of methanol, dried in a stream of nitrogen, and then dried at 64' in vacuo over P4OI0. The yields were high in all cases except system Ia. The reaction with bis(2-mercaptoethylamine)nickel(ii) proceeded very slowly at room temperature owing to the insolubility of the complex in DMSO, and the above general procedure was modified in that the reaction was carried out in a sealed, heavy walled glass tube at 70". Under these conditions the reaction was complete in 6 h. The analytical sample was recrystallized from DMSO. Special procedures also were necessary for the reaction of dichloro(l,l,7,7-tetraethyldiethylenetriamine)ni~kel(ii) with carbon disulfide. In this reaction, 0.03 mole of the amine complex in 50 ml of absolute ethanol was treated with 0.03 mole of CS,. The solution quickly turned from a deep red to a bright green color. After 20 min a green precipitate was filtered off, washed with ethanol, and air dried. Recrystallization from absolute ethanol followed by drying over P4OlO provided an analytically pure sample. Given in Table 1 are the systems studied and the products formed from each system. The systems are
2 McCORMICK AND KAPLAN: REACTION OF CS2 AND Ni(I1)-AMINE COMPLEXES
3 1878 CANADIAN JOURNAL OF CHEMISTRY. VOL. 48, 1970 Can. J. Chem. Downloaded from by on 04/06/18 - TABLE 2 Analytical data for dithiocarbamate complexes Carbon Hydrogen Nitrogen Sulfur Nickel Product* Calcd. Found Calcd. Found Calcd. Found Calcd. Found Calcd. Found IIa IIb IIc IId IIIa IIIb IVa IVb Va *The product numbers correspond to the systems and reactions given in Table 1. designated by numbers which correspond to those given in the Introduction for the various types of amines. Elemental analyses for all of the compounds are given in Table 2. Carbon, hydrogen, nitrogen, and sulfur analyses were done by Galbraith Laboratories, Knoxville, Tenn., but the nickel analyses were done in our laboratory by conductometric titrations with EDTA (5). Measurements Infrared spectra were recorded with Beckman IR-8 and IR-12 spectrometers using the Nujol mull technique. Solution spectra were measured with a Cary Model 14 Spectrophotometer; diffuse reflectance spectra were measured with the same instrument and a Model 1411 reflectance attachment. The proton nuclear magnetic resonance (n.m.r.) spectrum was obtained with a Varian Model HA-60 Spectrometer using TMS as a reference. Spectral data are summarized in Table 3. Results and Discussion General Aspects of Reactions Reaction of carbon disulfide with amine complexes of nickel(i1) provides a direct and convenient route to nickel(i1) dithiocarbamate complexes. This technique also should be suitable for the preparation of complexes of other transition metals. In many cases it is synthetically advantageous to use the direct method rather than a metathetical reaction. since the latter procedure requires the preparation of a dithiocarbamate salt, which frequently is unstable or difficult to prepare and isolate. While the detailed mechanism is not known. two mechanistic aspects of the reactions deserve comment. First, there is some indication that DMSO serves as a reactant, as well as a solvent. In all cases the initial product from the reactions is soluble in DMSO, and the addition of water is required for the precipitation of the desired complex. However, in several cases the complex precipitated is not soluble in DMSO. This may indicate that the initial species formed is a mixed ligand complex involving coordinated DMSO as well as dithiocarbamate. The second point concerns the fate of the proton displaced from the amine during the course of the reaction. In systems Ia through IVa, the protons, no doubt, react with excess amine displaced during the reaction, viz. R = alkyl, hydrogen In the case of Ni(mea), and Ni(tedt)Cl,, basic sites are maintained on the coordinated dithiocarbamate which accommodate the displaced protons. Specific Reactions, Properties, and Structures la. The reaction of carbon disulfide with N~(NH,),'+ is, in principle, the most simple system studied, and it was established from infrared studies that Ni(S,CNH,), is formed. However, the product obtained was not pure. This finding is not surprising since dithiocarbamic acid, its salts, and complexes are not stable (1). IIa-IId. The four starting complexes in this group involve bidentate diamine ligands, and there are two conceivable types of reaction products. Reaction can occur at one amine group of a given ligand, with the released proton reacting with the remaining amine group to give a zwitterion, or both amine groups can react to give a bisdithiocarbamate. Ethylenediamine forms a monodithiocarbamate zwitterion in the absence of added base (6) and a bisdithiocarbamate in the presence of sodium hydroxide (7). In the four cases studied here, bisdithiocarbamate
