Abstract
New N-methyl-C-2,4,6-trimethylphenylnitrone has been synthesized and characterized using FTIR, NMR, UV–Vis, high resolution mass spectrometry and X-ray diffraction. The relative stability and percentage population of its two possible isomers (E and Z) have been calculated using the B3LYP/6-311++G(d,p). [Display omitted]
•New N-methyl-C-2,4,6-trimethylphenylnitrone has been synthesized.•Z-isomer is more stable than the E-one both in gas phase and in solution.•The IR, electronic and NMR spectra were studied experimentally and theoretically.•The studied nitrone has about five times higher NLO than urea.•NBO analysis indicates the presence of weak CH---O non-conventional interaction.
New N-methyl-C-2,4,6-trimethylphenylnitrone 1 has been synthesized starting from N-methylhydroxylamine and mesitaldehyde. The product was fully characterized using different spectroscopic techniques; FTIR, NMR, UV–Vis, high resolution mass spectrometry and X-ray diffraction. The relative stability and percent of population of its two possible isomers (E and Z) were calculated using the B3LYP/6-311++G(d,p) method in gas phase and in solution. In agreement with the X-ray results, it was found that Z-isomer is the most stable one in both gas phase and solution. The molecular geometry, vibrational frequencies, gauge-including atomic orbital (GIAO), and chemical shift values were also calculated using the same level of theory. The TD-DFT results of the studied nitrone predicted a π–π∗ transition band at 285.1nm (fosc=0.3543) in the gas phase. The rest of the spectral bands undergo either hyperchromic or hypsochromic shifts in the presence of solvent. Polarizability and HOMO–LUMO gap values were used to predict the nonlinear optical properties (NLO) of the studied compound. NBO analysis has been used to determine the most accurate Lewis structure of the studied molecule.