Synthesis, crystal structures, spectroscopic analysis and DFT calculations of 2-ethoxy-1-naphtaldehyde and (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline

• The titled compounds were studied with XRD, FT-IR and UV–Vis methods.
• Both Gaussian and Slater type orbitals have been used in DFT calculations.
• DFT calculations were performed for the complete analysis of each spectral band.
• NLO calculations reveal the nonlinear optical material characters of the compounds.
• Electrophilic attack regions were determined by Fukui functions.

(E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline has been synthesized and characterized by using single-crystal X-ray diffraction, FT-IR, UV–Visible spectroscopy and computational methods. By using the same techniques, also for the first time, the 2-ethoxy-1-naphtaldehyde has been characterized. The molecular geometries, intra- and inter-molecular interactions of the compounds have been found by using X-ray crystallography. Characteristic infrared bands and the electronic bands have been discovered by experimental and theoretical IR and UV–Vis. spectroscopy. The geometry optimizations and the calculations of IR frequencies have been performed by using the Gaussian type orbitals at Gaussian 09W and the Slater type orbitals at ADF2009.01 software. In addition, the Fukui functions have been calculated to reveal active sites of the compounds. Furthermore, non-linear optical properties and thermodynamic correlation functions have been theoretically found for a further study of the titled compounds.

Molecular electrostatic potential maps and dipole moment vectors of the studied compounds (Left: 2ethoxy1naphtaldehyde, Right: (E)-N-((2-ethoxynaphthalen-1-yl)methylene)-3-methylaniline).Figure optionsDownload as PowerPoint slide