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Journal Articles: 42 results
Experimental Design and Optimization: Application to a Grignard Reaction  Naoual Bouzidi and Christel Gozzi
This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.
Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ. 2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
Synthesis
A Three-Step Laboratory Sequence To Prepare a Carbene Complex of Silver(I) Chloride  John P. Canal, Taramatee Ramnial, Lisa D. Langlois, Colin D. Abernethy, and Jason A. C. Clyburne
Presents a multistep inorganic synthesisof N-heterocyclic carbenes that introduces students to modern organometallic chemistry, multinuclear NMR (1H and 13C) spectroscopy, and novel coordination geometries and valence states of carbon.
Canal, John P.; Ramnial, Taramatee; Langlois, Lisa D.; Abernethy, Colin D.; Clyburne, Jason A. C. J. Chem. Educ. 2008, 85, 416.
Coordination Compounds |
NMR Spectroscopy |
Organometallics |
Synthesis
Acylation of Ferrocene: A Greener Approach  Kurt R. Birdwhistell, Andy Nguyen, Eric J. Ramos, and Robert Kobelja
This article describes an acylation of ferrocene that is more eco-friendly than the conventional experiment, which has been modified by replacing mineral acid with a polymeric acid catalyst and using microwave instead of conventional heating.
Birdwhistell, Kurt R.; Nguyen, Andy; Ramos, Eric J.; Kobelja, Robert. J. Chem. Educ. 2008, 85, 261.
Catalysis |
Chromatography |
Green Chemistry |
Organometallics |
Synthesis |
Transition Elements |
Brønsted-Lowry Acids / Bases
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment  Michael A. G. Berg and Roy D. Pointer
Describes the use of a commercially available Grignard reagent in a Grignard synthesis that avoided the failures typically associated with the Grignard reaction.
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007, 84, 483.
Aldehydes / Ketones |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics |
Synthesis
A Research-Based Laboratory Course in Organic Chemistry  Thomas A. Newton, Henry J. Tracy, and Caryn Prudenté
Describes the development, implementation, evolution, and evaluation of a unique approach to laboratory instruction in organic chemistry. The new course involves a combinatorial strategy that offers every student a different group of 14 metallole as their personal synthetic target.
Newton, Thomas A.; Tracy, Henry J.; Prudenté, Caryn. J. Chem. Educ. 2006, 83, 1844.
Combinatorial Chemistry |
Organometallics |
Synthesis |
Undergraduate Research
The Amazingly Versatile Titanocene Derivatives  Donald C. Bowman
Derivatives of titanocene are remarkably versatile in their chemical applications. This article presents a brief review of the derivatives' uses in the fields of polymers, medical oncology, and organic synthesis.
Bowman, Donald C. J. Chem. Educ. 2006, 83, 735.
Applications of Chemistry |
Catalysis |
Drugs / Pharmaceuticals |
Organometallics |
Polymerization |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry Laboratory  Olivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. Dalke
A microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected.
Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ. 2005, 82, 1059.
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Organometallics |
Reactive Intermediates |
Synthesis
Preparation and Investigation of Monodentate and Bridging Pyrazole Complexes  Wynne Evans
This practical exercise describes the preparation and characterization of h1-coordinated pyrazole and 3,5-dimethylpyrazole nickel species and the investigation of their reactions with triethylamine. The latter reaction provides a route to preparing a polymer with bridging pyrazolato ligands, coordinating in an exobidentate (N, N?) fashion. We use this experiment, with undergraduate chemistry students, as part of a course providing an introduction to coordination chemistry. The exercise could be extended to take the form of an individual or class project. Suggestions for variations on the described experiment are included.
Evans, Wynne. J. Chem. Educ. 2004, 81, 1191.
Coordination Compounds |
Synthesis |
IR Spectroscopy |
Magnetic Properties |
Organometallics |
Titration / Volumetric Analysis |
Transition Elements |
UV-Vis Spectroscopy |
Spectroscopy |
Crystal Field / Ligand Field Theory
Boron Clusters Come of Age  Russell N. Grimes
This article attempts to summarize the current state of the art, illustrated by examples selected to convey some of the excitement and possibilities for future exploitation of these remarkable compounds.
