Synthesis, spectroscopic characterization and quantum chemical computational studies of (S)-N-benzyl-1-phenyl-5-(pyridin-2-yl)-pent-4-yn-2- amine
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2012
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Abstract
The synthesis and characterization of a novel compound (S)-N-benzyl-1- phenyl-5-(pyridin-2-yl)-pent-4-yn-2-amine (abbreviated as BPPPYA) was presented in this study. The spectroscopic properties of the compound were investigated by FT-IR, NMR and UV spectroscopy experimentally and theoretically. The molecular geometry and vibrational frequencies of the BPPPYA in the ground state were calculated by using density functional theory (DFT) B3LYP method invoking 6-311++G(d,p) basis set. The geometry of the BPPPYA was fully optimized, vibrational spectra were calculated and fundamental vibrations were assigned on the basis of the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method and PQS program. The results of the energy and oscillator strength calculated by time-dependent density functional theory (TD-DFT) and CIS approach complement with the experimental findings. Total and partial density of state (TDOS and PDOS) and also overlap population density of state (COOP or OPDOS) diagrams analysis were presented. The theoretical NMR chemical shifts (1H and 13C) complement with experimentally measured ones. The dipole moment, linear polarizability and first hyperpolarizability values were also computed. The linear polarizabilities and first hyper polarizabilities of the studied molecule indicate that the compound is a good candidate of nonlinear optical materials. The calculated vibrational wavenumbers, absorption wavelengths and chemical shifts showed the best agreement with the experimental results. © 2012 Elsevier B.V. All rights reserved.
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Amines , Benzyl Compounds , Electrons , Hardness , Magnetic Resonance Spectroscopy , Models, Chemical , Molecular Conformation , Nonlinear Dynamics , Optical Phenomena , Pyridines , Quantum Theory , Solvents , Spectrophotometry, Ultraviolet , Static Electricity , Thermodynamics , Vibration , Chemical shift , Nonlinear optics , Nuclear magnetic resonance , Organic compounds , Population statistics , Quantum chemistry , Quantum theory , Ultraviolet spectroscopy , (S) N benzyl 1 phenyl 5 (pyridin 2 yl) pent 4 yn 2 amine , (S)-N-benzyl-1-phenyl-5-(pyridin-2-yl)-pent-4-yn-2-amine , amine , benzyl derivative , pyridine derivative , solvent , Absorption wavelengths , B3LYP method , Basis sets , Computational studies , Density functional theories (DFT) , DFT , First hyperpolarizabilities , FT-IR , Fundamental vibrations , Molecular geometries , NMR chemical shifts , Non-linear optical material , Oscillator strengths , Partial density of state , Polarizabilities , Population densities , Quantum chemical , Scaled Quantum Mechanics , Spectroscopic characterization , Spectroscopic property , Time dependent density functional theory , Total energy distributions , UV , Vibrational modes , Vibrational wavenumbers , article , chemical model , chemistry , conformation , electron , hardness , light related phenomena , nonlinear system , nuclear magnetic resonance spectroscopy , quantum theory , static electricity , synthesis , thermodynamics , ultraviolet spectrophotometry , vibration , Density functional theory