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A New "Bottom-Up" Framework for Teaching Chemical Bonding Tami Levy Nahum, Rachel Mamlok-Naaman, Avi Hofstein, and Leeor Kronik This article presents a general framework for bonding that can be presented at different levels of sophistication depending on the student's level and needs. The pedagogical strategy for teaching this model is a "bottom-up" one, starting with basic principles and ending with specific properties. Levy Nahum, Tami; Mamlok-Naaman, Rachel; Hofstein, Avi; Kronik, Leeor. J. Chem. Educ. 2008, 85, 1680.
Atomic Properties / Structure |
Covalent Bonding |
Ionic Bonding |
Lewis Structures |
Materials Science |
MO Theory |
Noncovalent Interactions
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Förster Resonance Energy Transfer and Conformational Stability of Proteins Katheryn M. Sanchez, Diana E. Schlamadinger, Jonathan E. Gable, and Judy E. Kim Describes the integration of absorption spectroscopy, fluorescence spectroscopy, and Frster resonance energy transfer (FRET) measurements to probe important topics in protein folding. Comparison of conformational stabilities of cytochrome c measured via two chemical denaturants illustrates important concepts in protein folding and intermolecular interactions. Sanchez, Katheryn M.; Schlamadinger, Diana E.; Gable, Jonathan E.; Kim, Judy E. J. Chem. Educ. 2008, 85, 1253.
Biophysical Chemistry |
Fluorescence Spectroscopy |
Proteins / Peptides |
Quantum Chemistry |
Resonance Theory |
Spectroscopy |
Thermodynamics |
UV-Vis Spectroscopy
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Acid-Catalyzed Enolization of β-Tetralone Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory. Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
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Exploring Solid-State Structure and Physical Properties: A Molecular and Crystal Model Exercise Thomas H. Bindel This laboratory allows students to examine relationships among the microscopicmacroscopicsymbolic levels using crystalline mineral samples and corresponding crystal models. The exercise also reinforces Lewis dot structures, VSEPR theory, and the identification of molecular and coordination geometries. Bindel, Thomas H. J. Chem. Educ. 2008, 85, 822.
Crystals / Crystallography |
Molecular Properties / Structure |
Molecular Modeling |
Solids |
VSEPR Theory |
Lewis Structures |
Physical Properties
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More on ClO and Related Radicals William B. Jensen The novel Lewis structure for the ClO radical and other related 13e isoelectronic species presented by Hirsch and Kobrak is identical to that proposed by Linnett over 40 years ago for the same species on the basis of his well-known double-quartet approach to Lewis structures. Jensen, William B. J. Chem. Educ. 2008, 85, 783.
Ionic Bonding |
Lewis Structures |
Free Radicals
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Six Pillars of Organic Chemistry Joseph J. Mullins This article focuses on a core set of conceptselectronegativity, polar covalent bonding, inductive and steric effects, resonance, and aromaticitythe proper application of which can explain and predict a wide variety of chemical, physical, and biological properties of molecules and conceptually unite important features of general, organic, and biochemistry. Mullins, Joseph J. J. Chem. Educ. 2008, 85, 83.
Bioorganic Chemistry |
Covalent Bonding |
Hydrogen Bonding |
Mechanisms of Reactions |
Periodicity / Periodic Table |
Reactive Intermediates |
Resonance Theory
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Lewis Structure Representation of Free Radicals Similar to ClO Warren Hirsch and Mark Kobrak An unconventional Lewis structure is proposed to explain the properties of the free radical ClO and a series of its isoelectronic analogues, particularly trends in the spin density of these species. Hirsch, Warren; Kobrak, Mark. J. Chem. Educ. 2007, 84, 1360.
Atmospheric Chemistry |
Computational Chemistry |
Covalent Bonding |
Free Radicals |
Lewis Structures |
Molecular Modeling |
MO Theory |
Valence Bond Theory
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Getting the Weights of Lewis Structures out of Hückel Theory: Hückel–Lewis Configuration Interaction (HL-CI) Stéphane Humbel A method to obtain the weights of Lewis structures from Hckel calculations is presented and tested against established ab initio methods. Humbel, Stéphane. J. Chem. Educ. 2007, 84, 1056.
Computational Chemistry |
Lewis Structures |
Theoretical Chemistry |
Quantum Chemistry |
Resonance Theory |
Valence Bond Theory
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Aromatic Bagels: An Edible Resonance Analogy Shirley Lin Describes a classroom demonstration involving the use of a bagel and cream cheese as an analogy for benzene that emphasizes the deficiencies of using a single Lewis structure to describe this structure. Lin, Shirley. J. Chem. Educ. 2007, 84, 779.