4 McCORMICK AND KAPLAN: REACTION OF CS2 AND Ni(I0-AMINE COMPLEXES 1879 TABLE 3 Infrared and electronic spectral data* - Vm,, Compound V(C=N) Reflectance DMSOt IIa( = IIb) (127) 23.3sh 23.5(1320)sh (4520) (23000) IIc (126) 24.0sh 24.1(1530)sh (3590) (23200) IId (68) 22.6sh 23.3(1620)sh (5560) (28200) IIIa (85) (234) 23.4 sh 23.8 (1400) sh IIIb (113) (220) 24.4 sh 23.8 (1420) sh IVa sh 16.1 (68) 23.5(1390)sh I (3860) *Electronic data is in kilokaysers (kk); sh ~ndicates a shoulder. Infrared data is in cm-1.?extinction coefficients (1 mole-' cm-1) are given in parentheses. ligands are formed, and the resulting insoluble, green complexes are undoubtedly polymeric, as indicated in Table 1. If zwitterionic ligands were involved, the complexes should show a degree of solubility in water, as well as infrared frequencies characteristic of quaternary ammonium groups. Similar complexes prepared by metathetical reactions have been reported previously (8). The structures given in Table 1 are idealized in the sense that only chelating dithiocarbamate groups are shown. Bridging ligands may be important, but such detailed structural features cannot be ascertained at this time. Aside from their polymeric nature, the complexes appear to be very similar to the many nickel(i1) dithio- carbamates that have been previously studied. The complexes are diamagnetic and show a characteristic (9) C=N stretching frequency in the cm-i region. The electronic spectra, as given in Table 3, are identical to that reported previously by Jorgensen (10) for bis(n,n-diethyldithiocarbamato)nickel(ii), except that the band at ca. 21 kk is not resolved. IIIa,b. In these chelating diamines there is one amine group that can react with carbon disulfide and one ring nitrogen atom that is not expected to enter into reaction with carbon disulfide. It was of interest to determine whether the pyridine nitrogen atom would remain coordinated after the primary amine had undergone reaction with carbon disulfide. The results indicate that the pyridine moiety is displaced from the coordination sphere by the dithiocarbamate formed from the primary amine group to give the usual type of dithiocarbamate complex. In contrast to the polymeric complexes formed in system 11, these green, diamagnetic monomers are somewhat soluble in a variety of polar organic solvents. The magnitude of the C=N stretching frequency suggests that double bond character increases in the (S,)C-N bond (11) in going from system I1 to system 111. Electronic spectra measured at room temperature are identical to those that have been reported previously (10) for nickel(i1) dithiocarbamates. Since Coucouvanis and Fackler (11) have shown that certain nickel(i1) dithiocarbamates form adducts at low temperatures with nitrogenous bases, it was of interest to determine whether the present complexes enter into intra- or inter-molecular association with the uncoordinated pyridine groups. That such association can take place in solution with the concomitant formation of pseudo-octahedral nickel(i1) complexes was indicated by low temperature spectral studies. An acetone solution of system IIIb at room temperature exhibited the same absorption bands as those given in Table 3. As the solution was cooled to - 12", the color became lighter and a weak absorption band appeared at 10.2 kk. Further cooling to -80" resulted in a very pale green solution (no precipitation) with a moderately intense band at 10.2 kk. These spectral changes are in close agreement with those reported by Coucouvanis and Fackler (10) for bis(n,n-diethyldithiocarbamato)nickel(ii) in pyridine at temperatures from -80 to 20".
5 1880 CANADIAN JOURNAL OF CHEMISTRY. VOL. 48, 1970 IVa. Ethanolamine, HOCH2CH2NH2, reacts presence of a sulfhydryl group was provided by with carbon disulfide under room conditions to an n.m.r. study in DMSO-d,, where a resonance provide the dithiocarbamate rather than the due to the proton on the sulfur atom was located xanthate, HS2COCH2CH2NH2, which goes to at 6.60 T. 2-mercaptooxazoline on standing (12). Hence, it Va. The tedt complex reacted quite readily to was of interest to determine the course of reaction give a complex of a positively charged dithioof carbon disulfide with a coordinated amine carbamate ligand. This complex, prepared by an containing an -OH group. In principle, it is alternate route, has been discussed elsewhere (15). possible to form a dithiocarbamate, a xanthate, or a mixed dithiocarbamate-xanthate complex. This work was supported by the National Science ~h~ results indicate that reaction takes place Foundation through Grant NO. GP-6671 and through a grant that supported the purchase of the IR-12 Specexclusively at the nitrogen atoms to provide a trometer. polymeric complex having the structure shown in Table 1. The color, solubility, magnetic, and 1. G. D. THORN and R. A. LUDWIG. The dithioelectronic spectral properties of the complex were carbamates and related compounds. Elsevier Publ. essentially identical to those shown by the com- Co., New York D. C. BRADLEY and M. GITLITZ. Chem. plexes in Group 11. The CLN and OH stretching Commun. 