Journal Article

PUBDB-2021-00778

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Do docking sites persist upon fluorination? The didamantyl ether-aromatics challenge for rotational spectroscopy and theory

Moreno, M. M. Q. ; Pinacho Morante, P.Extern* ; Perez Cuadrado, C.CFEL*DESY* ; Sekutor, M. ; Schreiner, P. R. ; Schnell, M. (Corresponding author)CFEL*DESY*

2021
Wiley-VCH Weinheim

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Please use a persistent id in citations: doi:10.1002/chem.202100078  doi:10.3204/PUBDB-2021-00778

Abstract: Fluorinated derivatives of biological molecules have proved to be highly efficient at modifying the biological activity of a given protein through changes in the stability and the kind of docking interactions. These interactions can be hindered or facilitated based on the hydrophilic/hydrophobic character of a particular protein region. Diadamantyl ether (C$_{20}$H$_{30}$O) possesses both kinds of docking sites, serving as a good template to model these important contacts with aromatic fluorinated counterparts. We report here an experimental study on the structures of several complexes between diadamantyl ether and benzene as well as a series of fluorinated benzenes to analyze the effect of H → F substitution on the interaction and structure of the resulting molecular clusters using rotational spectroscopy. All experimentally observed complexes are largely dominated by London dispersion interactions with the hydrogen‐terminated surface areas of diadamantyl ether. Already single substitution of one hydrogen atom with fluorine changes the preferred docking site of the complexes. However, the overall contributions of the different intermolecular interactions are similar for the different complexes, contrary to previous studies focusing on the difference in interactions using fluorinated and non‐fluorinated molecules.

Note: Onlinefirst

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Contributing Institute(s):

1. Spectroscopy of molecular processes (FS-SMP)
2. MPSD (CFEL-SDCCM)

Research Program(s):

1. 631 - Matter – Dynamics, Mechanisms and Control (POF4-631) (POF4-631)
2. DFG project 271359857 - Intra- und untermolekulare Dispersionskräfte: Beiträge zum Verständnis von Komplexbildung, Aggregation und dem Effekt der Solvatisierung mit Hilfe eines bottom-up Ansatzes (271359857) (271359857)

Experiment(s):

1. No specific instrument

Appears in the scientific report 2021

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Database coverage:
; ; ; Chemical Reactions ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; DEAL Wiley ; Ebsco Academic Search ; Essential Science Indicators ; IF >= 5 ; Index Chemicus ; JCR ; Nationallizenz ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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