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Citation: LIU Yan-Zhu, ZHANG Ling, LI Xia, LI Yong-Xiu. Comparison among the Spectral Properties ofMethyl Salicylate and Its Nitration Products by Iron (III) Nitrate[J]. Acta Physico-Chimica Sinica, ;2009, 25(10): 2118-2122. doi: 10.3866/PKU.WHXB20091005 shu

Comparison among the Spectral Properties ofMethyl Salicylate and Its Nitration Products by Iron (III) Nitrate

1.
Department of Chemistry, School of Science, Nanchang University, Nanchang 330031, P. R. China

Received Date: 6 May 2009
Available Online: 18 August 2009

Methyl 3-nitrosalicylate (3-MNS) and methyl 5-nitrosalicylate (5-MNS) were synthesized by a nitration reaction between methyl salicylate (MS) and iron (III) nitrate under reflux. 3-MNS and 5-MNS were characterized by infrared spectra (IR), proton nuclear magnetic resonance spectra (1H-NMR), electronic absorption spectra (UV-Vis), and photoluminescence (PL). The structures of 3-MNS and 5-MNS were fully optimized at the B3LYP/6-31G** level. The optimized results and nature bond orbital (NBO) analysis results were used to illustrate the red-shift of the O—H and C=O stretching vibrations in the IR, the lower field shift of the phenol hydroxyl proton chemical shift in 1H-NMR, and the bathochromic shift in the UV-Vis spectra of 3-MNS. Potential energy surfaces for the intramolecular proton transfer of ground (GSIPT) and excited (ESIPT) states of MS and 3-MNS were obtained and the Stokes-shift values for MS and 3-MNS were computed to be 8.4 ×103 and 8.9×103 cm -1 using CIS/6-31G**, respectively. All these results demonstrate that differences in intramolecular hydrogen bonding in MS, 3-MNS, and 5-MNS give rise to large differences in their spectral properties.
- Intramolecular hydrogen bond,
- Nitration,
- Methyl salicylate,
- B3LYP/6-31G**
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