289 (1965). frequencies were located at 1520 and 3375 cm-l, 3. D. C. BRADLEY and M. H. GITLITZ. J. Chem. Soc. A, 1152 (1969). and there were no bands in the 4. M. F. LAPPERT. Advances in organometallic cm-' region that could be attributed chemistry. Edited by F. G. A. Stone and R. West. Academic Press, Inc., New York. pp a 'anthate (I3)' The was 5. R. I. KAPLAN. Ph.D. Thesis, West Virginia Universtable and did not decompose to provide a sity, Morgantown, West Virginia mercaptooxazoline. 6. A. W. HOFMAN. Ber. 5, 240 (1872). 7' IVb. 2-Mercaptoethylamine is known to react A' Y. YAKUBoVICH and V. A. KLIMovA. J. Chem. U.S.S.R., 9, 1777 (1939). with carbon disulfide to give the trithiocarbonate 8. L. c. A. THOMPSON and R. O. MOYER. J. Inorg. zwitterion (14), but it was found in this work that Chem (1965). 9. J. CHATT, L. A. DUNCANSON, and L. M. VENANZI. coordinated mea reacts to give the dithiocar- Suomen Kem. B29, 75 (1956). bamate. Upon displacement from the coordina- 10. C. K. JORGENSEN. J. Inorg. Nucl. Chem. 24, 1571 (1962). sphere the mercapto becomes 11. D. COUCOUVANIS and J. P. FACKLER, JR. Inorg. protonated to provide a monomer of the type Chem. 6,2047 (1967). shown,in Table 1. This reaction represents a 12. P. G. SERGEEV and S. N. IVANOVA. J. Gen. Chem. U.S.S.R., 7, distinct example of the mediation of an organic 1495 (1937). 13. G. W. WATT and J. MCCORMICK. Spectrochim. reaction by a metal ion. Complex IVb is green, Acta, 21, 753 (1965). slightly soluble in polar organic solvents, and l4 ~ p fii, k ~ ~ ~ i and ~ J- MICKLES. ~ 6 diamagnetic. CzN and weak S-H 15. B. J. MCCORMICK, B. P. STORMER, and R. I. KAPLAN. stretching frequencies were found at 1502 and Inorg. Chem. 8, 2522 (1969) cm-', respectively. Further evidence for the
Mixed Ligand Complexes of Transition Metal Chelates of 1-nitroso-2-naphthol and 8-hydroxyquinoline with Picolinic Acid and Quinaldinic acid
ISSN: 0970-020 ; CDEN: JCHEG riental Journal of Chemistry 2011, Vol. 27, No. (1): Pg. 287-291 http://www.orientjchem.org Mixed igand Complexes of Transition Metal Chelates of 1-nitroso-2-naphthol and 8-hydroxyquinoline
More informationAlkali Metal Salts Of Some Organic Acids
ISSN (O) 2454-1362 Alkali Metal Salts Of Some Organic Acids Shahnawaz Mahmood Associate Professor and Head of the Department of Applied Sciences & Humanities Mewat Engineering College, Palla, Nuh, HARYANA
More informationExperiment 3. Condensation Reactions of Ketones and Aldehydes: The Aldol Condensation Reaction.
Experiment 3. Condensation Reactions of Ketones and Aldehydes: The Aldol Condensation Reaction. References: Brown & Foote, Chapters 16, 19, 23 INTRODUCTION: This experiment continues the saga of carbon-carbon
More informationTRANSITION METAL COMPLEXES OF BENZOYL ACETONE GLYCINE (L''H2)
TRANSITION METAL COMPLEXES OF BENZOYL ACETONE GLYCINE (L''H2) A.K. Mumthaz Structural, thermoanalytical and antitumour studies on some transition metal complexes of schiff bases Thesis. Department of Chemistry,
More informationNaming salts. Metal Acid Salt. Sodium hydroxide reacts with Hydrochloric acid to make Sodium chloride
Naming salts A salt is any compound formed by the neutralisation of an acid by a base. The name of a salt has two parts. The first part comes from the metal, metal oxide or metal carbonate. The second
More informationSynthesis of Schiff s Base Derivatives Using Water as Solvent.(A Green Methodology)
Synthesis of Schiff s Base Derivatives Using Water as Solvent.(A Green Methodology) Ajmal R. Bhat 1, M. Hussain Wagay 2 1,2 Department of Chemistry, Sant Baba Bhag Singh University, Jalandhar, Punjab 144030
More informationJournal of Chemical and Pharmaceutical Research
Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research ISSN No: 0975-7384 CODEN(USA): JCPRC5 J. Chem. Pharm. Res., 2011, 3(6):195-199 Synthesis and physico -chemical studies of
More informationElectronic Supporting Information for
Electronic Supporting Information for An efficient long fluorescence lifetime polymer-based sensor based on europium complex as chromophore for the specific detection of F -, CH 3 COO - -, and H 2 PO 4
More informationSYNTHESIS OF AN AZO DYE revisited (1 or 2 credits)
SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) This lab you can revisit the fist experiment of this quarter and synthesize more azo dyes of your choice. The old procedure is given below followed by
More informationPelagia Research Library
