Weak C–H···O and Dipole–Dipole Interactions as Driving Forces in Crystals of Fluorosubstituted Phenylboronic Catechol Esters

Izabela Madura , Karolina Czerwińska , Michał Jakubczyk , Alicja Pawełko , Agnieszka Adamczyk-Woźniak , Andrzej Sporzyński

Abstract

The analysis of weak interactions in crystals of a series of fluorosubstituted phenylboronic catechol esters (fphb) supported by Hirshfeld surface analysis is presented. The influence of the number and positions of fluorine atoms on the molecular structure is discussed and compared with results of the DFT calculations for isolated molecules. The molecular symmetry breaking caused by the intermolecular interactions was detected. The substantial differentiation of the dipole moments generated by fluorine substitution and its consequence on molecular packing are analyzed. The presence of ortho-fluoro substituents was found to enhance the proton acceptor character of oxygen atoms. Consequently, the C–H···O hydrogen-bonded centrosymmetric dimer is the dominating motif for molecules with small dipole moments. Otherwise, the antiparallel dipole–dipole interactions are responsible for the supramolecular architecture.
Author Izabela Madura (FC / CICSST)
Izabela Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Karolina Czerwińska (FC / CICSST)
Karolina Czerwińska,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Michał Jakubczyk (FC / DPC)
Michał Jakubczyk,,
- Department Of Physical Chemistry
, Alicja Pawełko (FC / DPC)
Alicja Pawełko,,
- Department Of Physical Chemistry
, Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
Journal seriesCrystal Growth and Design, ISSN 1528-7483
Issue year2013
Vol13
No12
Pages5344-5352
Publication size in sheets0.5
ASJC Classification3104 Condensed Matter Physics; 2500 General Materials Science; 1600 General Chemistry
DOIDOI:10.1021/cg4012026
URL http://pubs.acs.org/doi/abs/10.1021/cg4012026
Languageen angielski
File
cg4012026.pdf 4.02 MB
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 40.0, 31-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 31-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 22; WoS Citations = 20; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 1.441; WoS Impact Factor: 2013 = 4.558 (2) - 2013=4.727 (5)
Citation count*13 (2016-06-01)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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