Aromatic Compounds |
Lewis Structures |
Resonance Theory |
Molecular Properties / Structure
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Predicting the Stability of Hypervalent Molecules Tracy A. Mitchell, Debbie Finocchio, and Jeremy Kua In this exercise, students use concepts in thermochemistry such as bond energy, ionization potentials, and electron affinities to predict the relative stability of two hypervalent molecules (PF5 and PH5) relative to their respective non-hypervalent counterparts. Mitchell, Tracy A.; Finocchio, Debbie; Kua, Jeremy. J. Chem. Educ. 2007, 84, 629.
Computational Chemistry |
Covalent Bonding |
Ionic Bonding |
Lewis Structures |
Molecular Modeling |
Calorimetry / Thermochemistry |
Molecular Properties / Structure
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Let Us Give Lewis Acid–Base Theory the Priority It Deserves Alan A. Shaffer The Lewis concept is simple yet powerful in its scope, and can be used to help beginning students understand reaction mechanisms more fully. However, traditional approaches to acid-base reactions at the introductory level ignores Lewis acid-base theory completely, focusing instead on proton transfer described by the Br?nsted-Lowry concept. Shaffer, Alan A. J. Chem. Educ. 2006, 83, 1746.
Acids / Bases |
Lewis Acids / Bases |
Lewis Structures |
Mechanisms of Reactions |
Molecular Properties / Structure |
VSEPR Theory |
Covalent Bonding |
Brønsted-Lowry Acids / Bases
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More on the Nature of Resonance Robert C. Kerber The author continues to find the use of delocalization preferable to resonance. Kerber, Robert C. . J. Chem. Educ. 2006, 83, 1291.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Resonance Theory |
Nomenclature / Units / Symbols
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More on the Nature of Resonance William B. Jensen Supplements a recent article on the interpretation of resonance theory with three additional observationsone historical and two conceptual. Jensen, William B. J. Chem. Educ. 2006, 83, 1290.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
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A Novel Exploration of the Hartree–Fock Homolytic Bond Dissociation Problem in the Hydrogen Molecule by Means of Electron Localization Measures Eduard Matito, Miquel Duran, and Miquel Solà Provides new insight into the restricted HartreeFock (HF) method of homolytic bond dissociation by using localization and delocalization indices defined in the framework of the atoms-in-molecules theory to analyze homolytic bond dissociation in the hydrogen molecule. Matito, Eduard; Duran, Miquel; Solà, Miquel. J. Chem. Educ. 2006, 83, 1243.
Computational Chemistry |
Learning Theories |
Lewis Structures |
Molecular Properties / Structure |
Quantum Chemistry |
Theoretical Chemistry
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Lecture Templates: Convenient Partial Lecture Delivery System Elzbieta Cook and Robert L. Cook Reports on the use of two forms of PowerPoint lecture presentationsa complete version used by the lecturer and a corresponding partial version available in advance to students. Pre-prepared lecture presentations allow for the sharing of lecture materials among teaching faculty and ensure consistency among several lecture sections in team taught courses. Cook, Elzbieta; Cook, Robert L. J. Chem. Educ. 2006, 83, 1176.
Equilibrium |
Lewis Structures |
Professional Development
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Valence, Oxidation Number, and Formal Charge: Three Related but Fundamentally Different Concepts Gerard Parkin The purpose of this article is to clarify the terms valence, oxidation number, coordination number, formal charge, and number of bonds and illustrate how the valence of an atom in a molecule provides a much more meaningful criterion for establishing the chemical reasonableness of a molecule than does the oxidation number. Parkin, Gerard. J. Chem. Educ. 2006, 83, 791.
Coordination Compounds |
Covalent Bonding |
Lewis Structures |
Oxidation State |
Nomenclature / Units / Symbols
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If It's Resonance, What Is Resonating? Robert C. Kerber This article reviews the origin of the terminology associated with the use of more than one Lewis-type structure to describe delocalized bonding in molecules and how the original usage has evolved to reduce confusion Kerber, Robert C. . J. Chem. Educ. 2006, 83, 223.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
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Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure" Gordon H. Purser Weinhold makes four major criticisms of my article. I shall address each of these criticisms. Purser, Gordon H. J. Chem. Educ. 2005, 82, 528.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
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Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure" Frank Weinhold Some time ago in this Journal, Purser expressed strong views on the proper teaching of Lewis structures, as summarized in the quoted title. Because his criticisms are based on substantial factual misrepresentations and errors, it seemed desirable to call attention to a few of the conspicuous misstatements in order that readers may judge the opinions and conclusions from a more informed perspective. Weinhold, Frank. J. Chem. Educ. 2005, 82, 527.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
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The Concept of Oxidation States in Metal Complexes Dirk Steinborn After a brief historical survey, basic considerations are given to assign oxidation numbers of atoms in molecules on the basis of their Lewis structures by splitting shared electrons in covalent bonds heterolytically. Advantages over the frequently used method to assign oxidation numbers by using a set of hierarchical rules are demonstrated for some nonmetal compounds. Assignment of oxidation numbers of metals is systematically worked out for metal complexes with n-, pi-, and s-ligands. Furthermore, it is shown how the concept of oxidation states is embedded in the teaching process of molecular chemistry for early chemistry students. Steinborn, Dirk. J. Chem. Educ. 2004, 81, 1148.
