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Molecules 2014, 19(8), 11160-11177; doi:10.3390/molecules190811160

Stable Hemiaminals with a Cyano Group and a Triazole Ring

Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław 50-383, Poland
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Received: 17 June 2014 / Revised: 4 July 2014 / Accepted: 11 July 2014 / Published: 30 July 2014
(This article belongs to the Section Molecular Diversity)
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Abstract

Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results from both the 1,2,4-triazole moiety and electron withdrawing substituents on the phenyl ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess stereogenic centres on carbon and nitrogen atoms. The chirality of these centres is strongly correlated with the conformation of the molecules due to heteroatom hyperconjugation effects. View Full-Text
Keywords: stable hemiaminal; stable intermediate; heteroatom hyperconjugation; crystal structure; 4-amino-1,2,4-triazole; formylbenzonitrile stable hemiaminal; stable intermediate; heteroatom hyperconjugation; crystal structure; 4-amino-1,2,4-triazole; formylbenzonitrile
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Kwiecień, A.; Barys, M.; Ciunik, Z. Stable Hemiaminals with a Cyano Group and a Triazole Ring. Molecules 2014, 19, 11160-11177.

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