Grimes, Russell N. J. Chem. Educ. 2004, 81, 657.
Main-Group Elements |
Materials Science |
Organometallics
Synthesis, Kinetics, and Thermodynamics: An Advanced Laboratory Investigation of the Cis–Trans Isomerization of Mo(CO)4(PR3)2   Ashfaq A. Bengali and Kim E. Mooney
The students synthesize the cis complex and then study its conversion to the trans isomer. This experiment illustrates the important relationship between kinetics and thermodynamics and the results emphasize the selfconsistency of the data.
Bengali, Ashfaq A.; Mooney, Kim E. J. Chem. Educ. 2003, 80, 1044.
Kinetics |
Metals |
Organometallics |
Thermodynamics |
Stereochemistry |
Synthesis |
Coordination Compounds
Network Complexes of Copper(I) Halides  Robert D. Pike, Peter M. Graham, Kathryn A. Guy, T. Jason Johnson, Jenine R. Cole, Sarah M. Stamps, and Lauren E. Klemmer
Procedure to introduce self-assembled metal-organic coordination networks.
Pike, Robert D.; Graham, Peter M.; Guy, Kathryn A.; Johnson, T. Jason; Cole, Jenine R.; Stamps, Sarah M.; Klemmer, Lauren E. J. Chem. Educ. 2001, 78, 1522.
Coordination Compounds |
Equilibrium |
Nanotechnology |
Stoichiometry |
Organometallics
Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory  John Hanson
Laboratory series to introduce students to an important synthetic method and many common techniques used in running reactions, purifying products, and characterizing compounds.
Hanson, John. J. Chem. Educ. 2001, 78, 1266.
Catalysis |
Chirality / Optical Activity |
Synthesis |
Organometallics |
Stereochemistry |
Epoxides |
Enantiomers |
Aromatic Compounds
Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory  Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (h6-Anisole)Cr(CO)3 Complex  Ashfaq A. Bengali, Cindy Samet, and Samantha B. Charlton
A laboratory activity that integrates fundamental concepts of organic and organometallic chemistry and then employs standard instrumental techniques (GC) and molecular modeling to justify the results.
Bengali, Ashfaq A.; Samet, Cindy; Charlton, Samantha B. J. Chem. Educ. 2001, 78, 68.
Aromatic Compounds |
Synthesis |
Organometallics |
Gas Chromatography |
Molecular Modeling
A Phthalocyanine Synthesis Group Project for General Chemistry  Darren K. MacFarland, Christopher M. Hardin, and Michael J. Lowe
A group experiment synthesizing phthalocyanine dyes in one step from commercially available starting materials is described. The importance of a metal template is explored. The experiment is suitable for a second-semester general chemistry course.
MacFarland, Darren K.; Hardin, Christopher M.; Lowe, Michael J. J. Chem. Educ. 2000, 77, 1484.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
Visible Aromatic Electronic Effects Using a Series of Substituted Copper Phthalocyanines  Darren K. MacFarland, Solomon Lieb, and Jessica Oswald
Phthalocyanines provide an opportunity to directly observe electronic effects in an aromatic system through color changes that are dependent on the nature of peripheral substituents. Simple, reliable syntheses of electron-poor and electron-rich phthalocyanines are reported, along with corresponding UV-visible spectra.
MacFarland, Darren K.; Lieb, Solomon; Oswald, Jessica. J. Chem. Educ. 2000, 77, 1482.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity  Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
Synthesis and Structure-Property Relationships in (h6-Arene)Cr(CO)3 Chemistry: From Guided Experiments to Discovery Research  Allen D. Hunter, Larry J. Bianconi, Steven J. DiMuzio, and Dianne L. Braho
Since instructors can have each student prepare a different complex, they are ideal targets for student directed "discovery research" lab projects. Teams of students can compare how their syntheses and the physical, spectroscopic, and electrochemical properties of their products vary as a function of the arenes' structures.
Hunter, Allen D.; Bianconi, Larry J.; DiMuzio, Steven J.; Braho, Dianne L. J. Chem. Educ. 1998, 75, 891.