Covalent Bonding |
Coordination Compounds |
Oxidation / Reduction |
Lewis Structures |
Metals |
Crystal Field / Ligand Field Theory
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Writing Electron Dot Structures Kenneth R. Magnell Drill with feedback for students learning to write electron dot structures. Magnell, Kenneth R. J. Chem. Educ. 2003, 80, 711.
Covalent Bonding |
Lewis Structures |
Resonance Theory |
Enrichment / Review Materials
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The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena Joel Rosenthal and David I. Schuster Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds. Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003, 80, 679.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis |
Electrophilic Substitution |
Enrichment / Review Materials |
Resonance Theory
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The Molecular Model Game Stephanie A. Myers Student teams must draw Lewis structures and build models of various molecules and polyatomic ions; different team members have different responsibilities. Myers, Stephanie A. J. Chem. Educ. 2003, 80, 423.
Molecular Properties / Structure |
Covalent Bonding |
Lewis Structures |
VSEPR Theory |
Enrichment / Review Materials
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Chemical Bonding and Molecular Geometry: From Lewis to Electron Densities (Gillespie and Popelier) Daniel Rabinovich Overview of the classical and modern concepts used to explain and predict molecular geometries of the nonmetallic elements and their compounds. Rabinovich, Daniel. J. Chem. Educ. 2003, 80, 31.
Covalent Bonding |
Molecular Properties / Structure |
VSEPR Theory |
Valence Bond Theory |
Lewis Structures |
Nonmetals
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How We Teach Molecular Structure to Freshmen Michael O. Hurst Examination of how textbooks discuss various aspects of molecular structure; conclusion that much of general chemistry is taught the way it is for historical and not pedagogical reasons. Hurst, Michael O. J. Chem. Educ. 2002, 79, 763.
Covalent Bonding |
Atomic Properties / Structure |
Molecular Properties / Structure |
Lewis Structures |
VSEPR Theory |
Valence Bond Theory |
MO Theory
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Keto-Enol Tautomers in a Carbonyl Phosphonium Salt David E. Berry and G. W. Patenaude Observations of keto-enol tautomers of a phosphonium ion. Berry, David E.; Patenaude, G. W. J. Chem. Educ. 2002, 79, 498.
Synthesis |
NMR Spectroscopy |
Organometallics |
Resonance Theory
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The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber Synthesis, purification, and characterization of three esters. Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002, 79, 218.
Mechanisms of Reactions |
Molecular Properties / Structure |
Resonance Theory |
Reactive Intermediates |
Equilibrium |
Esters |
Aromatic Compounds |
Brønsted-Lowry Acids / Bases
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The Role of Lewis Structures in Teaching Covalent Bonding S. R. Logan Difficulties with the Lewis theory of covalent bonding and upgrading it to the Molecular Orbital theory. Logan, S. R. J. Chem. Educ. 2001, 78, 1457.
Covalent Bonding |
MO Theory |
Nonmajor Courses |
Learning Theories |
Lewis Structures |
Molecular Properties / Structure
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Lewis Structures in General Chemistry: Agreement between Electron Density Calculations and Lewis Structures Gordon H. Purser The internuclear electron densities of a series of X-O bonds (where X = P, S, or Cl) are calculated using quantum mechanics and compared to Lewis structures for which the formal charges have been minimized; a direct relationship is found between the internuclear electron density and the bond order predicted from Lewis structures in which formal charges are minimized. Purser, Gordon H. J. Chem. Educ. 2001, 78, 981.
Covalent Bonding |
Computational Chemistry |
Molecular Properties / Structure |
Lewis Structures |
Quantum Chemistry
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Drawing Lewis Structures from Lewis Symbols: A Direct Electron-Pairing Approach Wan-Yaacob Ahmad and Mat B. Zakaria We describe a different, more student-friendly approach to writing Lewis structures for covalent molecules and ions based on Lewis theory and Abegg's rule. Several rules for selecting central atoms are provided. Separate sets of rules are provided for diatomic molecules and ions and for polyatomic molecules and ions. Ahmad, Wan-Yaacob; Zakaria, Mat B. J. Chem. Educ. 2000, 77, 329.
