Theoretical and X-ray studies on the cyclization of 1-phenyl-5-(3-aryltriaz-1-en-1-yl)‎- 1H-pyrazole-4-carbonitriles and 2-amino-3-(3-aryltriaz-1-en-1-yl)‎maleonitriles : a comparison study

الملخص EN

he present work investigates attempts to cyclize 1-phenyl-5-(3-aryltriaz-1-en-1-yl)-1Hpyrazole-4-carbonitriles to the desired pyrazolo[3,4-d] [1,2,3] triazinimine derivatives.

The cyclizations were unfruitful, and a density functional theory study was performed.

This revealed that 1-phenyl-5-(3-aryltriaz-1-en-1-yl)-1H-pyrazole-4-carbonitriles are more stable than the targeted pyrazolo[3,4-d][1,2,3]triazinimine derivatives, indicating that their cyclization is thermodynamically disfavoured; the reactant 8c is more stable than the predicted six-membered ring products 9c by 5 kJ/mol.

The effect of isomerization of the methoxy-phenyl group in the self-assembly of 8c and 8d in the crystalline lattice was investigated.

The intermolecular forces in the solid-state were analyzed for the two structural isomers 8c and 8d using calculated Hirsh Feld surface; the analysis indicates that the intermolecular forces are stronger in 8c than 8d and hence 8c is denser than 8d by 0.071g/mL.