系統識別號 | U0002-2007201115151900 |
---|---|
DOI | 10.6846/TKU.2011.00740 |
論文名稱(中文) | Trihydroxyazepanes的結構與13C化學 位移之理論計算研究 |
論文名稱(英文) | Theoretical Studies of Structures and 13C NMR Chemical Shifts for Trihydroxyazepanes |
第三語言論文名稱 | |
校院名稱 | 淡江大學 |
系所名稱(中文) | 化學學系博士班 |
系所名稱(英文) | Department of Chemistry |
外國學位學校名稱 | |
外國學位學院名稱 | |
外國學位研究所名稱 | |
學年度 | 99 |
學期 | 2 |
出版年 | 100 |
研究生(中文) | 葉寶玲 |
研究生(英文) | Pao-Ling Yeh |
學號 | 893170018 |
學位類別 | 博士 |
語言別 | 繁體中文 |
第二語言別 | |
口試日期 | 2011-06-28 |
論文頁數 | 195頁 |
口試委員 |
指導教授
-
王伯昌
委員 - 陳正隆 委員 - 江志強 委員 - 高惠春 委員 - 施增廉 委員 - 鄧金培 |
關鍵字(中) |
七圓環醣水解酵素抑制劑 幾何結構最佳化 化學位移 平均絕對誤差 |
關鍵字(英) |
conformational analysis NMR calculation trihydroxyazepane |
第三語言關鍵字 | |
學科別分類 | |
中文摘要 |
本論文係研究三種trihydroxyazepanes異構物之穩定構形,由於七圓環醣水解酵素抑制劑結構的易變性,所以可以藉由理論計算去預測可能的結構。幾何結構最佳化是使用Gaussian 03軟體中的DFT/B3LYP/6-311++G(d,p),得到每種異構物各有28個構形,其中能量較低為相對穩定的構形,再以Gibbs自由能算出28個構形之Boltzmann分佈。接著針對三種異構物相對穩定的構形,進行13C NMR化學位移計算,並與已報導之數值做比對。我們採用GIAO/HF、GIAO/DFT/OPBE及GIAO/DFT/B3LYP搭配四種不同的基底函數,包括6-311++G(d,p)、6-311+G(2d,p)、cc-pVDZ及cc-pVTZ做單點計算。相對穩定的構形,其13C NMR化學位移之平均絕對誤差(Mean Absolute Error,MAE)也相對較小。因為實驗的化學位移是許多構形的平均貢獻,我們考慮Boltzmann分佈將數個構形混合去進行13C NMR化學位移計算,構形混合的MAE比單一構形的MAE小,而且實驗的化學位移和理論計算的化學位移趨勢符合。其中使用HF(Hartree-Fock,HF)方法搭配cc-pVTZ基底函數,使用OPBE方法搭配6-311+G(2d,p)基底函數及使用B3LYP方法搭配cc-pVDZ基底函數,計算所得之化學位移最接近實驗值。針對其他相關結構易變的七圓環醣水解酵素抑制劑,此結果可以作為參考的依據。 |
英文摘要 |
Owing to the conformational flexibility for trihydroxyazepanes, the theoretical prediction should be helpful for generating appropriate conformations. DFT/B3LYP/6-311++G(d,p) calculations of three isomers for trihydroxyazepanes are presented to obtain 28 conformations for each isomer. The Boltzmann distribution was considered to calculate the population of each conformation. The GIAO/DFT/OPBE, GIAO/DFT/B3LYP and GIAO/HF single point calculations with four different basis sets, including 6-311++G(d,p), 6-311+G(2d,p), cc-pVDZ and cc-pVTZ of the relative stable conformations of trihydroxyazepanes were conducted to generate their 13C NMR chemical shifts. The calculated chemical shifts are compared with the experimental ones. The MAEs (Mean Absolute Error, MAE) of the 13C NMR chemical shifts for the relative stable conformations are smaller. Moreover, the experimental 13C NMR chemical shifts gave only the average contribution of all conformations. The observed average chemical shifts displays improvement over that of each individual conformation. Good choices to evaluate the theoretical chemical shifts for these conformations are HF/cc-pVTZ, OPBE/6-311+G(2d,p) and B3LYP/cc-pVDZ. The calculated 13C NMR chemical shifts are in good agreement with the experimental NMR data of trihydroxyazepanes. |
第三語言摘要 | |
論文目次 |