Microscale Lab |
Organometallics |
IR Spectroscopy |
NMR Spectroscopy |
Electrochemistry |
Synthesis |
Coordination Compounds
The Microscale Synthesis and Electrochemistry of Low-Valent Mononuclear Complexes (?3-C3H5)Fe(CO)3 X (X = I, Br, Cl)  Enrico Mocellin, Richard Russell, and Mauro Ravera
By combining experimental procedures which place microscale, chemical synthesis, and an inclusive, unified, product characterization in perspective, we have afforded the student the scope to obtain progressive, disciplined results and the opportunity to discuss these in the subsequent reporting.
Mocellin, Enrico; Russell, Richard; Ravera, Mauro. J. Chem. Educ. 1998, 75, 773.
Organometallics |
Microscale Lab |
Electrochemistry |
Synthesis
Synthesis of 4-Nitro-1-Pentynylbenzene: An Example of Transitional Metal-Mediated Cross-Coupling  Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Synthesis of the target compound exemplifies contemporary Pd-mediated cross-coupling methodologies. In this regard, several fundamental mechanistic aspects of catalytic organometallic chemistry are illustrated, including oxidative addition, transmetallation, and reductive elimination.
Brisbois, Ronald G. ; Batterman, William G.; Kragerud, Scott R. J. Chem. Educ. 1997, 74, 832.
Synthesis |
Microscale Lab |
Organometallics |
Transition Elements |
Aromatic Compounds
An Advanced Inorganic Laboratory Experiment Using Synthesis and Reactivity of a Cycloheptatriene Molybdenum Complex  Timmers, Francis J.; Wacholtz, William F.
The reactions in the laboratory experiment described herein involve the synthesis, reactivity, and characterization of cycloheptatriene molybdenum.
Timmers, Francis J.; Wacholtz, William F. J. Chem. Educ. 1994, 71, 987.
Synthesis |
Organometallics |
Alkenes
Cobalt Cluster Chemistry  Humphrey, Mark G.; Rowbottom, Colleen A.
The authors present an experiment illustrating some diverse principles of metal cluster chemistry, employing the relatively cheap metal cobalt.
Humphrey, Mark G.; Rowbottom, Colleen A. J. Chem. Educ. 1994, 71, 985.
Organometallics
Synthesis and Characterization of [Ag{CH(PPh3)C(O)CH3)}2]NO3: A Multitechnique Experiment in Organometallic Chemistry  Vicente, Jose; Chicote, Maria Teresa; Saura-Llamas, Isabel
The proposal for this technique highlights advantages such as using starting materials that are air-stable and several instrumental techniques can be employed to gain information about the products.
Vicente, Jose; Chicote, Maria Teresa; Saura-Llamas, Isabel J. Chem. Educ. 1993, 70, 163.
Organometallics |
Spectroscopy
Organometallic chemistry: A course designed for sophomore chemistry students  Miessler, Gary L.; Spessard, Gary O.
Descriptin of a new course offered during the one-month January interim session for students who have completed one semester of organic chemistry. This paper describes the course so that it may be adapted at other institutions. Students have responded favorably to this course.
Miessler, Gary L.; Spessard, Gary O. J. Chem. Educ. 1991, 68, 16.
Organometallics
Cobaloximes as vehicles for college teaching  Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D.
Cobaloximes are probably the most accessible and "least nasty" of all organometallic compounds, are highly colored, exhibit unusual oxidation states, demonstrate a vivid nucleophilic attack, and lend themselves to chromatographic investigation without the need for UV light.
Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D. J. Chem. Educ. 1990, 67, 973.
Coordination Compounds |
Organometallics |
Nucleophilic Substitution
The systematic study of the organotransition metal compounds  Carriedo, Gabino A.
This article describes an extension to classifying organometallic complexes according to the carbon-donor ligand, that may be useful to show how the various existing types of low-valence organotransition metal complexes can be constructed.
Carriedo, Gabino A. J. Chem. Educ. 1990, 67, 294.
Organometallics |
Crystal Field / Ligand Field Theory
Synthesis and reactivity of ?5-cyclopentadienylruthenium compounds: An organometallic chemistry experiment  Ballester, L.; Gutierrez, A.; Perpinan, M. F.
