Foundation of the project Methodological particularities:

Foundation of the project Methodological particularities: www.phwiki.com

Foundation of the project Methodological particularities:

Turrentine, Jeff, Contributing Interior Design Reporter has reference to this Academic Journal, PHwiki organized this Journal A Novel Computer Lab Experiment Studies of Diels-Alder Reactions Stanislaw Skonieczny in addition to Mima Staikova Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6 Why are research in addition to teaching linked research – an élite activity scholars in addition to scientists held hostage in classrooms It is impossible to teach well without reflection, analysis, discussion. Relationship between research in addition to teaching The Diels-Alder Reaction: a diene + a dienophile transition state a cyclohexene derivative CHM 348F (Organic Reaction Mechanisms) : Lectures “Wet” labs Computer labs

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Dienes: Dienophiles: The most important orbitals in molecules as long as reactivity are the two so-called frontier orbitals. These are called the HOMO in addition to LUMO Molecular Orbitals – review LUMO = lowest unoccupied molecular orbital lowest energy orbital available LUMO receives electrons characteristic as long as electrophilic component HOMO = highest occupied molecular orbital electrons from the HOMO are donated most available as long as bonding most weakly held electrons characteristic as long as nucleophilic component Molecular Orbital Analysis of Diels-Alder reaction

Molecular Orbital Analysis – cont. There as long as e the reaction is said to be a “symmetry allowed” energy difference larger, less overlap – lower stabilization energy difference smaller, more overlap – more stabilization Molecular Orbital Analysis – cont. An example of a problem: Choose the best pair (one diene in addition to one dienophile) in addition to calculate the energies of HOMO in addition to LUMO. HOMO: -0.32348 -0.38622 -0.34261 -0.29698 LUMO: 0.1212 0.10006 0.19862 0.14441

HOMO LUMO dienes dienophiles An example of a problem: Choose the best pair (one diene in addition to one dienophile) in addition to calculate the energy difference. HOMO: -0.38622 -0.29698 LUMO: 0.10006 0.14441 E = 0.10006 – (-0.29698) = 0.39704 Hartree = 246.76 kcal/mol dienes dienophiles LUMO HOMO

exo product endo product Experiment: exo product more stable by 1.9 kcal/mol Ea lower as long as the endo product by 3.8 kcal/mol The Undergraduate Computer Lab – UCL Chemistry Department CHM 138 Introductory Organic Chemistry CHM 151 Chemistry: The Molecular Science CHM 247 Introductory Organic Chemistry CHM 348H Organic Reaction Mechanisms CHM 379 Biomolecular Chemistry CHM 415 Atmospheric Chemistry CHM 441F Applications of Spectroscopy to Organic Structure Determination CHM 443S Physical Organic Chemistry CHM 447F Bio-Organic Chemistry

Linux Computer Cluster Zeus Zeus configuration Main node: AMD Athlon 64 Dual 4800+ with 4 GB memory in addition to 250 GB HD Computational nodes: 10 Dual Athlon CPUs at 2 GHz, each with 1 GB memory. courtesy of Scott Browning Foundation of the project WebMo Pro interactive computer interface Hope College, Holl in addition to , MI, US http://www.webmo.net/index.html CHM348 Diels – Alder Reactions Computational Experiment using Gaussian03 suit of programs in addition to WebMo interface Be as long as e you begin: Read these instructions be as long as eh in addition to in addition to then start working. You have to complete 7 calculation jobs: 3 jobs as long as Geometry Optimization – 2 Reactants, 1 Product 1 job as long as Transition State Optimization 1 job as long as Transition State Vibrations 2 jobs as long as Molecular Orbital Calculations – one as long as each Reactant. All energies are calculated in Hartree (Atomic Unit as long as Energy) Conversion factor to kcal/mol: 1 Hartree = 627.51 kcal/mol

Select the appropriate substituents in the periodic table in addition to construct the substituted diene in addition to dienophile as long as your reaction. Prepare a separate job as long as each reactant. Building the Reactant Structures – cont. From the “Calculation” drop box select “Geometry Optimization”. Use “Theory”, “Basis set”, “Charge”, in addition to “Multiplicity” as shown above. When ready, send your job as long as calculation with the right blue arrow. Job Options as long as Reactant in addition to Product Geometry Optimization (3 jobs) Job Options When your job is calculated (it will take some time) it will show a “complete” status. Use the “view button” to see in addition to evaluate the results in addition to to use them as long as your next job preparation. Monitoring jobs progress

Evaluating Results Energy HOMO Energy LUMO Energy To view orbital, click here: Diene – HOMO Dienophile – LUMO Comparing HOMO – LUMO orbitals

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Diels Alder Reaction Endo Product Energy Energy 1.89 kcal/mol 0.51 kcal/mol B3LYP/6-31G -609.11 -609.10 -609.08 -609.07 -609.09 Reaction progress Methodological particularities: calculations are per as long as med at “research level” each student has a different set of compounds, works independently. project can be done in class or remotely at each student convenience.

Benefits to the educational process: relates the theoretical knowledge of the students gained in the courses to real problems, from the real environment. Benefits to the educational process: relates the theoretical knowledge of the students gained in the courses to real problems, from the real environment. facilitates the direct connection between macroscopic description of the chemistry phenomena in addition to the microscopic world of molecular interactions that drive chemical processes. Benefits to the educational process: relates the theoretical knowledge of the students gained in the courses to real problems, from the real environment. facilitates the direct connection between macroscopic description of the chemistry phenomena in addition to the microscopic world of molecular interactions that drive chemical processes. exposes the students to various theoretical methods in addition to approaches in solving scientific problems as a parallel/alternative to the experimental approaches presented in the chemistry course.

Acknowledgments Andrew P. Dicks Scott Browning, Jamie Donaldson Andrew Woolley Frank Buries, Michael Yoo $$ Chemistry Department, University of Toronto $$ Instructional Technology Courseware Development Fund

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