Wydział Chemii

Anna Kwiecień

Maciej Barys

Zbigniew Ciunik

2014

Molecules

19

11160-11177

10.3390/molecules190811160

Naukowa

Angielski

Artykuł

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.

stable hemiaminal, stable intermediate, heteroatom hyperconjugation, crystal structure, 4-amino-1,2,4-triazole, formylbenzonitrile

CC-BY

http://dx.doi.org/10.3390/molecules190811160

http://www.mdpi.com/journal/metals