Molecular Properties / Structure |
Lewis Structures
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Lewis Structures Are Models for Predicting Molecular Structure, Not Electronic Structure Gordon H. Purser This article argues against a close relationship between Lewis dot structures and electron structure obtained from quantum mechanical calculations. Lewis structures are a powerful tool for structure prediction, though they are classical models of bonding and do not predict electronic structure. Purser, Gordon H. J. Chem. Educ. 1999, 76, 1013.
Molecular Properties / Structure |
Covalent Bonding |
Computational Chemistry |
Quantum Chemistry |
MO Theory |
Learning Theories |
Lewis Structures |
Molecular Modeling
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The "Big Dog-Puppy Dog" Analogy for Resonance Todd P. Silverstein In this analogy, puppy dogs are restricted to a specific dog run; they represent s-bond electron pairs. Big dogs are allowed to roam freely over several consecutive dog runs; they represent delocalized p-bond electron pairs. By adding a bunny rabbit who is chased by the big dog, the analogy can be expanded to account for delocalized formal charge in a resonance hybrid. Silverstein, Todd P. J. Chem. Educ. 1999, 76, 206.
Covalent Bonding |
Learning Theories |
Resonance Theory |
Molecular Properties / Structure
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Simplified Lewis Structure Drawing for Nonscience Majors Barnabe B. Miburo Lewis structures are drawn using a simplified novel method with the following features: 1) the atoms used are brought in carrying all their valence electrons; 2) bonds are created by pairing up valence electrons between the central atoms and peripheric atoms; 3) anions are formed by addition of electrons to single electrons on appropriate atoms, while cations are formed by removal of single electrons. Miburo, Barnabe B. J. Chem. Educ. 1998, 75, 317.
Learning Theories |
Lewis Structures |
Nonmajor Courses |
Molecular Properties / Structure
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Making Organic Concepts Visible Robert S. H. Liu and Alfred E. Asato Graphic illustrations, with a Hawaiian flavor, have been introduced to clarify the following concepts encountered in introductory organic chemistry: functional groups, resonance structures, polarizability, ionization in mass spectroscopy and difference in reactivities between alkyl and vinyl halides Liu, Robert S. H.; Asato, Alfred E. J. Chem. Educ. 1997, 74, 783.
Mechanisms of Reactions |
Resonance Theory
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Experimental Illustration of the Utility of Lewis Structures: An FTIR Experiment for Introductory Chemistry James E. Swartz and Kurt Schladetzky An experiment is described in which students record the FTIR spectra of a series of organic liquids which contain a carbonyl group and to predict the strength of the carbonyl bonds based upon drawing and examination of various Lewis structures. Swartz, James E.; Schladetzky, Kurt. J. Chem. Educ. 1996, 73, 188.
Fourier Transform Techniques |
Aldehydes / Ketones |
Lewis Structures
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Lewis Structures of Oxygen Compounds of 3p-5p Nonmetals Darel K. Straub Procedure for writing Lewis structures of oxygen compounds of 3p-5p nonmetals. Straub, Darel K. J. Chem. Educ. 1995, 72, 889.
Lewis Structures |
Molecular Properties / Structure |
Covalent Bonding |
Main-Group Elements
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Common Textbook and Teaching Misrepresentations of Lewis Structures Laila Suidan, Jay K. Badenhoop, Eric D. Glendening, and Frank Weinhold Clarifying leading Lewis structures using computational software. Suidan, Laila; Badenhoop, Jay K.; Glendening, Eric D.; Weinhold, Frank. J. Chem. Educ. 1995, 72, 583.
Lewis Structures |
Covalent Bonding |
Quantum Chemistry |
Molecular Properties / Structure
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Lewis Structures of Boron Compounds Involving Multiple Bonding Straub, Darel K. Considers evidence for multiple bonding in boron compounds and supposed exceptions to the octet rule. Straub, Darel K. J. Chem. Educ. 1995, 72, 494.
Lewis Structures |
Covalent Bonding
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Using Formal Charges in Teaching Descriptive Inorganic Chemistry DeWit, David G. Using the concept of formal charges to predict bond properties, determine molecular structure, and explain reactivities and the tendency to polymerize. DeWit, David G. J. Chem. Educ. 1994, 71, 750.
