New insights into steric and electronic effects in a series of phosphine ligands from the perspective of local quantum similarity using the Fukui function

Abstract

The field of molecular quantum similarity (MQS) was introduced by Carbó-Dorca 30 years ago. MQS currently suffers from numerous bottlenecks, for example when studying similarities in chemical reactivity, because there is no clear guidance on the best methodology to follow. For this reason, we have revisited this topic here. Today’s search tools and methodologies have made an important contribution to studying steric and electronic effects in phosphine ligands (PR3). In this contribution, we propose a hybrid methodology joining (MQS) and chemical reactivity. Additionally, a chemical reactivity study using global and local reactivity descriptors was performed in the context of density functional theory (DFT). Phosphines are σ-donor and π-acceptor ligands, therefore reactivity descriptors allow us quantify the retrodonor process in terms of quantum similarity (QS). In this regard, new ways to characterize steric and electronic effects in phosphine ligands and their chemical bonds are presented in the QS context.

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Acknowledgments

Thanks to the Universidad de Talca [Centro de Bioinformática y Simulación molecular (CBSM)] for continuous support of this investigation, to Dr. Ramon Carbó-Dorca (Universidad de Girona, España) for the Topo-Geometrical Superposition Algorithm (TGSA) program, to the postdoctoral project No. 3150035 [FONDECYT (Fondo Nacional de Desarrollo Científico y Tecnológico), Chile] and finally thanks to Dr. Peter Politzer (associate editor) for his valuable comments.

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Correspondence to Alejandro Morales-Bayuelo.

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Morales-Bayuelo, A., Caballero, J. New insights into steric and electronic effects in a series of phosphine ligands from the perspective of local quantum similarity using the Fukui function. J Mol Model 21, 45 (2015). https://doi.org/10.1007/s00894-015-2600-x

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Keywords

  • Phosphine ligand
  • Molecular quantum similarity
  • Reactivity descriptor
  • Density functional theory