Available online at www.pelagiaresearchlibrary.com Der Chemica Sinica, 2015, 6(7):78-86 Synthesis and structural elucidation of Famciclovir B Sudha Rani 1, Ramana Kumar Kakarla 1 * and Srilalitha Vinnakota
More informationHonors Cup Synthetic Proposal
onors Cup Synthetic Proposal Section: 270-V Group Members: Azhar Carim, Ian Cross, Albert Tang Title: Synthesis of indigo from -(2-bromoethyl)-2-nitrobenzamide Introduction: Indigo has been used as a dye
More informationCr(III),Mn(II),Fe(III),Co(II),Ni(II),Cu(II) and Zn(II) Complexes with Diisobutyldithiocarbamato Ligand
ISSN: 0973-4945; CODEN ECJHAO E- Chemistry http://www.e-journals.net 2011, 8(4), 2020-2023 Cr(III),Mn(II),Fe(III),Co(II),Ni(II),Cu(II) and Zn(II) Complexes with Diisobutyldithiocarbamato Ligand MOHAMMAD
More informationSynthesis and Characterization of Dioxouranium (VI) complexes with Salicylyl hydrazine based Mixed Ligands
IOSR Journal of Engineering (IOSRJEN) ISSN (e): 22503021, ISSN (p): 22788719 Vol. 07, Issue 09 (September. 2017), V2 PP 5559 www.iosrjen.org Synthesis and Characterization of Dioxouranium (VI) complexes
More informationAnnals of West University of Timisoara
Annals of West University of Timisoara Series Chemistry 13 (1) (2004) 27-32 SYNTHESIS IN NON-AQUEOUS MEDIUM OF SOME SYMMETRICAL DISAZO DIRECT DYES DERIVED FROM 4,4 -DIAMINOSTILBENE-2,2 -DISULPHONIC ACID
More informationAppendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
More informationKinetic Isotope Effects
1 Experiment 31 Kinetic Isotope Effects Isotopic substitution is a useful technique for the probing of reaction mechanisms. The change of an isotope may affect the reaction rate in a number of ways, providing
More informationChapter 20 Amines-part 2
Reactions of Amines Lone pair on the nitrogen directs the chemistry of amines Chapter 20 Amines-part 2 The nitrogen lone pair can also make a carbon nucleophilic by resonance Amines can also activate carbons
More informationSynthesis and Structure of the Cadmium (II) Complex: [Cd(C 5 H 5 N) 2 (S 2 CO-n-C 4 H 9 ) 2 ]
Molecules 2002, 7, 549-553 molecules ISSN 1420-3049 http://www.mdpi.org Synthesis and Structure of the Cadmium (II) Complex: [Cd(C 5 H 5 N) 2 (S 2 CO-n-C 4 H 9 ) 2 ] Xu Hong Jiang 1,2, Wei Guang Zhang
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationSupporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor
Supporting information Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Toni Mäkelä, a Elina Kalenius a and Kari Rissanen a* a University of Jyvaskyla, Department of Chemistry, Nanoscience
More informationSYNTHESIS OF AN AZO DYE revisited (1 or 2 credits)
SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) This lab you can revisit the fist experiment of this quarter and synthesize more azo dyes of your choice. The old procedure is given below followed by
More informationPreparation and some properties of cyano complexes of the [M(CN) 5 L] 3 - type
Preparation and some properties of cyano complexes of the [M(CN) 5 L] 3 - type J. SKORŠEPA and K. GYORYOVÁ Department of Inorganic Chemistry, Faculty of Natural Science. P. J. Šafárik University, CS-04154
More informationElectronic Supplementary Information. Reversible, Solid State Capture of Carbon Dioxide by Hydroxylated Amidines. Myungsook Kim, and Ji-Woong Park*
Electronic Supplementary Information Reversible, Solid State Capture of Carbon Dioxide by Hydroxylated Amidines Myungsook Kim, and Ji-Woong Park* Department of Materials Science and Engineering, Gwangju
More informationSYNTHESIS AND IDENTIFICATION WATER-SOLUBLE TRIS-MALONATE OF LIGHT FULLERENE C 60 [= C(COOH) 2 ] 3
NANOSYSTEMS: PHYSICS, CHEMISTRY, MATHEMATICS, 2014, 5 (2), P. 315 319 SYNTHESIS AND IDENTIFICATION WATER-SOLUBLE TRIS-MALONATE OF LIGHT FULLERENE C 60 [= C(COOH) 2 ] 3 K. N. Semenov 1, N. A. Charykov 2,3,
More informationHigh-Performance Blend Membranes Composed of An Amphoteric Copolymer Containing Supramolecular Nanosieves for Direct Methanol Fuel Cells
Electonic Supplementary Information (ESI) for Chemical Communications High-Performance Blend Membranes Composed of An Amphoteric Copolymer Containing Supramolecular Nanosieves for Direct Methanol Fuel
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany A Distinctive Organocatalytic Approach to Complex Macromolecular Architectures Olivier Coulembier, Matthew 5. 5iesewetter, Andrew Mason, Philippe
More informationIodination of Salicylamide
Iodination of Salicylamide lectrophilic Aromatic Substitution Aromatic compounds are unusually stable because of the delocalization of their electrons. Given that the cloud is so stable, aromatic compounds
More informationmedia), except those of aluminum and calcium
1- Aspirin occurs as white crystals or as a white crystalline powder. 2- It is slightly soluble in water (1:300), soluble in alcohol (1 :5), chloroform (1:17) & ether (1:15). It dissolves easily in glycerin.