Descriptive Chemistry |
Molecular Properties / Structure |
Lewis Structures |
Polymerization
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The Lewis Structure: An Expanded Perspective Reed, James L. A simple bridge between the molecular orbital and valence bond models. Reed, James L. J. Chem. Educ. 1994, 71, 98.
Lewis Structures |
Covalent Bonding |
MO Theory |
Molecular Properties / Structure
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A New Approach To Teaching Organic Chemical Mechanisms Wentland, Stephen H. Describing the mechanisms of organic reactions using five simple steps or operations. Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
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Do our students really understand the Hammett equation? Schwan, Adrian L. In this author's experience, many students can proceed through text questions dealing with the Hammett equation without having a full understanding of the Hammett analysis. He offers a question that enables students to gain a better appreciation of this concept. Schwan, Adrian L. J. Chem. Educ. 1993, 70, 1001.
Chemometrics |
Resonance Theory |
Constitutional Isomers
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Writing Lewis structures Weeks, Daniel In response to a problem posed in a June 1991 article, this author points to a solution he authored 17 years ago. Weeks, Daniel J. Chem. Educ. 1993, 70, 519.
Lewis Structures
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Davidsoniana Jones and the cult of the curved arrow Brisbois, Ronald G. Puzzles to help students understand valence bond theory, resonance, and tautomerism. Brisbois, Ronald G. J. Chem. Educ. 1992, 69, 971.
Resonance Theory
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Drawing Lewis structures: A step-by-step approach Ahmad, Wan-Yaacob; Omar, Siraj A simple step-by-step approach for deriving Lewis structures for students studying introductory chemistry. Ahmad, Wan-Yaacob; Omar, Siraj J. Chem. Educ. 1992, 69, 791.
Lewis Structures |
VSEPR Theory |
Molecular Properties / Structure
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Spontaneous detonation of a mixture of two odd electron gases Briggs, Thomas S. Instructions for safe detonation of ClO2 and NO (the fastest known reaction between two stable molecules at room temperature). Briggs, Thomas S. J. Chem. Educ. 1991, 68, 938.
Reactions |
Resonance Theory
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Explaining resonance - a colorful approach Abel, Kenton B.; Hemmerlin, William M. An analogy using color to help students understand that a resonance molecule does not shift back and forth between Lewis Structures, but is in fact a hybrid of the two structures. Abel, Kenton B.; Hemmerlin, William M. J. Chem. Educ. 1991, 68, 834.
Resonance Theory |
Lewis Structures |
Molecular Properties / Structure
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Lewis structures, formal charge, and oxidation numbers: A more user-friendly approach Packer, John E.; Woodgate, Sheila D. This paper presents a set of rules for writing Lewis structures requiring only the ability to add, subtract, count, and know the number of valence electrons of neutral atoms. Packer, John E.; Woodgate, Sheila D. J. Chem. Educ. 1991, 68, 456.
Lewis Structures |
Oxidation State
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Lone electron motion delocalization and relocalization to write Lewis structures McGoran, Ernest C. A protocol for writing Lewis electron dot structures that attempts to unite the standard symbolism with our more contemporary interpretations given to the covalent bond. McGoran, Ernest C. J. Chem. Educ. 1991, 68, 19.
Lewis Structures
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A new approach to the generation of sigma complex structures Young, Joseph G. An alternative to the electron pushing approach for determining intermediate resonance structures for electrophilic aromatic substitutions. Young, Joseph G. J. Chem. Educ. 1990, 67, 550.
Aromatic Compounds |
Electrophilic Substitution |
Resonance Theory |
Mechanisms of Reactions
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A visual aid for teaching the resonance concept Delvigne, Francis Using "dot clouds" to represent electron densities and resonance in structures such as benzene. Delvigne, Francis J. Chem. Educ. 1989, 66, 461.
Resonance Theory |
Aromatic Compounds
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Teaching a model for writing Lewis structures Pardo, Juan Quilez A general procedure for the representation of Lewis structures. Pardo, Juan Quilez J. Chem. Educ. 1989, 66, 456.
Lewis Structures |
Molecular Properties / Structure |
Molecular Modeling
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The chemical bond DeKock, Roger L. Overview of the chemical bond; considers ionic bonds, covalent bonds, Lewis electron dot structures, polar molecules and hydrogen bonds, and bonding in solid-state elements. DeKock, Roger L. J. Chem. Educ. 1987, 64, 934.
Ionic Bonding |
Covalent Bonding |
Hydrogen Bonding |
Solid State Chemistry |
Lewis Structures |
Molecular Properties / Structure
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Lewis structures for compounds with expanded octets Malerich, Charles J. A simple method for recognizing expanded octets given only the molecular formula of the compound. Malerich, Charles J. J. Chem. Educ. 1987, 64, 403.
