Publication Type Journal Article
Title Effect of C-H center dot center dot center dot X interactions (X = O, S, pi) in the supramolecular arrangements of 3-ferrocenyl-methoxybenzo[b]thiophene isomers
Authors João Ferreira da Silva Andre P. Ferreira M. Matilde Marques Shrika G. Harjivan M.Fatima M.Piedade M. Teresa Duarte
Groups BioMol
Journal CRYSTENGCOMM
Year 2011
Month
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Volume 13
Number 5
Pages 1638-1645
Abstract Two regioisomers, 3-ferrocenyl-6-methoxybenzo[b]thiophene (IV) and 3-ferrocenyl-4-methoxybenzo[b]thiophene (V), were isolated after an acid-catalysed intramolecular electrophilic cyclisation of 1-ferrocenyl-2-[3-(methoxyphenyl)thio]ethanone. This paper analyses the effect of the different positioning of the methoxy group in the benzothiophene ring on the molecular and crystal structures of both molecules. In isomer IV this group is more exposed to interactions with adjacent molecules than in V; thus, while in IV the C-OMe-H center dot center dot center dot O-OMe intermolecular interactions determine the crystal packing, in V the overall assembly results from an interplay of the C-Cp-H center dot center dot center dot O-OMe, C-Cp-H center dot center dot center dot S and C-Cp-H/pi interactions. The supramolecular analysis provides an explanation for the spontaneous solid state separation of these regioisomers and their different physical properties, such as their melting points and their ability to interact with supports during chromatographic separations.
DOI http://dx.doi.org/10.1039/c0ce00434k
ISBN
Publisher
Book Title
ISSN 1466-8033
EISSN
Conference Name
Bibtex ID ISI:000287458500053
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