51
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

A Molecular Electron Density Theory Study of the Polar Diels-Alder Reaction of Naphtoquinone:Cr(CO)3 Complex with Cyclic Dienes

, &
Pages 8065-8081 | Received 14 Jul 2022, Accepted 02 Nov 2022, Published online: 12 Nov 2022

References

  • O. Diels, and K. Alder, “Synthesen in Der Hydroaromatischen Reihe,” Justus Liebig’s Annalen Der Chemie 460, no. 1 (1928): 98–122.
  • W. Carruthers, Some Modern Methods of Organic Synthesis. 2nd ed. (Cambridge: Cambridge University Press, 1978).
  • W. Carruthers, Cycloaddition Reactions in Organic Synthesis. (Pergamon: Oxford, 1990).
  • D. Rowley, and H. Steiner, “Kinetics of Diene Reactions at High Temperatures,” Discussions of the Faraday Society 10 (1951): 198–213.
  • L. R. Domingo, and J. A. Sáez, “Understanding the Mechanism of Polar Diels–Alder Reactions,” Organic & Biomolecular Chemistry 7, no. 17 (2009): 3576–83.
  • L. R. Domingo, “A New C-C Bond Formation Model Based on the Quantum Chemical Topology of Electron Density,” RSC Adv. 4, no. 61 (2014): 32415–28.
  • L. R. Domingo, M. Ríos-Gutiérrez, and P. Pérez, “Unveiling the Lewis Acid Catalysed Diels–Alder Reactions through the Molecular Electron Density Theory,” Molecules 25, no. 11 (2020): 2535.
  • R. G. Parr, L. v Szentpaly, and S. Liu, “Electrophilicity Index,” Journal of the American Chemical Society 121, no. 9 (1999): 1922–4.
  • L. R. Domingo, E. Chamorro, and P. Pérez, “Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study,” The Journal of Organic Chemistry 73, no. 12 (2008): 4615–24.
  • R. G. Parr, and W. Yang, Density Functional Theory of Atoms and Molecules. (Oxford: Oxford University Press, 1989).
  • L. R. Domingo, M. Ríos-Gutiérrez, and P. Pérez, “Applications of the Conceptual Density Functional Indices to Organic Chemistry Reactivity,” Molecules 21, no. 6 (2016): 748.
  • L. R. Domingo, and M. Ríos-Gutiérrez, “Application of Reactivity Indices in the Study of Polar Diels–Alder Reactions,” in Conceptual Density Functional Theory: Towards a New Chemical Reactivity Theory, edited by Liu Shubin. vol. 2, (Weinheim, Germany: WILEY-VCH GmbH, 2022), 481–502.
  • M. Rosillo, G. Domínguez, and J. Pérez-Castells, “Chromium Arene Complexes in Organic Synthesis,” Chemical Society Reviews 36, no. 10 (2007): 1589–604.
  • D. Möhring, M. Nieger, B. Lewall, and K. H. Dötz, “Tricarbonyl(Naphthoquinone) Chromium: Synthesis and Application in [4 + 2] Cycloaddition Reactions,” European Journal of Organic Chemistry 2005, no. 12 (2005): 2620–8.
  • L. R. Domingo, “Molecular Electron Density Theory: A Modern View of Reactivity in Organic Chemistry,” Molecules 21, no. 10 (2016): 1319.
  • L. R. Domingo, M. J. Aurell, and M. Ríos-Gutiérrez, “Does Cr(CO)3 Really Behave as Catalyst in the Diels-Alder Reaction of Styrene with Cyclopentadiene? A MEDT Study,” ChemistrySelect 7, no. 24 (2022): e202201435.
  • J.-D. Chai, and M. Head-Gordon, “Long-Range Corrected Hybrid Density Functionals with Damped Atom–Atom Dispersion Corrections,” Physical Chemistry Chemical Physics : PCCP 10, no. 44 (2008): 6615–20.
  • M. J. Hehre, L. Radom, PvR. Schleyer, and J. Pople, Ab Initio Molecular Orbital Theory. (New York: Wiley, 1986).
  • H. B. Schlegel, “Optimization of Equilibrium Geometries and Transition Structures,” Journal of Computational Chemistry 3, no. 2 (1982): 214–8.
  • H. B. Schlegel, In Modern Electronic Structure Theory, edited by Yarkony D. R, (Singapore: World Scientific Publishing, 1994).
  • K. Fukui, “Formulation of the Reaction Coordinate,” The Journal of Physical Chemistry 74, no. 23 (1970): 4161–3.
  • C. González, and H. B. Schlegel, “Reaction Path following in Mass-Weighted Internal Coordinates,” The Journal of Physical Chemistry 94, no. 14 (1990): 5523–7.
  • C. González, and H. B. Schlegel, “Improved Algorithms for Reaction Path following: higher‐Order Implicit Algorithms,” The Journal of Chemical Physics 95, no. 8 (1991): 5853–60.
