Confirmed Mechanism for 1,8-Diaminonaphthalene and Ethyl Aroylpyrovate Derivatives Reaction, DFT/B3LYP, and Antimicrobial Activity of the Products

Table 1

DFT/B3LYP (3-21G) parameters over all proposed tautomers (12–18 and 21A–C).

The indexes	Compounds proposed
	12	13	14	15	16	17	18	21A	21B	21C
DFT (in the gas phase)	Method used
E (A.U.)	−1179.0538	−1179.0176	−1024.8445	−1024.8229	−1024.7594	−1102.9729	−1102.8973	−1250.7728	−1250.7425	−1250.7516
HOMO (ev)	−0.16943	−0.17047	−0.18788	−0.20387	−0.20432	−0.20184	−0.19332	−0.16835	−0.18688	−0.17179
LUMO (ev)	−0.06024	−0.04643	−0.07797	−0.07446	−0.07475	−0.07489	−0.07923	−0.08974	−0.05425	−0.08767
ΔEL-H (ev)	0.10919	0.12404	0.10991	0.12941	0.12957	0.12695	0.11409	0.07861	0.13263	0.08412
Dipole moment (debye)	5.0333	2.9408	2.4273	2.3373	6.1572	3.3955	4.8856	6.4436	3.3095	3.0171
Oscillator strength	0.0008	0.0001	0.0312	0.0250	0.1241	0.0032	0.0250	0.0009	0.0027	0.0190
DFT (in ethanol)	Method used
E (A.U.)	−1179.0712	−1179.0348	−1024.8601	−1024.8385	−1024.7798	−1102.9871	−1102.9147	−1250.7924	−1250.7603	−1250.7632
HOMO (ev)	−0.18124	−0.18105	−0.19124	−0.20708	−0.20530	−0.20738	−0.20142	−0.18347	−0.19622	−0.18512
LUMO (ev)	−0.06190	−0.05161	−0.08301	−0.08130	−0.08213	−0.08088	−0.08783	−0.08816	−0.06388	−0.08547
ΔEL-H (ev)	0.11934	0.12944	0.108139	0.12578	0.12317	0.1265	0.11359	0.09531	0.13234	0.09965
Dipole moment (debye)	6.2687	3.9833	2.9013	3.0273	8.6666	4.7047	6.8986	8.3543	4.2647	4.5073
Oscillator strength	0.0012	0.0002	0.0369	0.0211	0.5074	0.004	0.0377	0.0038	0.0032	0.0098