Understanding the Reactivity, Selectivity, and Deactivation of Frustrated Lewis Pairs for Semihydrogenation of Acetylene

Ye, Jingyun; McEwen, Megan

doi:10.1021/acs.jpcc.2c05912

Understanding the Reactivity, Selectivity, and Deactivation of Frustrated Lewis Pairs for Semihydrogenation of Acetylene

Journal Article · Wed Oct 26 00:00:00 EDT 2022 · Journal of Physical Chemistry. C

DOI:https://doi.org/10.1021/acs.jpcc.2c05912· OSTI ID:2310971

^[1]; McEwen, Megan ^[2]

Duquesne University, Pittsburgh, PA (United States); Clarkson University, Potsdam, NY (United States); Duquesne University
Clarkson University, Potsdam, NY (United States)

A good catalyst for semihydrogenation of alkynes must preclude both over-hydrogenation of alkene to alkane and isomerization to the other alkene isomer. In addition, it should balance the trade-off between selectivity and activity. In 2013, the Repo and Pápai groups reported a frustrated Lewis pair (FLP) (1-NMe₂-2-B(C₆F₅)₂-C₆H₄), 1, which is a metal-free catalyst and for the first time shows excellent reactivity for the hydrogenation of internal alkynes. However, it is unreactive for terminal alkynes. In this work, we have designed 13 FLPs, a–m, based on 1 by varying the Lewis base site with N and P and the Lewis acid site with B, Al, Ga, and In and replacing pentafluorophenyl with 1,3,5-trifluorophenyl, phenyl, or trifluoromethyl. We apply density functional theory to study the activity, selectivity, and deactivation of FLP 1-m for acetylene semihydrogenation. The catalytic cycle consists of three steps: (1) alkyne insertion, (2) H₂ heterolysis, and (3) intramolecular protonation. We found the activity does not change much by the modification of bulky ligands, while it decreases with the direct replacement of LA and LB sites. The overall activity depends on steps 1 and 3, which are, respectively, positively and negatively linear correlated with the charge of the Lewis acid site. Most of the FLPs in this work show comparable or better selectivity for semihydrogenation of acetylene than 1. FLP deactivation is due to the strong binding of acetylene and the elimination of electron-withdrawing bulky ligands at the preactivated catalyst rather than at activated catalysts. Furthermore, taking the selectivity and stability of FLPs into account, we predict d and k are potentially active for terminal alkynes.

View Accepted Manuscript (DOE)

Research Organization:: Duquesne University, Pittsburgh, PA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: SC0008688

OSTI ID:: 2310971

Journal Information:: Journal of Physical Chemistry. C, Journal Name: Journal of Physical Chemistry. C Journal Issue: 44 Vol. 126; ISSN 1932-7447

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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