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Can the −CF ₃ Group Act as a Tight, Well-Defined Hydrogen Bond Acceptor? A Clear Crystallographic CF ₂ –F···H–N ⁺ Interaction Says Yes

https://doi.org/10.1021/acs.joc.4c00873

Wang, Muyuan; Garrison, Nathaniel; Nguyen, Phuong Minh; Prasad, Aarush; Wang, Yuang; Kwon, Hyeok-Kyu; Kim, Gina; Siegler, Maxime A; Lectka, Thomas (July 2024, The Journal of Organic Chemistry)

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How Do Face-to-Face Stacked Aromatic Rings Activate Each Other to Electrophilic Aromatic Substitution?

https://doi.org/10.1021/acs.orglett.3c01401

Kazim, Muhammad; Wang, Muyuan; Vemulapalli, Srini; Nguyen, Phuong Minh; Wang, Yuang; Siegler, Maxime A.; Dudding, Travis; Lectka, Thomas (June 2023, Organic Letters)

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Competition between C–C and C–H Bond Fluorination: A Continuum of Electron Transfer and Hydrogen Atom Transfer Mechanisms

https://doi.org/10.1021/jacs.3c06477

Wang, Muyuan; Rowshanpour, Rozhin; Guan, Liangyu; Ruskin, Jonah; Nguyen, Phuong Minh; Wang, Yuang; Zhang, Qinze Arthur; Liu, Ran; Ling, Bill; Woltornist, Ryan; et al (October 2023, Journal of the American Chemical Society)

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The Close Interaction of a C−F Bond with an Amide Carbonyl: Crystallographic and Spectroscopic Characterization

https://doi.org/10.1002/anie.202207966

Harry, Stefan Andrew; Kazim, Muhammad; Nguyen, Phuong Minh; Zhu, Andrea; Xiang, Michael Richard; Catazaro, Jonathan; Siegler, Maxime; Lectka, Thomas (July 2022, Angewandte Chemie International Edition)

Abstract The putative interaction of a C−F bond with an amide carbonyl has been an intriguing topic of interest in this century for reasons spanning basic physical organic chemistry to biochemistry. However, to date, there exist no examples of a close, well‐defined interaction in which its unique aspects can be identified and exploited. Herein, we finally present an engineered system possessing an exceptionally tight C−F‐amide interaction, allowing us to obtain spectroscopic, crystallographic, and kinetic details of a distinctive, biochemically relevant chemical system for the first time. In turn, we also explore Lewis acid coordination, C−F bond promotion of amide isomerization, enantiomerization, and ion protonation processes.
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