Investigation of the IntraMolecular Hydrogen Bonding in Halo, Methoxy, and Cyano-Malonealdehyde Derivatives

Subject Areas :

Hadi Zare yousefkhani ^{1 *} , mohammad vakili ² , vahidreza darugar ³

1 - Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
2 - Ferdowsi University of Mashhad, Department of Chemistry, Iran
3 - Department of Chemistry, Ferdowsi University of Mashhad, P.O.Box: 9177948974, Mashhad, Iran

Received: 2019-06-25 Accepted : 2019-10-11 Published : 2019-11-22

Keywords: OH stretching frequency, density functional theory, atom in molecule, natural molecular orbital theory, OH chemical shift, Intramolecular hydrogen bonding,

Abstract :

Intramolecular hydrogen bonding (IHB) of Malonaldehyde, as the simplest resonance-assisted hydrogen bond system in symmetric O–H…O class, and its halo derivatives (F, Cl, and Br), methoxy and cyano have been studied at the DFT-B3LYP/6-311++G∗∗ level of theory. We also performed the topological, structural, NBO, and spectroscopy parameters at the same level for them. Good linear correlation between IHB energies based on, Spinoza equation and structural parameters such as hydrogen bond length, covalent bond length, distance of two oxygen atom, hydrogen bond angle, topological parameters including Density and Laplacian at the critical points of the hydrogen bond and the chelated-ring and NBO parameters, including the wiberg of hydrogen bond and hyper conjugative interaction energy of lp(O) → σ∗(O–H), as well as Frequencies of the O–H stretching and bending, and chemical shift of bridged hydrogen in gas phase and solution were obtained.