Intramolecular Hydrogen Bonding of (E)-N'-(n-Fluoro-2-hydroxybenzylidene) Nicotinohydrazide: A DFT study

Subject Areas :

Zainab Moosavi-Tekyeh ¹ (Assistant Professor, Chemistry Department, Shahrood University of Technology, Shahrood, Iran)

Received: 2017-10-12 Accepted : 2017-12-26 Published : 2017-11-22

Keywords: natural bond orbital analysis, density functional theory, (E)-N&#039, -(n-Fluoro-2-hydroxybenzylidene) nicotinohydrazide, Atoms in molecule theory, Intramolecular hydrogen bonding,

Abstract :

The nature of intramolecular hydrogen bonding (IHB) in (E)-N'-(n-Fluoro-2-hydroxybenzylidene) nicotinohydrazide (nF) compounds have been investigated at B3LYP/6-311++G** level of theory by using density functional theory (DFT) calculations. Then the parameters related to hydrogen bonding for O-H···N fragment in nF compounds compared with the corresponding parameters in (2-hydroxybenzylidene) nicotinohydrazide (2HBNH). The results of OH- vibrational frequencies, chemical shift and some geometrical parameters support a stronger intramolecular hydrogen bond for 4F compound (which F atom is in the para position with respect to the imine group) than 2HBNH. The geometrical and vibrational results were explained by considering the calculated electron density properties in AIM analysis and the natural charge of atoms and second order interaction energy of orbitals in NBO method.