Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: Comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts
學年 100
學期 2
出版（發表）日期 2012-06-01
作品名稱 Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: Comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts
作品名稱（其他語言）
著者 Yeh, Pao-Ling; Tai, Chin-Kuen; Shih, Tzenge-Lien; Hsiao, Hui-Ling; Wang, Bo-Cheng
單位 淡江大學化學學系
出版者 Amsterdam: Elsevier BV
著錄名稱、卷期、頁數 Journal of Molecular Structure 1018, pp.64–71
摘要 DFT/B3LYP/6-311++G(d,p) calculation of the relative stable conformations of (3R,4R,6S)-trihydroxyazepane are presented. The GIAO/DFT/OPBE, GIAO/DFT/B3LYP and GIAO/HF single point calculations with 6-311++G(d,p), 6-311+G(2d,p), cc-pVDZ and cc-pVTZ basis sets of (3R,4R,6S)-trihydroxyazepane were conducted to generate their 13C NMR chemical shifts. According to calculation results, 14 (3R,4R,6S)-trihydroxyazepane with optimized structure were generated. There were three conformers which contain the intramolecular hydrogen bonding exhibit a lowest electronic energies and TCN1(eq) was the most stable conformer than others. Boltzmann weighting factor analysis exhibits that TCN1(eq), TCN3(eq) and TCN5(eq) dominate a major contribution among the 14 conformers. The individual calculated NMR results of TCN1(eq), TCN3(eq) and TCN5(eq) represents a quite close correlation with experimental data. Moreover, the experimental 13C NMR chemical shifts gave only the average contribution of all conformers. In our investigation, the calculated 13C NMR chemical shifts of mixture (3R,4R,6S)-trihydroxyazepane exhibit a good agreement with the experimental NMR data. Calculated NMR results of mixture (3R,4R,6S)-trihydroxyazepane conformers display a remarkable MAE and RMS improvement over that of each individual conformer. A good calculation method and basis set choice to evaluate the theoretical chemical shifts for these conformers is HF/cc-pVTZ.
關鍵字 Conformational analysis; NMR calculation; Trihydroxyazepane
語言 en
ISSN 0022-2860
期刊性質 國外
收錄於 SCI
產學合作
通訊作者 Shih, Tzenge-Lien; Wang, Bo-Cheng
審稿制度 是
國別 NLD
公開徵稿
出版型式 紙本
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