More informationEffect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationExperiment 2 Solvent-free Aldol Condensation between 3,4-dimethoxybenzaldehyde and 1-indanone
Experiment 2 Solvent-free Aldol Condensation between 3,4-dimethoxybenzaldehyde and 1-indanone Chemical Concepts Carbonyl chemistry, base catalyzed aldol reaction, melting point, recrystallization Green
More informationA series of Schiff's bases and secondary amine derivatives from
A series of Schiff's bases and secondary amine derivatives from W. KREMERS AND J. W. STEELE School of Pharmacy, University of Manitoba, Winnipeg, Manitoba Received November 8, 1966 Can. J. Chem. Downloaded
More informationOrganolithium Compounds *
OpenStax-CNX module: m32444 1 Organolithium Compounds * Andrew R. Barron This work is produced by OpenStax-CNX and licensed under the Creative Commons Attribution License 3.0 One of the major uses of lithium
More informationSupporting Information
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,
More information18. Arene Diazonium Ion Reactions
18. Arene Diazonium Ion Reactions A. Introduction In the previous laboratory experiment, you explored the functionalization of benzene via electrophilic aromatic substitution reactions. In these reactions,
More informationSimple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for: Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their
More informationChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
More informationSupporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer
Supporting Information for Polybenzimidazolium Salts: A ew Class of Anion-Conducting Polymer Owen D. Thomas, Kristen J. W. Y. Soo, Timothy J. Peckham, Mahesh P. Kulkarni and Steven Holdcroft* Department
More informationDrastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril
SUPPORTING INFORMATION Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril Lidia Strimbu Berbeci, Wei Wang and Angel E. Kaifer* Center for Supramolecular Science and
More informationCyanide, colorimetric, pyridine-pyrazolone
Cyanide, colorimetric, pyridine-pyrazolone Parameters and Codes: Cyanide, dissolved, I-1300-85 mg/l as CN): 00723 Cyanide, total, I-3300-85 (mgll as CN): 00720 Cyanide, total-in-bottom-material, dry wt,
More informationExperiment 17 Preparation of Methyl Orange
Experiment 17 Preparation of Methyl range In this experiment you will prepare methyl orange, an azo dye that forms beautiful orange crystals and is used as an acid-base indicator (Figure 17.1). The anion
More informationEmpirical formula C 4 H 6 O
AP Chem Test- Titration and Gravimetric Analysis p. 2 Name date 4. Empirical Formula A compound is analyzed and found to contain 68.54% carbon, 8.63% hydrogen, and 22.83% oxygen. The molecular weight of
More informationSupporting Information
Supporting Information German Edition: DOI: High Catalytic Activity of Heteropolynuclear Cyanide Complexes Containing Cobalt and Platinum Ions: Visible-Light Driven Water Oxidation** Yusuke Yamada,* Kohei
More information18 Macroscale and Microscale Organic Experiments
360465-P01[01-024] 10/17/02 16:16 Page 18 Sahuja Ahuja_QXP_03:Desktop Folder:17/10/02: 18 Macroscale and Microscale Organic Experiments Preparing a Laboratory Record Use the following steps to prepare
More informationSupporting Information
Supporting Information Highly Selective Colorimetric Chemosensor for Co 2+ Debabrata Maity and T. Govindaraju* Bioorganic Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced
More informationSynthesis and spectroscopic investigations of complexes of lanthanide nitrates with 5-nitroisoquinoline-2-oxide
Proc. Indian Acad. Sci. (Chem. Sci.), Vol. 99, No. 3, September 1987, pp. 137-141. 9 Printed in India. Synthesis and spectroscopic investigations of complexes of lanthanide nitrates with 5-nitroisoquinoline-2-oxide
More informationCHEM 3760 Orgo I, F14 (Lab #11) (TECH 710)
CHEM 3760 Orgo I, F14 (Lab #11) (TECH 710) Identification of an Unknown by IR PRELAB (PreLab is due before entering the lab.) Every student has to prepare for each experiment by answering the Pre-Laboratory
More informationNaBr, H2SO4 CH3CH2CH2CH2Br + NaHSO4 + H2O. 1-Bromobutane bp C den MW n 1.439
Exp t 140 The SN2 Reaction: 1-Bromobutane from K. L. Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston. p247; revised 2/22/02 Prelab Exercise: Review the
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Carbene Activation of P 4 and Subsequent Derivatization Jason D. Masuda, Wolfgang W. Schoeller, Bruno Donnadieu, and Guy Bertrand * [*] Dr.
More informationEXPERIMENT: LIMITING REAGENT. NOTE: Students should have moles of reactants in DATASHEET converted into masses in grams prior to the lab period.
