Cover Feature: A Unified Framework for Understanding Nucleophilicity and Protophilicity in the SN2/E2 Competition (Chem. Eur. J. 67/2020)
Chemistry - A European Journal, vol. 26, pp. 15341
Abstract
The inherent competition between the bimolecular nucleophilic substitution (SN2) and base-induced elimination (E2) reactions is depicted in the cover image. This work reports a physically sound and intuitive model to elucidate why strong Lewis bases act as protophiles (E2), while weak Lewis bases behave as nucleophiles (SN2). The general concepts of “characteristic distortivity” and “transition state acidity” are developed, which will serve as the cornerstone for the rational design of novel reactions. More information can be found in the Full Paper by T. A. Hamlin, F. M. Bickelhaupt, et al. on page 15538.
Authors 5
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Affiliation as printed
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
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ETH Zurich · Vrije Universiteit Amsterdam · Laboratory of Physical Chemistry
Affiliation as printed
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Laboratory of Physical Chemistry ETH Zurich Vladimir-Prelog-Weg 2 8093 Zurich Switzerland
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Laboratory of Physical Chemistry ETH Zurich Vladimir-Prelog-Weg 2 8093 Zurich Switzerland
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Institució Catalana de Recerca i Estudis Avançats · Universitat de Girona
Affiliation as printed
ICREA Pg. Lluís Companys 23 08010 Barcelona Spain
IQCC & Dept. Química Universitat de Girona Campus Montilivi (Ciències) 17003 Girona Spain
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Trevor A. Hamlin corresponding
Affiliation as printed
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
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F. Matthias Bickelhaupt corresponding
Radboud University Nijmegen · Vrije Universiteit Amsterdam
Affiliation as printed
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands
Department of Theoretical Chemistry Amsterdam Institute of, Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale, Modeling (ACMM) Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands
Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands
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