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Issue 8, 2009
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The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

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Abstract

The synthesis and single crystal X-ray diffraction structures of five 2,6-disubstituted N-arylthioamides, viz.2,6-difluorophenylthioamide (1), 2,6-dichlorophenylthioamide (2), 2,6-dibromophenylthioamide (3), 2,6-dimethylphenylthioamide (4) and 2-chloro-6-methylphenylthioamide (5), are reported. The primary hydrogen-bonding motif consists of 1-D ribbons of molecules connected by N–H⋯S[double bond, length as m-dash]C hydrogen bonds and weak C–H⋯S[double bond, length as m-dash]C interactions. All five N-arylthioamide molecules adopt the cis conformation in the solid state, defined as the conformation where the amine proton is on the same side as the sulfur atom. The chains and ribbons of the five compounds feature a variety of weak intermolecular interactions, including C–H⋯S, C–X⋯π and π⋯π interactions.

Graphical abstract: The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

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Publication details

The article was received on 24 Nov 2008, accepted on 31 Mar 2009 and first published on 27 Apr 2009


Article type: Paper
DOI: 10.1039/B820944H
Citation: CrystEngComm, 2009,11, 1658-1665
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    The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

    B. Omondi, A. Lemmerer, M. A. Fernandes, D. C. Levendis and M. Layh, CrystEngComm, 2009, 11, 1658
    DOI: 10.1039/B820944H

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