中文摘要 I 英文摘要 II 目錄 III 表目錄 VI 圖目錄 X 第一章 緒論 1 1-1 前言 1 1-2 醣水解酵素 5 1-3 醣水解酵素抑制劑 6 1-3-1可逆性抑制劑 6 1-3-2不可逆性抑制劑 7 1-4醣水解酵素抑制劑的結構 9 1-5核磁共振 12 1-6研究概況 14 1-7 研究動機 23 第二章 量子化學計算理論與方法 25 2-1 前言 25 2-2 量子力學 28 2-2-1 薛丁格方程式(Schrödinger Equation) 29 2-2-2 原子單位(Atomic Units) 32 2-2-3 波恩-歐本海莫(Born-Oppenheimer)近似法 33 2-2-4 分子軌域理論 35 2-3量子化學計算近似法 37 2-3-1 Hartree — Fock量子化學計算近似法 37 2-3-2密度泛函數理論 42 2-4基底函數組(Basis Set) 49 2-4-1最小基底函數STO-3G 52 2-4-2分離價層的基底函數(Split-Valence Basis Sets) 54 2-4-3極化函數(Polarization Function) 55 2-4-4擴散函數(Diffuse Function) 57 2-4-5考慮相干的基底函數(Correlation Consistent basis set) 58 2-5分子性質(Molecular Properties) 59 2-5-1外加磁場的微擾處理( Molecular Field Perturbation ) 60 2-5-2分子磁性的原點關連性( Gauge Dependence ) 62 2-6 13C化學位移 64 第三章 研究設備 65 3-1 硬體設備 65 3-2 軟體設備 65 第四章 Trihydroxyazepanes的結構與化學位移 69 4-1 簡介 69 4-2 研究方法 70 4-3結果與討論 72 4-3-1 (3R,4R,5R)-trihydroxyazepanes 72 4-3-1-1分子幾何結構 72 4-3-1-2 13C NMR化學位移 90 4-3-2 (3R,4R,6S)-trihydroxyazepanes 106 4-3-2-1分子幾何結構 106 4-3-2-2 13C NMR化學位移 118 4-3-3 (3S,4R,6S)-trihydroxyazepanes 137 4-3-3-1分子幾何結構 137 4-3-3-2 13C NMR化學位移 149 第五章 結論 185 A.參考文獻 187 B.相關著作 195 |
參考文獻 |
A. 參考文獻 [1] 何銳,為什麼要學化學,海鴿文化,2007。 [2] 呂鋒洲,酵素精義學,藝軒出版社,1992。 [3] 呂鋒洲,林仁混,基礎酵素學,聯經出版社,1991。 [4] 陳貞吟,醣水解酵素活性標示設計及合成之研究(碩士論文),台灣大學化學研究所,2001。 [5] Itzstein, M. V.; Dyason, J. C.; Oliver, S. W.; White, H. F.; Wu, W. -Y.; Kok, G. B.; Pegg, M. S. J. Med. Chem. 1996, 39, 388. [6] Wilson, J. C.; Thomson, R. J.; Dyason, J. C.; Florio, P.; Quelch, K. J.; Abo, S.; Itzstein, M. V. Tetrahedron:Asymmetry 2000, 11, 53. [7] Nishimura, Y.; Shitara, E.; Adachi, H.; Toyoshima, M.; Nakajima, M.; Okami, Y.; Takeuchi, T. J. Org. Chem. 2000, 65, 2. [8] Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681. [9] Walsh, C. Tetrahedron 1982, 38, 871. [10] Rando, R. R.; Science 1974, 185, 320. [11] 蔡長昇,醣水解酵素活性標示之開發及其在蛋白質體學上的應用(碩士論文),台灣大學化學研究所,2002。 [12] Painter, G. F.; Eldridge, P. J.; Falshaw, A. Bioorg. Med. Chem. 2004, 12, 225. [13] Lin, C. -C.; Pan, Y. -S.; Patkar, L. N.; Lin, H. -M.; Tzou, D. -L. M.; Subramanian, T.; Lin, C. -C. Bioorg. Med. Chem. 2004, 12, 3259. [14] 楊如盈,利用D-(-)-quinic acid合成3,4,6-trihydroxyazepanes及含有N-beneyl之衍生物作為具有潛力之醣水解酵素抑制劑(碩士論文),淡江大學化學研究所,2005。 [15] 司寇克,儀器分析,美亞書版股份有限公司,1994。 [16] Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497. [17] Magyarfalvi, G.; Pulay, P. J. Chem. Phys. 2003, 119, 1350. [18] Wilson, P. J.; Amos, R. D.; Handy, N. C. Chem. Phys. Lett. 1999, 312, 475. [19] Zhang, Y.; Wu, A.; Xu, X.; Yan, Y. Chem. Phys. Lett. 2006, 421, 383. [20] Paulsen, H.; Todt, K. Chem. BER.1967, 100, 512. [21] Tilekar, J.N.; Patil, N.T.; Jadhav.H.S.; Dhavale. D. D. Tetrahedron 2003, 59, 1873. [22] Li, H. ; Bleriot,.Y.; Mallet, J. M. ;Rodriguez-Garcia, E.; Vogel,. P.; Zhang, Y. ;Sinay, P. Tetrahedron: Asymmetry 2005, 16, 313. [23] Shih, T. L.; Yang, R. Y.; Chiang, C. F.; Li, C. H. J. Org. Chem. 2007, 72, 4258. [24] Karina, M.-M.; José L, M.-F.; Silvia, M.; Cañada, F. J.; Eliazar, R.-G.; Pierre, V.; Li, H.; Yves, B.; Pierre, S.; Jesús, J.