Lewis Structures |
Molecular Properties / Structure
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Teaching the concept of resonance with transparent overlays Richardson, W. S. The overlap method can be useful in the development of the concept of a partial charge on the atoms of an ion. Richardson, W. S. J. Chem. Educ. 1986, 63, 518.
Resonance Theory |
Molecular Properties / Structure
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The arithmetic of aromaticity Glidewell, Christopher; Lloyd, Douglas In this article, the authors explore an aspect of conjugated systems that have received little attention, namely polycyclic hydrocarbons. Glidewell, Christopher; Lloyd, Douglas J. Chem. Educ. 1986, 63, 306.
Alkanes / Cycloalkanes |
Resonance Theory |
Aromatic Compounds
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Drawing Lewis structures without anticipating octets Carroll, James Allen This note presents a discussion of several examples of appropriate Lewis structures and the fine structural predictions that are possible. Carroll, James Allen J. Chem. Educ. 1986, 63, 28.
Lewis Structures |
VSEPR Theory |
Molecular Modeling
|
Gilbert Newton Lewis and the amazing electron dots Tiernan, Natalie Foote Development of electron dot formulas by and brief biography of Gilbert Lewis. Tiernan, Natalie Foote J. Chem. Educ. 1985, 62, 569.
Lewis Structures
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The "6N+2 Rule" for writing Lewis octet structures Zandler, Melvin E.; Talaty, Erach R. Applying the "6N+2 Rule" to writing Lewis octet structures. Zandler, Melvin E.; Talaty, Erach R. J. Chem. Educ. 1984, 61, 124.
Lewis Structures |
Molecular Properties / Structure
|
Another procedure for writing Lewis structures Clark, Thomas J. A simple procedure for writing a correct Lewis structure for a molecule or ion containing only s- and p-block elements. Clark, Thomas J. J. Chem. Educ. 1984, 61, 100.
Lewis Structures |
Molecular Properties / Structure
|
The synthesis of 4,6,8-trimethylazulene: an organic laboratory experiment Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott A procedure for a two-step synthesis of 4,6,8-trimethylazulene. Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott J. Chem. Educ. 1983, 60, 510.
Synthesis |
Heterocycles |
Aromatic Compounds |
Resonance Theory |
Chromatography
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Electron-dot structures of O2 and NO: Ignored gems from the work of J. W. Linnett Levy, Jack B. The presented treatment makes it easier for students to make predictive models with electron-dot structures. Levy, Jack B. J. Chem. Educ. 1983, 60, 404.
Lewis Structures |
MO Theory |
Covalent Bonding
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Structure-resonance theory for pericyclic transition states Herndon, William C. The purpose of this article is to show that structure-resonance theory can be used to understand the effects of structure or substituents on the rates of thermal pericyclic reactions. Herndon, William C. J. Chem. Educ. 1981, 58, 371.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure
|
Computer instruction in Lewis structures of simple molecules Bendall, Victor I. 7. Bits and pieces, 1. Bendall, Victor I. J. Chem. Educ. 1980, 57, 252.
Lewis Structures |
Molecular Properties / Structure
|
The aromatic ring Kolb, Doris Historic analysis and attempts to explain the structure of benzene, the concept of resonance, Huckel's rule, polycyclic aromatic compounds, non-classical aromatic compounds, and a definition for aromaticity. Kolb, Doris J. Chem. Educ. 1979, 56, 334.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
|
Electrons, bonding, orbitals, and light: A unified approach to the teaching of structure and bonding in organic chemistry courses Lenox, Ronald S. A suggested list of topics and methods for teaching introductory organic students bonding concepts. Lenox, Ronald S. J. Chem. Educ. 1979, 56, 298.
Atomic Properties / Structure |
Lewis Structures |
Spectroscopy |
Covalent Bonding
|
Back-of-the-envelope molecular orbital "calculations". Using bond orbitals and group theory Davidson, Robert B. Outlines the prediction of orbital symmetries from Lewis structures using bond orbitals and group theory. Davidson, Robert B. J. Chem. Educ. 1977, 54, 531.
Group Theory / Symmetry |
Lewis Structures |
MO Theory |
Atomic Properties / Structure |
VSEPR Theory
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Frank C. Whitmore and the first successful explanation of some intramolecular rearrangements Saltzman, Martin D. In 1932 Frank C. Whitmore presented a beautifully succinct and detailed pathway using the octet concept of Lewis to show the common basis of many intramolecular rearrangements discovered during the 19th and early 20th centuries. Saltzman, Martin D. J. Chem. Educ. 1977, 54, 25.
