XRD, FTIR, ¹H NMR, ¹³C NMR and UV spectroscopic and computational studies of [3-(hydroxyimino)butan-2-ylidene]furan-2′-carbohydrazide

ABSTRACT

[3-(hydroxyimino)butan-2-ylidene]furan-2′-carbohydrazide (1) has been synthesized and characterized by IR, 1H NMR, 13C NMR, UV/vis and X-ray diffraction. In addition to the experimental studies, the optimized structure, vibrational parameters, chemical shifts, thermodynamic properties, ionization energy, electron affinity, electronegativity, global chemical hardness and chemical softness of the molecule have been investigated by using DFT with B3LYP/6.311G(d, p) and PBEPBE/6.311G(d, p) basis sets. HOMO and LUMO energies were calculated by TD-DFT approach in two different solvents. The experimental results of the compound have been compared with theoretical results and it is found to show good agreement with calculated values.

KEYWORDS:

• Single crystal
• Hydrazone
• Furan
• Oxime
• DFT
• Energy gap

Supplementary data

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No 1058076. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: [phone]; e-mail: [email protected] or www: http://www.ccdc.cam.ac.uk).

Supplementary Information

Besides experimental studies, harmonic vibrational frequencies, ¹³C and ¹H NMR, electrostatic potential map and thermodynamic parameters were calculated by using B3LYP/6--311G(d, p) and PBEPBE/6--311G(d, p). The results of harmonic vibrational frequencies are tabulated in S1. The theoretical ¹³C and ¹H chemical shift values (with respect to TMS) of the title compound in DMSO solvent are tabulated in S2. The thermodynamic parameters can be seen from S3. Electrostatic potential map calculated by using B3LYP/6--311G(d, p) of the compound can be seen from S4.

Acknowledgments

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the STOE IPDS-II diffractometer (purchased under Grant F.279 of the University Research Fund).