-B. Eur. J. Org. Chem. 2004, 4119. [25] Lobato-Garcia,C. E.; Gauadarrama, P.; Lozada,C.; Enriquez,D. G.; Reynolds, W. F. J. Mol. Struc. 2006, 786, 53. [26] deOliveira, K. T.; Junior, V. L.; Constantino, M. G.; Donate, P. M.; dasilva, G. V. J.; Brocksom, T. J.; Fredevico, D. Spectrochim. Acta Part A 2006, 63 , 709. [27] DeMatteo, M. P.; Snyder, N. L.; Morton, M.; Baldisseri, D. M.; Hadad, C. M.; Peczuh, M. W. J. Org. Chem. 2005, 70 , 24. [28] Tilekar, J. N.; Patil, N. T.; Jadhav, H. S.; Dhavale, D. D. Tetrahedron 2003, 59, 1873. [29] Dhavale, D. D.; Chaudhari, V. D.; Tilekar, J. N. Tetrahedron Lett. 2003, 44, 7321. [30] 許世宜;許文賢; Peter, J. R. 化學,1994, 52, 170. [31] 王鴻偉,奈米管與球烯衍生物的結構與電子性質之理論計算研究(博士論文),淡江大學化學研究所,2003。 [32] 左希軍,球烯多元醇與不對稱氫化反應之理論探討(博士論文),淡江大學化學研究所,2002。 [33] Alsenoy, C. V.; Peeters, A. J. Mol. Struct. (THEOCHEM) 1993, 105, 19. [34] Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187. [35] Alsenoy, C. V. J. Comput. Chem. 1988, 9, 620. [36] Levine, I. N. Quantum Chemistry, 4th ed.; Prentice Hall: New York, 1991. [37] 劉東昇,化學量子力學,徐氏基金會: 台北縣, 1998。 [38] Szabo, A.; Ostlund, N. S. Modern Quantum Chemistry, 1st ed.; McGRAW-HILL: New York, 1982. [39] Frisch, Æ.; Foresman, J. B. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996. [40] HyperChem®, Computational Chemistry, Hypercube, inc.: Waterloo, Ontario, 1996. [41] Hehre, W. J.; Yu, J.; Klunzinger, P. E.; Lou, L. A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations, Wavefunction, Inc.: Irvine, CA, 1998. [42] Ransil, B. J. Rev. Mod. Phys. 1960, 32, 245. [43] Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864. [44] Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133. [45] 張金泉,有機光電材料之理論計算研究(博士論文),淡江大學化學研究所,2002。 [46] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery J. J. A.; Vreven, T., Kudin, K. N.; Burtant J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui,Q.; Baboul, A. G.; Clifford, S. Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalea, C.; Pople, J. A. Gaussian 03, Revision 6.0 C.02, Gaussian Inc., Pittsburgh, PA, 2004. [47] Cohen, A. J.; Handy, N. C. Phys. Lett. 2000, 316, 160. [48] Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865. [49] Jensen, F. Introduction to Computational Chemistry, John Wiley & Sons: New York, 1999. [50] Schindler, M.; Kutzelnigg, W. J. Chem. Phys. 1982, 76, 1919. [51] Hansen, A. E.; Bouman, T. D. J. Chem. Phys. 1985, 82, 5035. [52] London, F. J. Phys. Radium. 1937, 8, 397. [53] Ditchfield, R. Mol. Phys. 1974, 27, 789. [54] Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223. [55] HyperChem®, Whats New in Release 6, Hypercube, inc.: Waterloo, Ontario, 1999. [56] Frisch, Æ.; Frisch, M. J. Gaussian 98 User’s Reference, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1999. [57] Groopman, J. E. Rev. Infect. Dis. 1990, 12, 908. [58] Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605. [59] Papandreou, M.