  • J. Tomasi, and M. Persico, “Molecular Interactions in Solution: And Overview of Methods Based on Continuous Distributions of the Solvent,” Chemical Reviews 94, no. 7 (1994): 2027–94.
  • BYa Simkin, and I. I. Sheikhet, Quantum Chemical and Statistical Theory of Solutions– Computational Approach, (London: Ellis Horwood, 1995).
  • M. Cossi, V. Barone, R. Cammi, and J. Tomasi, “Ab Initio Study of Solvated Molecules: A New Implementation of the Polarizable Continuum Model,” Chemical Physics Letters 255, no. 4-6 (1996): 327–35.
  • E. Cances, B. Mennucci, and J. Tomasi, “A New Integral Equation Formalism for the Polarizable Continuum Model: Theoretical Background and Applications to Isotropic and Anisotropic Dielectrics,” The Journal of Chemical Physics 107, no. 8 (1997): 3032–41.
  • V. Barone, M. Cossi, and J. Tomasi, “Geometry Optimization of Molecular Structures in Solution by the Polarizable Continuum Model,” Journal of Computational Chemistry 19, no. 4 (1998): 404–17.
  • A. E. Reed, R. B. Weinstock, and F. Weinhold, “Natural Population Analysis,” The Journal of Chemical Physics 83, no. 2 (1985): 735–46.
  • A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint,” Chemical Reviews 88, no. 6 (1988): 899–926.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al. Gaussian 16, Revision A.03. (Wallingford CT: Gaussian, Inc., 2016).
  • A. D. Becke, and K. E. Edgecombe, “A Simple Measure of Electron Localization in Atomic and Molecular-Systems,” The Journal of Chemical Physics 92, no. 9 (1990): 5397–403.
  • S. Noury, X. Krokidis, F. Fuster, and B. Silvi, “Computational Tools for the Electron Localization Function Topological Analysis,” Computers & Chemistry 23, no. 6 (1999): 597–604.
  • R. Dennington, T. Keith, and J. Millam, GaussView, Version 6.0, R. (Shawnee Mission: Semichem Inc., 2016).
  • B. Silvi, and A. Savin, “Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions,” Nature 371, no. 6499 (1994): 683–6.
  • R. G. Parr, and R. G. Pearson, “Absolute Hardness: Companion Parameter to Absolute Electronegativity,” Journal of the American Chemical Society 105, no. 26 (1983): 7512–6.
  • L. R. Domingo, M. Ríos-Gutiérrez, and P. Pérez, “A Molecular Electron Density Theory Study of the Reactivity of Tetrazines in Aza-Diels-Alder Reactions,” RSC Advances 10, no. 26 (2020): 15394–405.
  • J. I. García, J. A. Mayoral, and L. Salvatella, “Do Secondary Orbital Interactions Really Exist?,” Accounts of Chemical Research 33, no. 10 (2000): 658–64.
  • L. R. Domingo, M. Arnó, and J. Andrés, “Influence of Reactant Polarity on the Course of the Inverse-Electron-Demand Diels-Alder Reaction. A DFT Study of Regio- and Stereoselectivity, Presence of Lewis Acid Catalyst, and Inclusion of Solvent Effects in the Reaction between Nitroethene and Substituted Ethenes,” The Journal of Organic Chemistry 64, no. 16 (1999): 5867–75.
  • L. R. Domingo, M. Ríos-Gutiérrez, and P. Pérez, “Unveiling the Chemistry of Higher-Order Cycloaddition Reactions within the Molecular Electron Density Theory,” Chemistry 4, no. 3 (2022): 735–52.
  • L. R. Domingo, M. Ríos-Gutiérrez, and P. Pérez, “How Does the Global Electron Density Transfer Diminish Activation Energies in Polar Cycloaddition Reactions? A Molecular Electron Density Theory Study,” Tetrahedron 73, no. 13 (2017): 1718–24.
  • J. Soto-Delgado, L. R. Domingo, and R. Contreras, “Understanding the Influence of Lewis Acid in the Regioselectivity of the Diels-Alder Reactions of 2-Methoxy-5-Methyl-1,4-Benzoquinone. A DFT Study,” Journal of Molecular Structure: Theochem 902, no. 1-3 (2009): 103–8.
  • M. G. Evans, and M. Polanyi, “Some Applications of the Transition State Method to the Calculation of Reaction Velocities, Especially in Solution,” Transactions of the Faraday Society 31 (1935): 875–94.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.