Synthesis, crystal structure and theoretical studies of a Schiff base 2-[4-hydroxy benzylidene]-amino naphthalene

The molecular structure of a new Schiff base, 2-[4-hydroxy benzylidene]-amino naphthalene (HBAN) has been examined by HF and B3LYP/6-311++G(d,p) calculations. The X-ray structure was determined in order to establish the conformation of the molecule. The compound, C17H13NO, crystallizes in the orthorhombic, P2(1)2(1)2(1) space group with the cell dimension, a = 6.2867(2), b = 10.2108(3), c = 19.2950(6) angstrom, alpha = beta = gamma = 90 degrees and z = 4. The asymmetric unit contains a molecule of a Schiff base. A strong intermolecular O-H center dot center dot center dot N and a weak C-H center dot O hydrogen bonds stabilized the crystal structure. The vibrational spectra of HBAN have been calculated using density functional theoretical computation and compared with the experimental. The study is extended to the HOMO-LUMO analysis to calculate the energy gap (Delta), Ionization potential (I), Electron Affinity (A), Global Hardness (eta), Chemical Potential (mu) and Global Electrophilicity (w). The calculated HOMO and LUMO energy reveals that the charge transfer occurs within the molecule. (C) 2014 Elsevier B.V. All rights reserved.