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Issue 11, 2012
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Investigation on the weak interactions assembling the crystal structures of Betti bases

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Abstract

The crystal structures of (S, S)-aminobenzylnaphthols, easily produced by a chromatography-free highly stereoselective Betti reaction, were investigated by means of single crystal X-ray diffraction analysis, and the main intra- and intermolecular interactions were described. The presence of a strong intramolecular hydrogen bond was confirmed, whereas the whole crystal building was found to be due mainly to other bondings, such as CH⋯O and CH⋯π interactions. As far as the last interactions were concerned, we observed many short distances from one hydrogen atom to an aryl plane, together with the appropriate geometric requirements for the assemblies. The observations suggest that these interactions can play a relevant role in the crystal building. The absence of similar short distance CH⋯π interactions in the crystal of a diastereomeric (R, S)-aminobenzylnaphthol could be a suggestion of the preferential crystallisation of the (S, S)-stereoisomer and, consequently, its prevalence as a product of the Betti reaction.

Graphical abstract: Investigation on the weak interactions assembling the crystal structures of Betti bases

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Publication details

The article was received on 29 Sep 2011, accepted on 09 Mar 2012 and first published on 23 Apr 2012


Article type: Paper
DOI: 10.1039/C2CE06295J
Citation: CrystEngComm, 2012,14, 3972-3981
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    Investigation on the weak interactions assembling the crystal structures of Betti bases

    C. Cardellicchio, M. A. M. Capozzi, A. Alvarez-Larena, J. F. Piniella and F. Capitelli, CrystEngComm, 2012, 14, 3972
    DOI: 10.1039/C2CE06295J

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