Molecular Properties / Structure |
Covalent Bonding |
Lewis Structures
|
A direct calorimetric demonstration of resonance energy in the benzene nucleus van Vugt, W. H.; Mosselman, C. This calorimetric experiment is intended as a first contact in chemical education with the aromaticity concept. van Vugt, W. H.; Mosselman, C. J. Chem. Educ. 1975, 52, 746.
Calorimetry / Thermochemistry |
Resonance Theory
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An alternative procedure to writing Lewis structures Imkampe, Karl Using simple molecular orbital pictures to represent all the resonance structures of larger organic molecules. Imkampe, Karl J. Chem. Educ. 1975, 52, 429.
Lewis Structures |
Molecular Properties / Structure |
Resonance Theory
|
Resonance theory and the enumeration of Kekule structures Herndon, William C. The formulation of resonance theory as it is practiced today is explicated in the well-known books by Pauling and Wheland. Study of these texts show that resonance theory are so drastic that many theoreticians are loathe to ascribe validity to the less rigorous method. Herndon, William C. J. Chem. Educ. 1974, 51, 10.
Resonance Theory |
Theoretical Chemistry |
Aromatic Compounds |
Molecular Properties / Structure
|
Lewis structures and the octet rule. An automatic procedure for writing canonical forms Lever, A. B. P. Canonical Lewis structures may be derived by a simple, almost automatic, procedure, enabling one to write down, correctly and rapidly, the resonance forms of any short period species. Lever, A. B. P. J. Chem. Educ. 1972, 49, 819.
Lewis Structures
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The determination of the resonance energy of benzene. A physical chemistry laboratory experiment Stevenson, Gerald R. This procedure relies on calorimetry to measure the resonance energy of benzene, a useful way to relate the concepts of aromaticity and resonance energy to experimental thermodynamics. Stevenson, Gerald R. J. Chem. Educ. 1972, 49, 781.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure |
Calorimetry / Thermochemistry |
Thermodynamics
|
Selective reduction of dinitrobenzenes. An organic laboratory experiment Idoux, John P.; Plain, Wendell Different students are assigned different reducing agents and asked to explain why their particular selective reduction occurs as their results indicate. Idoux, John P.; Plain, Wendell J. Chem. Educ. 1972, 49, 133.
Aromatic Compounds |
Resonance Theory |
Oxidation / Reduction
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Guanidine, trimethylenemethane, and "Y-delocalization." Can acyclic compounds have "aromatic" stability? Gund, Peter It appears that the Y-shaped configuration of 6 pi electrons as found in guanidine derivatives is an exceptionally stable one. Gund, Peter J. Chem. Educ. 1972, 49, 100.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory |
MO Theory
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Evidence of d pi-acceptor resonance in halogen substituents Abdulla, Riaz F. The association of various structural and dynamic phenomena through the postulate of d pi resonance has potential additional predictive value. Abdulla, Riaz F. J. Chem. Educ. 1972, 49, 64.
Resonance Theory |
Mechanisms of Reactions
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Dewar resonance energy Baird, N. C. In the present paper, some of the general properties of the Dewar Resonance Energy definition are developed. In particular, the DRE value for a compound is shown to be independent of the numerical values used to bond energies, and the use of DRE in judging the aromaticity of organic molecules is illustrated. Baird, N. C. J. Chem. Educ. 1971, 48, 509.
Resonance Theory |
Aromatic Compounds |
Molecular Properties / Structure
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Understanding a culprit before eliminating it. An application of Lewis acid-base principles to atmospheric SO2 as a pollutant Brasted, Robert C. The SO2 molecule offers ample opportunities for teaching practical chemistry. [Debut of first run. This feature reappeared in 1986.] Brasted, Robert C. J. Chem. Educ. 1970, 47, 447.
Acids / Bases |
Lewis Acids / Bases |
Atmospheric Chemistry |
Mechanisms of Reactions |
Reactions |
Applications of Chemistry |
Lewis Structures |
Molecular Properties / Structure
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Cross conjugation Phelan, Nelson F.; Orchin, Milton Although qualitative conclusions may be obtained by judicious use of simple resonance theory, even in simple systems the electron distribution and extent of conjugation between the nonconjugated centers in cross conjugation is most effectively illustrated by molecular orbital descriptions. Phelan, Nelson F.; Orchin, Milton J. Chem. Educ. 1968, 45, 633.
