Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: Comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts

doi:10.1016/j.molstruc.2011.08.054

淡江大學機構典藏 > 理學院 > 化學學系暨研究所 > 期刊論文 > Item 987654321/98705

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题名:	Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: Comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts
作者:	Yeh, Pao-Ling;Tai, Chin-Kuen;Shih, Tzenge-Lien;Hsiao, Hui-Ling;Wang, Bo-Cheng
贡献者:	淡江大學化學學系
关键词:	Conformational analysis;NMR calculation;Trihydroxyazepane
日期:	2012-06-27
上传时间:	2014-09-15 16:32:56 (UTC+8)
出版者:	Elsevier BV
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.
關聯:	Journal of Molecular Structure 1018, p.64–71
DOI:	10.1016/j.molstruc.2011.08.054
显示于类别:	[化學學系暨研究所] 期刊論文 [應用科學博士班] 期刊論文

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