Revised 12/2015 EXPERIMENT: LIMITING REAGENT Chem 1104 Lab NOTE: Students should have moles of reactants in DATASHEET converted into masses in grams prior to the lab period. INTRODUCTION Limiting reactant
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationBiasing hydrogen bond donating host systems towards chemical
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Biasing hydrogen bond donating host systems towards chemical warfare agent
More informationRule 2. Rule 1. Rule 4. Rule 3. Rule 5. Rule 6. Rule 7. Rule 8
Rule 1 Follow the directions in your course reader, of your teaching assistant and of your instructor. They are usually much more experienced doing chemistry. Rule 3 When in doubt, ask. This will make
More informationStudies on Coordination Behaviour of a Polydentate Schiff Base in Presence of Dimethyl Sulphoxide on Rare Earth Metal Ions
Studies on Coordination Behaviour of a Polydentate Schiff Base in Presence of Dimethyl Sulphoxide on Rare Earth Metal Ions Jisha. M. J 1, G. Rajendran 2 1 Department of Chemistry, Christian College Kattakada,
More informationElectronic supporting information for
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic supporting information for The effects of an ionic liquid on
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supporting Information A fast and selective probe for detection of CN - and F -
More informationSYNTHESIS AND CHARACTERIZATION OF SOME TETRADENTATE SCHIFF BASE COMPLEXES
Int. J. Chem. Sci.: 6(4), 2008, 1991-1999 SYNTHESIS AND CHARACTERIZATION OF SOME TETRADENTATE SCHIFF BASE COMPLEXES VASISHTA D. BHATT, KETUL N. PATEL, NILESH H. PATEL a and JIGNESH P. RAVAL a Dept. of
More informationGRAVIMETRIC ANALYSIS OF A CHLORIDE SALT. REFERENCES: Nelson, J., Chemistry: The Central Science, 3 rd edition, Prentice-Hall, 1985
1 GRAVIMETRIC ANALYSIS OF A CHLORIDE SALT REFERENCES: Nelson, J., Chemistry: The Central Science, 3 rd edition, Prentice-Hall, 1985 Typical techniques used in gravimetric analyses by quantitatively determining
More informationJohn H. MacMillan and Stephen S. Washburne. Dept of Chemistry, Temple University, Philadelphia, Pa 19122
Further Studies of the Interaction of Carbonyl Compounds with Organometallic Azides, the Reaction of Napthoquinones with Trimethylsilyl Azide John H. MacMillan and Stephen S. Washburne Dept of Chemistry,
More informationMercury(ll) cyanide complexes with some bidentate ligands
Proc. Indian Acad. Sci. (Chem. Sci.), Vol. 93, No. 8, December 1984, pp. 1265-1271. Printed in India. Mercury(ll) cyanide complexes with some bidentate ligands I S AHUJA Chemistry Department, Banaras Hindu
More informationE4 Acids, Bases, and Salts
E4 Acids, Bases, and Salts Session One of two session lab Complete Parts 1 and 2 in lab. If time allows, start or complete Part 3. Acids and Bases Q. Are acid-base properties of substances predictable
More informationA long-lived iridium(iii) chemosensor for the real-time
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2017 Supporting Information A long-lived iridium(iii) chemosensor for the real-time
More informationEXPERIMENT NINE Part I - The Standardization of Thiosulfate Solutions
EXPERIMENT NINE Part I - The Standardization of Thiosulfate Solutions In general, thiosulfate solutions are standardized by indirect methods, Primary-standard oxidizing agents such as KIO 3, As 2 O 3,
More informationph = - log [H3O+] Example: ph 7 = - log [ 1 x 10-7] [H3O+] = mole/liter units ph values are unitless
E4 Acids, Bases, and Salts Oct. 1517 and Oct. 2728* Session One of two session lab Complete Parts 1 and 2 in lab. Part 1. Structure and AcidBase Properties Q. Are properties of a compound predictable from
More informationReactions of cis-[pt(s~lfoxide)~cl~] with silver salts and synthesis of hydroxo-bridged platinum(i1) complexes with sulfoxides
Reactions of cis-[pt(s~lfoxide)~cl~] with silver salts and synthesis of hydroxo-bridged platinum(i1) complexes with sulfoxides FERNANDE D. ROCHON, PI-CHANG KONG, AND LOUISE GIRARD Dkpartement de chimie,
More informationSupplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni
Supplementary Figure 1 IR Spectroscopy. IR spectra of 1Cu and 1Ni as well as of the starting compounds, recorded as KBr-pellets on a Bruker Alpha FTIR spectrometer. Supplementary Figure 2 UV/Vis Spectroscopy.