-J.; Barbouche, R.; Guieu, R.; Kieny, M. P.; Fenouillet, E. Mol. Pharmacol. 2002, 61, 186. [60] White, S. L.; Nagai, T.; Akiyama, S. K.; Reeves, E. J.; Grzegorzewski, K.; Olden, K. Cancer Commun. 1991, 3, 83. [61] Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. [62] Rye, P. D.; Bovin, N. V.; Vaslova, E.; Walker, R. A. Glycobiology, 1995, 5, 385. [63] Elbein, A. D.; Molyneux, R. D. in Imino Sugars as Glycosidase Inhibitors: Nojirimycin and Beyond (Ed.: Stutz), Wiley-VCH, Weinheim, 1999, chapter 11, pp. 216. [64] Zitzmann, N.; Mehta, A. S.; Carrouee, S.; Butters, T. D.; Platt, F. M.; McCauley, J.; Blumberg, B. S.; Dwek, R. A.; Block, T. M. PNAS, 1999, 96,11878. [65] Asano, N. J. Enzyme Inhibition, 2000, 15, 215. [66] Mitrakou, A.; Tountas, N.; Raptis, A. E.; Bauer, R. J.;Schulz, H.; Raptis, S. A. Diab. Med. 1998, 15, 657. [67] O’Hagan, D. Nat. Prod. Rep. 2000, 17, 435. [68] Wu, X.; Toppet, S.; Compernolle, F.; Hoornaert, G. J. Tetrahedron 2000, 56, 6279. [69] Hu, X. E.; Kim, N.K.; Gray, J. L.; Almstead, J. K. ; Seibel, W. L.; Ledoussal, B. J. Med. Chem. 2003, 46, 3655. [70] Thamotharan, S.; Parthasarathi, V.; Gupta, P.; Jindal, D. P.; Piplani, P.; Linden, A. Acta Crystallogr. 2003, E59, o1334. [71] Kenda, B. M.; Matagne, A. C.; Talaga, P. E.; Pasau, P. M.; Differding, E.; Lallemand, B. I.; Frycia, A. M.; Moureau, F. G.; Klitgaard, H. V.; Gillard, M. R.; Fuks, B.; Michel, P. J. Med. Chem. 2004, 47, 530. [72] Tamazyan, R.; Karapetyan, H.; Martirisyan, A.; Martirosyan, V.; Harutyunyan, G.; Gasparyan,S. Acta Crystallogr. 2004, C60, o390. [73] Poitout, L.; Le Merrer, Y.; Depazy, J.-C. Tetrahedron Lett. 1994, 35, 3293. [74] Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60 , 5958. [75] Poitout, L.; Le Merrer, Y.; Depazy, J.-C. Tetrahedron Lett. 1996, 37, 1613. [76] Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron Lett. 1999, 40, 4063. [77] Herdeis, C.; Mohareb, R. M.; Neder, R. B.; Schwabenlander, F.; Tesler, J. Tetrahedron:Asymmetry 1999, 10, 4521. [78] Lohray, B. B.; Bhushan, V.; Prasuna, G.; Jayamma, Y.; Raheem, M. A.; Papireddiy, P.; Umadevi, B.; Premkumar, M.; Lakshmi, N. S.; Narayanreddy, K. Indian J. Chem. 1999, 38B, 1311. [79] Painter, G. F.; Falshaw, A. J. Chem. Soc., Perkin Trans. 1 2000, 1157. [80] Armbruster, J.; Stelzer, F.; Landenberger, P.; Wieber, C,; Hunkler, D.; Keller, M.; Prinzbach, H. Tetrahedron Lett. 2000, 41, 5483. [81] Li, H.; Bleriot, Y.; Chantereau, C.; Mallet, J. M.; Sollogoub, M.; Zhang, Y.; Rodriguez-Garcia, E.; Vogel, P.; Jimenez-Barbero, J.; Sinay, P. Org. Biomol. Chem. 2004, 2, 1492. [82] Li, H.; Schutz, C.; Favre, S.; Zhang, Y.; Vogel, P.; Sinay, P.; Bleriot, Y. Org. Biomol. Chem. 2006, 4, 1653. [83] Belostotskii, A. M.; Gottlieb, H. E.; Aped, P.; Hassner, A. Chem.Eur. J. 1999, 5, 449. [84] Delpuech, J. J.; in: Lambert, J. B.; Takeuchi, Y. (Eds.), Cycli Organonitrogen Stereodynamics, VCH