SYNTHESIS AND THEORETICAL STUDY OF 4-ACETYL-5-(2-NAPHTYL)-2,3-DIHYDRO-2,3-FURANDIONE WITH SOME NITROGENOUS NUCLEOPHILES

Yıl 2016, Cilt: 12 Sayı: 2, 24 - 25, 01.08.2016

Murat Saracoglu Fatma Kandemirli Ayhan Özalp Zülbiye Kökbudak

Öz

The 2,4-dioxopentanoic acid derivatives (3d-f) were obtained from the reaction of 4-
acetyl-5-(1-naphthyl)furan-2,3-dione (1) with various nitrogenous nucleophiles (2d-f). The structures
of these newly synthesized compounds (3d-f) were determined from the FT-IR, 1H and 13C NMR
spectroscopic data and elemental analyses. Theoretical Study of derivatives of (3Z)-3-{2-naphthyl[2-
(4-nitrophenyl)hydrazino]methylene}-2,4-dioxopentanoic acid (3d-f) were carried out by using
DFT/B3LYP method with basis set of the 6-311G(d,p) in order to find molecular properties by
Gaussian 03 program [1](see Schemes 1and 2). According to EHOMO and softness values; electronic
give trends for investigated molecules can be written as: 3f>3d>3e.The EHOMO and EHOMO energy gap
of a measure of stability. Additionally, according to EHOMO and EHOMO energy gap; stability give
trends for investigated molecules can be written as: 3e>3d>3f.

Anahtar Kelimeler

Furan-2, 3-dione, Nitrogenous Nucleophiles, 2, 4-dioxopentanoic Acid, Quantum Chemical Calculations