More informationEpichlorohydrin coupling reactions with wood
Wood Science and Technology 28 (1994) 371-376 Springer-Verlag 1994 Epichlorohydrin coupling reactions with wood Part 1. Reaction with biologicallyactive alcohols R. M. Rowell, G. C. Chen Summary Properties
More informationSupplementary Material:
Supplementary Material: Water soluble amphiphilic gold nanoparticles with structured ligand shells Oktay Uzun, Ying Hu, Ayush Verma, Suelin Chen, Andrea Centrone, and Francesco Stellacci* Department of
More informationOne polymer for all: Benzotriazole Containing Donor-Acceptor Type Polymer as a Multi-Purpose Material
One polymer for all: Benzotriazole Containing Donor-Acceptor Type Polymer as a Multi-Purpose Material Abidin Balan a, Derya Baran a, Gorkem Gunbas a,b, Asuman Durmus a,b, Funda Ozyurt a and Levent Toppare
More informationElectronic Supplementary Information
Electronic Supplementary Information Simultaneous Production of p-tolualdehyde and Hydrogen Peroxide in Photocatalytic Oxygenation of p-xylene and Reduction of Oxygen with 9-Mesityl-1-Methylacridinium
More informationDepartment of Chemistry SUNY/Oneonta. Chem Organic Chemistry I
Department of Chemistry SUNY/Oneonta Chem 221 - Organic Chemistry I Examination #4 - ANSWERS - December 11, 2000 Answer to question #32 corrected 12/13/00, 8:30pm. INSTRUCTIONS This examination is in multiple
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 ROS-mediated Carbon Monoxide and Drug Release from Drug-conjugated Carboxyboranes Theppawut
More informationSynthesis and Spectral Studies of Cobalt (II) and Nickel (II) Complexes with 18-membered Macrocyclic Ligand Derived from Malonodihydrazide
ISSN: 0970-020 X; CODEN: OJCHEG Oriental Journal of Chemistry 2011, Vol. 27, No. (1): Pg. 277-281 http://www.orientjchem.org Synthesis and Spectral Studies of Cobalt (II) and Nickel (II) Complexes with
More informationSupplementary Information. Solvent-Dependent Conductance Decay Constants in Single Cluster. Junctions
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supplementary Information Solvent-Dependent Conductance Decay Constants in Single Cluster
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More informationThe Synthesis of Triphenylmethano. will synthesize Triphenylmethanol, a white crystalline aromatic
HEM 333L rganic hemistry Laboratory Revision 2.0 The Synthesis of Triphenylmethano ol In this laboratory exercise we will synthesize Triphenylmethanol, a white crystalline aromatic compound. Triphenylmethanol
More informationAldol Condensation Notes
Reminder: These notes are meant to supplement, not replace, the laboratory manual. Aldol Condensation Notes History and Application Condensation reactions are molecular transformations that join together
More informationCHAPTER 8 ISOLATION AND CHARACTERIZATION OF PHYTOCONSTITUENTS BY COLUMN CHROMATOGRAPHY
146 CHAPTER 8 ISLATIN AND CHARACTERIZATIN F PHYTCNSTITUENTS BY CLUMN CHRMATGRAPHY 8.1 INTRDUCTIN Column chromatography is an isolation technique in which the phytoconstituents are being eluted by adsorption.
More informationSYNTHESIS OF 15 N-LABELED ISOMERS OF 5-NITRO-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE (NTO)
SYNTHESIS OF 15 N-LABELED ISOMERS OF 5-NITRO-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE (NTO) Jimmie C. Oxley, James L. Smith, Kirk E. Yeager Chemistry Department New Mexico Institute of Mining & Technology Socorro,
More informationExperiment DE: Part II Fisher Esterification and Identification of an Unknown Alcohol
Experiment DE: Part II Fisher Esterification and Identification of an Unknown Alcohol Fisher Esterification of an Alcohol (Fraction A) On the Chem 113A website, under "Techniques" and "Videos" review the
More informationSupporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS
More informationInfluence of photo-isomerisation on host-guest interaction in poly(azocalix[4]arene)s
Electronic Supplementary Information Influence of photo-isomerisation on host-guest interaction in poly(azocalix[4]arene)s Szymon Wiktorowicz, Heikki Tenhu and Vladimir Aseyev *, Department of Chemistry,
More informationSupplementary Material
10.1071/CH17506_AC CSIRO 2018 Australian Journal of Chemistry 2018, 71(5), 341-347 Supplementary Material Magnesium alkoxide complexes of (benzimidazolylmethyl)amino ligands: Synthesis and applications
More informationThe FT-IR, FT-Raman, 1 Hand 13 CNMR study on molecular structure of sodium(i), calcium(ii), lanthanum(iii) and thorium(iv) cinnamates
Spectroscopy 24 (2010) 277 281 277 DOI 10.3233/SPE-2010-0442 IOS Press The FT-IR, FT-Raman, 1 Hand 13 CNMR study on molecular structure of sodium(i), calcium(ii), lanthanum(iii) and thorium(iv) cinnamates
More informationSupporting Information