Procedure permits the application of concepts regarding the reactivity of organometallic compounds and the use of IR and NMR spectral data in the characterization of the synthesized complexes.
Ballester, L.; Gutierrez, A.; Perpinan, M. F. J. Chem. Educ. 1989, 66, 777.
Organometallics |
IR Spectroscopy |
NMR Spectroscopy |
Coordination Compounds
The early history of organotin chemistry  Nicholson, John W.
Survey of the first 35 years of organotin chemistry.
Nicholson, John W. J. Chem. Educ. 1989, 66, 621.
Organometallics
Oxidation numbers and their limitations  Woolf, A. A.
An in-depth look at oxidation numbers of various elements in a number of different compounds.
Woolf, A. A. J. Chem. Educ. 1988, 65, 45.
Organometallics |
Oxidation State |
Oxidation / Reduction
An undergraduate experiment in homogeneous catalysis: Synthesis of phenylethoxycarbene tungsten pentacarbonyl and polymerization of norbornene and phenylacetylene  Villemin, Dider
An experiment to illustrate the chemistry of metal carbenes.
Villemin, Dider J. Chem. Educ. 1987, 64, 183.
Synthesis |
Organometallics |
Catalysis
Some aspects of the bioinorganic chemistry of molybdenum  Swedo, Kathleen Bizot; Enemark, John H.
The biological role of molybdenum, biophysical studies of the molybdenum atoms in molybdo-enzymes, and aspects of coordination chemistry that bear on the understanding of molybdo-enzymes.
Swedo, Kathleen Bizot; Enemark, John H. J. Chem. Educ. 1979, 56, 70.
Bioinorganic Chemistry |
Organometallics |
Enzymes |
Coordination Compounds |
Transition Elements
Phase transfer catalysis. Part II: Synthetic applications  Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
Biochemical roles of some essential metal ions  J. Chem. Educ. Staff
Summarizes the important biochemical roles played by ions of sodium, potassium, calcium, magnesium, zinc, iron, cobalt, and copper.
J. Chem. Educ. Staff J. Chem. Educ. 1977, 54, 761.
Metals |
Organometallics |
Bioinorganic Chemistry
One-credit hour undergraduate inorganic laboratory course  Burke, B. A.; Davenport, D. A.; Smith, T. J.; Walton, R. A.
Course structure and and outline of experiments.
Burke, B. A.; Davenport, D. A.; Smith, T. J.; Walton, R. A. J. Chem. Educ. 1977, 54, 360.
Metals |
Transition Elements |
Synthesis |
Oxidation State |
Organometallics |
Coordination Compounds
The design of integrated inorganic experiments. An example from organo-transition-element chemistry  Hunt, G. R. A.
This lab was designed in response to a need for an integrated exercise in undergraduate practical chemistry.
Hunt, G. R. A. J. Chem. Educ. 1976, 53, 53.
Descriptive Chemistry |
NMR Spectroscopy |
Organometallics |
Transition Elements
Historical origins of organometallic chemistry. Part II, Edward Frankland and diethylzinc  Thayer, John S.
Considers Edward Frankland and his preparation of diethylzinc.
Thayer, John S. J. Chem. Educ. 1969, 46, 764.
Organometallics |
Synthesis
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
One hundred years of organosilicon chemistry  Muller, Richard
Summarizes the history organosilicon chemistry to commemorate the early contributions of Charles Friedel and James Mason Crafts.
Muller, Richard J. Chem. Educ. 1965, 42, 41.
Organometallics
Organometallic derivatives of the transition elements  Kaesz, Herbert D.
Summarizes recent research regarding organometallic derivatives of the transition elements.
Kaesz, Herbert D. J. Chem. Educ. 1963, 40, 159.
Organometallics |
Transition Elements |
Coordination Compounds |
Metals
Functionally-substituted aromatic silanes  Neville, Roy G.
The purpose of this article is to present a brief account of the functionally-substituted aromatic silanes.
Neville, Roy G. J. Chem. Educ. 1962, 39, 276.
Aromatic Compounds |
Organometallics