The Close Interaction of a C-F Bond with an Amide Carbonyl: Crystallographic and Spectroscopic Characterization.
Amides
Fluorine
Non-Covalent Interactions
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
22 08 2022
22 08 2022
Historique:
received:
30
05
2022
pubmed:
19
6
2022
medline:
19
8
2022
entrez:
18
6
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 35716396
doi: 10.1002/anie.202207966
pmc: PMC9544880
doi:
Substances chimiques
Amides
0
Types de publication
Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202207966Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
J Org Chem. 2018 Oct 5;83(19):11586-11594
pubmed: 30180581
Phys Chem Chem Phys. 2015 Apr 21;17(15):9596-612
pubmed: 25776003
Nucleic Acids Res. 2000 Jan 1;28(1):235-42
pubmed: 10592235
J Phys Chem A. 2002 Mar 21;106(11):2623-2628
pubmed: 34959262
Angew Chem Int Ed Engl. 2022 Aug 22;61(34):e202207966
pubmed: 35716396
Chembiochem. 2004 May 3;5(5):637-43
pubmed: 15122635
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr;72(Pt 2):171-9
pubmed: 27048719
ChemMedChem. 2012 Feb 6;7(2):262-72
pubmed: 22262517
Nature. 2001 Nov 1;414(6859):43-8
pubmed: 11689936
Angew Chem Int Ed Engl. 2005 Mar 11;44(12):1788-805
pubmed: 15706577
Angew Chem Int Ed Engl. 2018 Feb 12;57(7):1924-1927
pubmed: 29316122
Nat Chem Biol. 2010 Aug;6(8):615-20
pubmed: 20622857
J Comput Chem. 2016 Jan 5;37(1):25-33
pubmed: 25903504
J Am Chem Soc. 1948 May;70(5):1913-6
pubmed: 18861813
Angew Chem Int Ed Engl. 2003 Jun 6;42(22):2507-11
pubmed: 12800172
Angew Chem Int Ed Engl. 2007;46(43):8270-3
pubmed: 17899581
Angew Chem Int Ed Engl. 2018 Mar 5;57(11):2758-2766
pubmed: 29141116
Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5056-9
pubmed: 15384111
J Am Chem Soc. 2015 Mar 25;137(11):3811-26
pubmed: 25714789
Drug Metab Rev. 1994;26(3):605-43
pubmed: 7924905
Acc Chem Res. 2000 Dec;33(12):849-58
pubmed: 11123884
Science. 2013 Apr 5;340(6128):57-60
pubmed: 23559245