Supporting Information A Diiron Amido-Imido Complex [(Cp*Fe) 2 (µ 2 -NHPh)(µ 2 -NPh)]: Synthesis and a Net Hydrogen Atom Abstraction Reaction to Form a Bis(imido) Complex Shin Takemoto, Shin-ichiro Ogura,
More informationTetrathiafulvalene radical cation (TTF +. ) Charge Transfer aggregates included in PMMA matrix, a Resonance Raman Study
Tetrathiafulvalene radical cation (TTF +. ) Charge Transfer aggregates included in PMMA matrix, a Resonance Raman Study B. F. Scremin 1 1-IOM CNR, Institute Officina dei Materiali of the National Research
More informationExp t 111 Structure Determination of a Natural Product
Exp t 111 Adapted by R. Minard, K. Smereczniak and Jon Landis (Penn State Univ.) from a microscale procedure used by the University of California, Irvine, in its undergraduate labs. The procedure is based
More informationAmines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature
Amines Reading: Wade chapter 19, sections 19-1-19-19 Study Problems: 19-37, 19-39, 19-40, 19-41, 19-44, 19-46, 19-47, 19-48, 19-51, 19-54 Key Concepts and Skills: Explain how the basicity of amines varies
More informationSupporting Information
Supporting Information An L-proline Functionalized Metallo-organic Triangle as Size-Selective Homogeneous Catalyst for Asymmertry Catalyzing Aldol Reactions Xiao Wu, Cheng He, Xiang Wu, Siyi Qu and Chunying
More informationAn improved preparation of isatins from indoles
An improved preparation of isatins from indoles Jiro Tatsugi,* Tong Zhiwei, and Yasuji Izawa Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, Yachigusa, Yakusa-cho,
More informationSYNTHESIS OF 1-BROMOBUTANE Experimental procedure at macroscale (adapted from Williamson, Minard & Masters 1 )
SYNTHESIS OF 1-BROMOBUTANE Experimental procedure at macroscale (adapted from Williamson, Minard & Masters 1 ) Introduction 1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced
More informationFigure S1 - Enzymatic titration of HNE and GS-HNE.
Figure S1 - Enzymatic titration of HNE and GS-HNE. Solutions of HNE and GS-HNE were titrated through their reduction to the corresponding alchools catalyzed by AR, monitoring the decrease in absorbance
More informationSynthesis of Tethered Chromium Carbene Complexes
SYNTHESIS OF TETHERED CHROMIUM CARBENE COMPLEXES 375 Synthesis of Tethered Chromium Carbene Complexes Nicole S. Lueck Faculty Sponsor: Curtis Czerwinski, Department of Chemistry ABSTRACT Hydroxycarbene
More informationElectronic Supplementary Information. Noninvasive Functionalization of Polymers of Intrinsic Microporosity for Enhanced CO 2 Capture
Electronic Supplementary Information Noninvasive Functionalization of Polymers of Intrinsic Microporosity for Enhanced CO 2 Capture Hasmukh A. Patel and Cafer T. Yavuz* Oxide and Organic Nanomaterials
More informationReversible uptake of HgCl 2 in a porous coordination polymer based on the dual functions of carboxylate and thioether
Supplementary Information Reversible uptake of HgCl 2 in a porous coordination polymer based on the dual functions of carboxylate and thioether Xiao-Ping Zhou, a Zhengtao Xu,*,a Matthias Zeller, b Allen
More informationSUPPLEMENTARY INFORMATION
SUPPLEMENTARY INFORMATION Supporting Information Kinetic Resolution of Constitutional Isomers Controlled by Selective Protection inside a Supramolecular Nanocapsule Simin Liu, Haiying Gan, Andrew T. Hermann,
More informationE4 Acids, Bases, and Salts
E4 Acids, Bases, and Salts Session One of two session lab Complete Parts 1 and 2 in lab. If time allows, start or complete Part 3. Reminder: Pre-lab report, page 112, due at start of lab. Acids and Bases
More informationCHAPTER 3. FABRICATION TECHNOLOGIES OF CdSe/ZnS / Au NANOPARTICLES AND NANODEVICES. 3.1 THE SYNTHESIS OF Citrate-Capped Au NANOPARTICLES
CHAPTER 3 FABRICATION TECHNOLOGIES OF CdSe/ZnS / Au NANOPARTICLES AND NANODEVICES 3.1 THE SYNTHESIS OF Citrate-Capped Au NANOPARTICLES Au NPs with ~ 15 nm were prepared by citrate reduction of HAuCl 4
More informationMonooxygenation of an appended phenol in a model system of tyrosinase: Implications on the enzymatic reaction mechanism*
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Supporting Information for Monooxygenation of an appended phenol in a model system of
More informationN-benzoyl glycine, 3-aminoacetophenone, 4-dimethylaminobenzaldehyde, potassium hydroxide, potassium nitrate and metal salts, MCl 2.
61 CAPTER 2. EXPERIMETAL 2.1. Materials -benzoyl glycine, 3-aminoacetophenone, 4-dimethylaminobenzaldehyde, potassium hydroxide, potassium nitrate and metal salts, MCl 2.n 2 (M = i, Cu and Cd) were purchased
More informationChemistry 283g- Experiment 4
EXPEIMENT 4: Alkenes: Preparations and eactions elevant sections in the text: Fox & Whitesell, 3 rd Ed. Elimination eactions of Alcohols: pg. 426-428, 431-432 Electrophilic Addition to Alkenes: pg. 484-488,
More information