Base-Dependent Lewis Acidity in Substituted Boranes: Revisiting Intrinsic Acidity through DFT and Machine Learning
- 1Department of Chemistry and Material Science, School of chemical Engineering
- 2Aalto University
Abstract
The Lewis acidity of boranes is strongly influenced by the electronic nature of their substituents and is commonly assessed through interactions with representative Lewis bases. However, the extent to which the relative Lewis acidity ordering of substituted boranes depends on the identity of the interacting Lewis base has not been systematically investigated. In this work, Density Functional Theory (DFT) calculations combined with machine learning (ML) analysis were employed to quantify substituent effects and base dependence in borane–Lewis base interactions. A dataset comprising 816 trisubstituted boranes generated from 16 representative substituents was examined in interaction with five Lewis bases (H2O, NH3, C5H5N, P(CH3)3, and Cl−), yielding 3927 computed adduct formation free energies. The results show that electron-withdrawing substituents generally enhance, whereas electron-donating substituents attenuate, the Lewis acidity of boranes. However, the magnitude of these substituent effects depends on the identity of the interacting
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BibTeX
@misc{mahdian2026basedependent,
title = {{Base-Dependent Lewis Acidity in Substituted Boranes: Revisiting Intrinsic Acidity through DFT and Machine Learning}},
author = {Amir Mahdian and Kari Laasonen and Kaveh Farshadfar},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010041/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010041/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Base-Dependent Lewis Acidity in Substituted Boranes: Revisiting Intrinsic Acidity through DFT and Machine Learning
AU - Amir Mahdian
AU - Kari Laasonen
AU - Kaveh Farshadfar
PY - 2026
DA - 2026/10/07
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010041/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010041/v1
AB - The Lewis acidity of boranes is strongly influenced by the electronic nature of their substituents and is commonly assessed through interactions with representative Lewis bases. However, the extent to which the relative Lewis acidity ordering of substituted boranes depends on the identity of the interacting Lewis base has not been systematically investigated. In this work, Density Functional Theory (DFT) calculations combined with machine learning (ML) analysis were employed to quantify substituent effects and base dependence in borane–Lewis base interactions. A dataset comprising 816 trisubstituted boranes generated from 16 representative substituents was examined in interaction with five Lewis bases (H2O, NH3, C5H5N, P(CH3)3, and Cl−), yielding 3927 computed adduct formation free energies. The results show that electron-withdrawing substituents generally enhance, whereas electron-donating substituents attenuate, the Lewis acidity of boranes. However, the magnitude of these substituent effects depends on the identity of the interacting
ER -