Publication Type Journal Article
Title Exploring the influence of steric hindrance and electronic nature of substituents in the supramolecular arrangements of 5-(substituted phenyl)-2-formylpyrroles
Authors Claudia A. Figueira Patrícia S. Lopes Clara S. B. Gomes Luis F. Veiros Pedro T. Gomes
Groups IOARC
Journal CRYSTENGCOMM
Year 2015
Month
Notice: Undefined index: in /afs/ist.utl.pt/groups/cqe/web/tmp/templates_c/77f86a5f762542dadf50c7f7fefa96acd45c2726_0.file.paper.tpl.html.php on line 163
Volume 17
Number 33
Pages 6406-6419
Abstract A family of 5-(substituted phenyl)-2-formylpyrrole compounds, exhibiting different electronic and steric features at the phenyl ring, was synthesised through the formylation reaction of the corresponding 2-(substituted phenyl) pyrrole precursors, using Vilsmeier-Haack acylation conditions. The products were obtained in moderate to high yields, being systematically characterised by NMR spectroscopy, elemental analysis and single crystal X-ray diffraction. The corresponding crystalline packings were discussed on the basis of three types of arrangements, leading to the formation of dimers, polymers or the newly observed tetramers, all of them essentially governed by strong N-H center dot center dot center dot O hydrogen bonding interactions. Important C-H center dot center dot center dot O, C-H center dot center dot center dot pi, pi center dot center dot center dot pi and, in the case of fluorinated compounds, C-H center dot center dot center dot F interactions also contributed to the growth of the three-dimensional crystalline network. DFT calculations helped to rationalise the relationship between the steric and electronic properties of the molecules and the basic units observed in the corresponding solid state structures.
DOI http://dx.doi.org/10.1039/c5ce00927h
ISBN
Publisher ROYAL SOC CHEMISTRY
Book Title
ISSN 1466-8033
EISSN
Conference Name
Bibtex ID ISI:000359270700019
Observations
Back to Publications List