title: Synthesis, structural characterization and theoretical approach of 3-(2,6-dichlorobenzyl)-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine.
abstract: 3-(2,6-Dichlorobenzyl)-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (DNOI) was synthesized and characterized by X-ray diffraction, FT-IR, FT-Raman and UV-Vis spectra. The X-ray diffraction study showed that DNOI has a one dimensional configuration, due to the intermolecular C9H⋯O1 and N4H⋯O2 hydrogen bonds. The benzene ring and the oxadiazine rings are tilted with respect to each other by 63.07° (C3N1C5C6). Vibrational spectra and electronic spectra measurements were made for the compound. Optimized geometrical structure and harmonic vibrational frequencies were computed with DFT (B3LYP, B3P86, and M062X) methods using 6-311++G(d,p) basis set. Assignments of the observed spectra were proposed. The equilibrium geometries computed by all of the methods were compared with X-ray diffraction results. The absorption spectra of the title compound were computed both in gas phase and in CH3OH solution using TD-B3LYP/6-311++G(d,p) and PCM-B3LYP/6-311++G(d,p) approaches, respectively. The calculated results provide a good description of positions of the bands maxima in the observed electronic spectrum. Temperature dependence of thermodynamic parameters in the range of 100-1000K were determined, entropy, heat capacity and enthalpy changes were increasing with temperature increasing, while for Gibbs free energy is decreasing with temperature increasing. The bond orbital occupancies, contribution from parent natural bond orbital (NBO), the natural atomic hybrids was calculated and discussed.
authors.affiliation: School of Chemical Engineering, Ningxia University, Ningxia 210094, PR China; Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China.
authors.forename: Haiwei
authors.initials: H
authors.lastname: Ni
authors.affiliation: Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China. Electronic address: yuzhang@hytc.edu.cn.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China.
authors.forename: Fang
authors.initials: F
authors.lastname: Zhang
authors.affiliation: Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China.
authors.forename: Jianying
authors.initials: J
authors.lastname: Zhao
authors.affiliation: Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China.
authors.forename: Liubi
authors.initials: L
authors.lastname: Wu
authors.affiliation: Huaian Key Laboratory for Photoelectric Conversion and Energy Storage Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China; Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, Jiangsu, PR China.
authors.forename: Xiaozhong
authors.initials: X
authors.lastname: Chu
mesh_terms: D018360:Crystallography, X-Ray; D019281:Dimerization; D004583:Electrons; D006860:Hydrogen Bonding; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013059:Spectrum Analysis, Raman; D055672:Static Electricity; D013816:Thermodynamics; D014732:Vibration
chemical_list: D007097:Imines; D010078:Oxazines
keywords: 3-(2,6-Dichlorobenzyl)-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (DNOI); Density functional theory (DFT); Electronic spectra; NBO; Vibrational spectra