Rodríguez, Humberto A.Bickelhaupt, F. MatthiasFernández López, Israel2024-06-242024-06-242023H. A. Rodríguez, F. M. Bickelhaupt, I. Fernández, ChemPhysChem 2023, 24, e202300379.1439-423510.1002/cphc.202300379https://hdl.handle.net/20.500.14352/105195The Bürgi-Dunitz (BD) angle plays a pivotal role in organic chemistry to rationalize the nucleophilic addition to carbonyl groups. Yet, the origin of the obtuse trajectory of the nucleophile remains incompletely understood. Herein, we quantify the importance of the underlying physical factors quantum chemically. The obtuse BD angle appears to originate from the concerted action of a reduced Pauli repulsion between the nucleophile HOMO and carbonyl π bond, a more stabilizing HOMO-π*-LUMO(C=O) interaction, as well as a more favorable electrostatic attraction.engAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/journal article1439-7641https://doi.org/10.1002/cphc.202300379https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cphc.202300379open access547Bürgi-Dunitz angleNucleophilic additionCarbonylPauli repulsionDensity functional calculationsQuímica orgánica (Química)2306 Química Orgánica