Valence Bond Theory |
MO Theory |
Resonance Theory
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The electron repulsion theory of the chemical bond. II. An alternative to resonance hybrids Luder, W. F. The author proposes the electron repulsion theory of the chemical bond as an alternative to resonance hybrids. Luder, W. F. J. Chem. Educ. 1967, 44, 269.
Covalent Bonding |
Resonance Theory
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Electronic interactions between nonconjugated groups Ferguson, Lloyd N.; Nnadi, John C. The purpose of this paper is to discuss some of the different molecular systems in which electronic interactions between classically nonconjugated groups are explicable in terms of molecular orbital theory as well as nonclassical resonance theory. Ferguson, Lloyd N.; Nnadi, John C. J. Chem. Educ. 1965, 42, 529.
MO Theory |
Resonance Theory |
Molecular Properties / Structure
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Rules for molecular orbital structures Meislich, Herbert In view of the fact that molecular orbital theory makes more correct predictions and avoids the misconceptions that arise in the minds of novice students when they are exposed to resonance theory, it would be better to use M.O. theory as much as possible in teaching organic chemistry. Meislich, Herbert J. Chem. Educ. 1963, 40, 401.
MO Theory |
Resonance Theory
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The electronic structures and stereochemistry of NO2+, NO2, and NO2- Panckhurst, M. H. A comparison of the electronic structures and stereochemistry of NO2+, NO2, and NO2-. Panckhurst, M. H. J. Chem. Educ. 1962, 39, 270.
Stereochemistry |
Molecular Properties / Structure |
Resonance Theory
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The contributions of Fritz Arndt to resonance theory Campaigne, E. Examines the contribution of Fritz Arndt to resonance theory and his work regarding the nature of bonds in pyrone ring systems. Campaigne, E. J. Chem. Educ. 1959, 36, 336.
Resonance Theory |
Aromatic Compounds |
Covalent Bonding
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Theoretical chemistry in Russia Hunsberger, I. Moyer Examines contributions to organic structural theory and Russian criticisms of resonance theory. Hunsberger, I. Moyer J. Chem. Educ. 1954, 31, 504.
Resonance Theory
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Kekule's theory of aromaticity Gero, Alexander Examines what Kekule really wrote in his famous paper on the structure of benzene. Gero, Alexander J. Chem. Educ. 1954, 31, 201.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
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Predicting reactions of a resonance hybrid from minor canonical structures Gero, Alexander Little effort seems to have been made to set up any general rules on the relative contributions of the several structural formulas (canonical structures) used to represent a resonance hybrid to the reactions of the hybrid. Gero, Alexander J. Chem. Educ. 1954, 31, 136.
Resonance Theory |
Mechanisms of Reactions
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Letters Bent, Richard L. Addresses issues raised regarding an earlier paper on isomerism and mesomerism. Bent, Richard L. J. Chem. Educ. 1953, 30, 648.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
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Letters Ferreira, Ricardo Carvalho Identifies some inconsistencies in an earlier paper on isomerism and mesomerism. Ferreira, Ricardo Carvalho J. Chem. Educ. 1953, 30, 647.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
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Letters Wolfrom, Melville L. The author encourages American chemists to familiarize themselves with the conventions of representing configurational formulas. Wolfrom, Melville L. J. Chem. Educ. 1953, 30, 479.
Molecular Modeling |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
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Aspects of isomerism and mesomerism. I. (a) Formulas and their meaning (b) Mesomerism Bent, Richard L. Examines molecular, empirical, structural, configurational, and projection formulas, as well as mesomerism (electronic isomers) and various types of resonance. Bent, Richard L. J. Chem. Educ. 1953, 30, 220.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
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Letters Brescia, Frank The author calls for someone to invent another term for the word resonance as applied to the field of molecular structure. Brescia, Frank J. Chem. Educ. 1952, 29, 261.
Resonance Theory |
Nomenclature / Units / Symbols |
Molecular Properties / Structure
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The concept of resonance energy in elementary organic chemistry Gero, Alexander The author describes an empirically-based presentation of resonance energy that is perfectly within reach of introductory organic students. Gero, Alexander J. Chem. Educ. 1952, 29, 82.
Resonance Theory
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About a machistic theory in chemistry and its propagandists Tatevskii, V. M.; Shakhparanov, M. I. Russian scientists attack the resonance theory and the use of resonance structures. Tatevskii, V. M.; Shakhparanov, M. I. J. Chem. Educ. 1952, 29, 13.
Molecular Properties / Structure |
Resonance Theory
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The present state of the chemical structural theory Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh. Several members of the Russian Academy of Sciences attack the resonance theory and resonance structures. Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh. J. Chem. Educ. 1952, 29, 2.
Molecular Properties / Structure |
Resonance Theory
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