Publishers, New York, 1992, (Chapter 7). [85] Riddel, F. G.; in: Lambert, J. B.; Takeuchi, Y. (Eds.), Cycli Organonitrogen Stereodynamics, VCH Publishers, New York, 1992, (Chapter 6). [86] Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021. [87] Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199. [88] Wong, C. H.; Halcomb, R. L.; Ichikawa, Y.; Kajimato, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521. [89] Moris-Varas, F.; Qian, X.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 7647. [90] Qian, X.; Moris-Varas, F.; Fitzgerald, M. C.; Wong, C. H. Bioorg. Med. Chem. 1996, 4, 2055. [91] Le Merrer, Y.; Poitout, L.; Depazy, J.-C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M. Bioorg. Med. Chem. 1997, 5, 519. [92] Marchand, A. P. Stereochemical Applications of NMR Studies in Rigid System, Verlag Chemie International, Deerfield Beach, FL, 1982. [93] Marchand, A. P. in: R. P. Thummel (Ed.), Advances in Theoretically Interesting Molecules,Greenwich, CT, vol. 1, 1989, p.357. [94] Encyclopedia of NMR, edited by Grant D. M. and Harris R. K. (Wiley& Sons, England, 1996). [95] Perera, S. A.; Bartlett, R. J.; Schleyer, P. J. Am. Chem. Soc. 1995, 117, 8476. [96] Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 203. [97] Rossi, P.; Harbison, G. S. J. Magn. Reson. 2001, 151, 1. [98] Constantino, M. G.; da Silva Filho, L. C.; Neto, A. C.; Heleno, V. C. G.; da Silva, G. V. J.; Lopes, J. L. C. Spectrochim. Acta Part A 2004, 6, 171. [99] Galasso, V. J. Mol. Struct. (THEOCHEM) 2000, 528, 171. [100] Wiberg, K. B. J. Org. Chem. 2003, 68, 9322. [101] Tormena, C. F.; da Silva, G. V. J. D. Chem. Phys. Lett. 2004, 398, 466. [102] Qian, X.; Moris-Varas, F.; Fitzgerald, M. C.; Wong, C. H. Bioorg.&Med. Chem. 1996, 4, 2055. [103] Alkorta, I.; Elguero, J. J. Magn. Reson. 2004, 42, 955. [104] Migda, W.; Rys, B. J. Org. Chem. 2006, 71, 5498. [105] Ilczyszyn, M.; Godzisz, D.; Ilczyszyn, M. M.; Mierzwicki, K. Chem. Phys. 2006, 323, 231. [106] 賴文偉,利用高壓紅外線光譜研究1,3-dioxane水溶液中的類氫鍵(hydrogen bond-like) equatorial C–H…O作用力(碩士論文),東華大學化學系,2005。 [107] Barone, G.; Duca, D.; Silvestri, A.; Gomez-Paloma, L.; Riccio, R.; Bifulco, G. Chem. Eur. J. 2002, 8, 3240. B. 相關著作 [1] Tai, C. K.; Lin, Y. J.; Yeh, P. L.; Tzeng, Y. R.; Chou, Y. M.; Wang, B. C. J. Mol. Struct. (THEOCHEM) 2008, 860, 58. Effects of substituent and solvent on the structure and spectral properties of maleimide derivatives [2] Tai, C. K.; Chen, Y. J.; Chang, H. W.; Yeh, P. L.; Wang, B. C. J. Mol. Struct. (THEOCHEM) 2011 (accepted) DFT and TD-DFT Investigations of Metal-Free Dye Sensitizers for Solar Cells: Effects of Electron Donors and π-Conjugated Linker [3] Yeh, P. L.; Tai, C. K.; Shih, T. L.; Hsiao, H. L.; Wang, B. C. J. Mol. Struct. 2011 (revision) Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts |
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