DFT calculations of the tautomerization and NW properties of 5-amino-7-(pyrrolidin-1-y1)-2,4,4-trimethy1-1,4-dihydro-1,6-naphthyridine-8-carbonitrile (APNC)

Amine-imine tautomerization in 5-amino-7-(pyrrolidin-1-y1)-2,4,4-trimethy1-1,4-dihydro-1,6-naphthyridine-8-carbonitrile (APNC) has been studied using the B3LYP, CAM-B3LYP and wB97XD with 6-311++G(d,p) basis set. Optimum molecular geometries, electronic properties, energetics and electronic densities of these systems have been discussed and compared with the available experimental data. Investigation reveals that one tautomer (the amine tautomer) dominates the gas phase. The photochromic properties of APNC and its two imine tautomers have been studied at the elected DFT-functionals and basis set. The interconversion Al to 12/13 is predicted to occur photochemically. The NLO properties were also evaluated and discussed. (C) 2017 Elsevier B.V. All rights reserved.