Unveiling the Different Reactivity of Bent and Linear Three-Atom-Components Participating in [3 + 2] Cycloaddition Reactions

References (37)

1. 1 Moss, 1995, Glossary of class names of organic compounds and reactivity intermediates based on structure [DOI]
2. 2 Carruthers, W. (1990). Cycloaddition Reactions in Organic Synthesis, Pergamon.
3. 3 Padwa, A. (1984). 1,3-Dipolar Cycloaddition Chemistry, Wileynterscience.
4. 4 Domingo, L.R. (2016). Molecular electron density theory: A modern view of reactivity in organic chemistry. Molecules, 21. [DOI]
5. 5 Ríos-Gutiérrez, M., and Domingo, L.R. (2019). Unravelling the mysteries of the [3 + 2] cycloaddition reactions. Eur. J. Org. Chem., 267–282. [DOI]
6. 6 Domingo, 2009, Understanding the mechanism of polar Diels–Alder reactions [DOI]
7. 7 Domingo, 2014, A new C-C bond formation model based on the quantum chemical topology of electron density [DOI]
8. 8 Domingo, 2017, How does the global electron density transfer diminish activation energies in polar cycloaddition reactions? A Molecular Electron Density Theory study [DOI]
9. 9 Domingo, 2020, A Molecular Electron Density Theory Study of the Reactivity of Tetrazines in Aza-Diels-Alder Reactions [DOI]
10. 10 Domingo, L.R., Kula, K., and Ríos-Gutiérrez, M. (2020). Unveiling the Reactivity of Cyclic Azomethine Ylides in [3 + 2] Cycloaddition Reactions within the Molecular Electron Density Theory. Eur. J. Org. Chem., 5938–5948. [DOI]
11. 11 Houk, 1995, Pericyclic reaction transition states: Passions and punctilios, 1935–1995 [DOI]
12. 12 Sustmann, 1972, Substituent Effects in 1,3-Dipolar Cycloadditions of Phenyl Azid [DOI]
13. 13 Domingo, 2018, The Mysticism of Pericyclic Reactions: A Contemporary Rationalisation of Organic Reactivity Based on Electron Density Analysis [DOI]
14. 14 Zhao, 2004, Hybrid Meta Density Functional Theory Methods for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions:  The MPW1B95 and MPWB1K Models and Comparative Assessments for Hydrogen Bonding and van der Waals Interactions [DOI]
15. 15 Hehre, M.J., Radom, L., Schleyer, P.v.R., and Pople, J. (1986). Ab Initio Molecular Orbital Theory, Wiley.
16. 16 Schlegel, 1982, Optimization of equilibrium geometries and transition structures [DOI]
17. 17 Yarkony, D.R. (1994). Modern Electronic Structure Theory, World Scientific Publishing. [DOI]
18. 18 Fukui, 1970, Formulation of the reaction coordinate [DOI]
19. 19 Schlegel, 1990, Reaction path following in mass-weighted internal coordinates [DOI]
20. 20 Schlegel, 1991, Improved algorithms for reaction path following: Higher-order implicit algorithms [DOI]
21. 21 Becke, 1990, A simple measure of electron localization in atomic and molecular-systems [DOI]
22. 22 Reed, 1985, Natural population analysis [DOI]
23. 23 Reed, 1988, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint [DOI]
24. 24 Parr, R.G., and Yang, W. (1989). Density Functional Theory of Atoms and Molecules, Oxford University Press.
25. 25 Domingo, L.R., Ríos-Gutiérrez, M., and Pérez, P. (2016). Applications of the conceptual density functional indices to organic chemistry reactivity. Molecules, 21. [DOI]
26. 26 Parr, 1999, Electrophilicity index [DOI]
27. 27 Parr, 1983, Absolute hardness: Companion parameter to absolute electronegativity [DOI]
28. 28 Domingo, 2008, Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study [DOI]
29. 29 Kohn, 1965, Self-consistent equations including exchange and correlation effects [DOI]
30. 30 Domingo, 2013, Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions [DOI]
31. 31 Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Fox, D.J. (2016). Gaussian 16, Gaussian, Inc.. Revision, A.03.
32. 32 Noury, 1999, Computational tools for the electron localization function topological analysis [DOI]
33. 33 Dennington, R., Keith, T.A., and Millam, J.M. (2016). Gauss View, Semichem Inc.. Version 6.0.
34. 34 Huisgen, 1961, 1,3-Dipolar Cycloadditions
35. 35 Chamorro, 2020, A close look to the oxaphosphetane formation along the Wittig reaction: A [2 + 2] cycloaddition? [DOI]
36. 36 Aurell, 2004, A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes [DOI]
37. 37 Hammond, 1955, A Correlation of Reaction Rates [DOI]

Cited by 32

Showing 16 of 32 known citations — external sources report more than can currently be individually listed.

Related research

• A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
• Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
• Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
• Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
• Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage