对称四甲基取代六元瓜环与客体相互作用的NMR研究
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摘要
本论文用NMR研究了对称四甲基六元瓜环与一系列客体分子的相互作用，共分两部分内容。
第一部分是利用2D NMR研究对称四甲基六元瓜环与吡啶芳香衍生物的相互作用。运用~1H-~1H ROESY等各种核磁共振二维实验，对TMeQ[6]与吡啶芳香衍生物如2-氨甲基吡啶，5，5′-二甲基-2，2′-联吡啶以及2，2′-联吡啶(简称ampy，bmbpy和bpy)的相互作用进行了研究。2D ROESY谱上清晰地呈现了主、客体分子间的NOE相关峰，直接给出了二者结合时的相对位置等结构信息。ampy-TMeQ[6]X-ray晶体衍射结构与NOE所得结果一致。
二维交换谱(2D EXSY)的研究表明，在TMeQ[6]与bmbpy 1：1结合物中，温度升高时客体bmbpy上的两个吡啶环不断地交替穿梭进入TMeQ[6]的腔体内部，形成了结合位置上的交换，使得TMeQ[6]与bmbpy的结合处于一种动态的平衡，通过对2D EXSY上相关峰和对角线峰强度的计算得到了这种交换的速度常数和活化能等热力学常数。对2，2′-联吡啶与TMeQ[6]相互作用的研究结果也表明同样存在着这种交换的动态平衡。与bmbpy相比，它与TMeQ[6]结合位置动态交换的活化能需要减少22.0 kj／mol，在相同的温度下交换速率加快。
第二部分设计了一个以TMeQ[6]为主体的分子开关。利用定量氢谱的方法，求得TMeQ[6]与一系列客体的结合常数，并根据客体的结合常数以及他们的pKa值，我们找到两个客体分子bpy(强结合客体)和正庚胺(弱结合客体)，他们与TMeQ[6]组成一个三元体系，通过调节pH值成功的实现了第一个同一葫芦脲主体在不同客体分子间形成的分子开关。
In this thesis, evidence for inclusion complexation in solution between the synthetic receptor symmetrical tetramethylcucurbit[6]uril (TMeQ[6]) , and a series of alkyl-and aryl-substituted ammonium ion ligands is elaborated by NMR. The thesis consists of two parts.
In part one, complexation between symmetrical tetramethylcucurbit[6]uril (TMeQ[6]) and 2-(Aminomethyl) pyridine (ampy), 5, 5'-bimethy-2, 2'-bipyridine (bmbpy) and 2, 2'-bipyridine (bpy) was studied by two dimensional nuclear magnetic resonance (2D NMR) as a host-guest interaction. Intermolecular NOEs appeared in 2D ROESY spectrum reveal a well-defined complex structure between them.
~1H exchange spectroscopy (2D EXSY) showed that the 1:1 complex between TMeQ[6] and bmbpy is undergoing slow exchange at high temperature with two pyridine rings of bmbpy alternatively entering the cavity of TMeQ[6] and changing the combinative sites between the two portals of TMeQ[6]. The temperature dependence of the rate constants calculated from the EXSY spectra yielded an activation energy of 104. 2 kJ /mol for the exchange process.
In part two, a TMeQ[6]-based intramolecular switch is designed. Dissociation constants (Kd) for a series of alkyl-and aryl-substituted ammonium ion ligands is measured by quantitative ~1H NMR integration. While the stabilities of TMeQ[6] and many ammonium ion ligands complexes strongly depend on pH, and the Kd values have a large difference, bpy, C7H15NH3+ and TMeQ[6] is choiced to compose a three compounds system in which TMeQ[6] exhibits a bimodal binding pattern contingent upon pH.
第一部分是利用2D NMR研究对称四甲基六元瓜环与吡啶芳香衍生物的相互作用。运用~1H-~1H ROESY等各种核磁共振二维实验，对TMeQ[6]与吡啶芳香衍生物如2-氨甲基吡啶，5，5′-二甲基-2，2′-联吡啶以及2，2′-联吡啶(简称ampy，bmbpy和bpy)的相互作用进行了研究。2D ROESY谱上清晰地呈现了主、客体分子间的NOE相关峰，直接给出了二者结合时的相对位置等结构信息。ampy-TMeQ[6]X-ray晶体衍射结构与NOE所得结果一致。
二维交换谱(2D EXSY)的研究表明，在TMeQ[6]与bmbpy 1：1结合物中，温度升高时客体bmbpy上的两个吡啶环不断地交替穿梭进入TMeQ[6]的腔体内部，形成了结合位置上的交换，使得TMeQ[6]与bmbpy的结合处于一种动态的平衡，通过对2D EXSY上相关峰和对角线峰强度的计算得到了这种交换的速度常数和活化能等热力学常数。对2，2′-联吡啶与TMeQ[6]相互作用的研究结果也表明同样存在着这种交换的动态平衡。与bmbpy相比，它与TMeQ[6]结合位置动态交换的活化能需要减少22.0 kj／mol，在相同的温度下交换速率加快。
第二部分设计了一个以TMeQ[6]为主体的分子开关。利用定量氢谱的方法，求得TMeQ[6]与一系列客体的结合常数，并根据客体的结合常数以及他们的pKa值，我们找到两个客体分子bpy(强结合客体)和正庚胺(弱结合客体)，他们与TMeQ[6]组成一个三元体系，通过调节pH值成功的实现了第一个同一葫芦脲主体在不同客体分子间形成的分子开关。
In this thesis, evidence for inclusion complexation in solution between the synthetic receptor symmetrical tetramethylcucurbit[6]uril (TMeQ[6]) , and a series of alkyl-and aryl-substituted ammonium ion ligands is elaborated by NMR. The thesis consists of two parts.
In part one, complexation between symmetrical tetramethylcucurbit[6]uril (TMeQ[6]) and 2-(Aminomethyl) pyridine (ampy), 5, 5'-bimethy-2, 2'-bipyridine (bmbpy) and 2, 2'-bipyridine (bpy) was studied by two dimensional nuclear magnetic resonance (2D NMR) as a host-guest interaction. Intermolecular NOEs appeared in 2D ROESY spectrum reveal a well-defined complex structure between them.
~1H exchange spectroscopy (2D EXSY) showed that the 1:1 complex between TMeQ[6] and bmbpy is undergoing slow exchange at high temperature with two pyridine rings of bmbpy alternatively entering the cavity of TMeQ[6] and changing the combinative sites between the two portals of TMeQ[6]. The temperature dependence of the rate constants calculated from the EXSY spectra yielded an activation energy of 104. 2 kJ /mol for the exchange process.
In part two, a TMeQ[6]-based intramolecular switch is designed. Dissociation constants (Kd) for a series of alkyl-and aryl-substituted ammonium ion ligands is measured by quantitative ~1H NMR integration. While the stabilities of TMeQ[6] and many ammonium ion ligands complexes strongly depend on pH, and the Kd values have a large difference, bpy, C7H15NH3+ and TMeQ[6] is choiced to compose a three compounds system in which TMeQ[6] exhibits a bimodal binding pattern contingent upon pH.
引文
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30．丛航，《瓜环的主客体化学研究》，华东师范大学硕士毕业论文，2005
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15. Isobe, H.; Sato, S.; Nakamura, E. Organ. Letters, 2002, 4, 1287.
16. Dantz, D.; Meschke, C.; Buschmann, H.-J.; Schollmeyer, E. Supramol. Chem. 1998, 9, 79.
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19. Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440.
20. Luo, X.-Q.; Zhang, G.-L.; Xue, S.-F.; Tao, Z.; Zhu, Q.-J. J. Guizhou Univ.(Nat. Sci. Ed)2003, 20, 3(in Chinese)．(罗绪强，张桂玲，薛赛风，陶朱，祝黔江，贵州大学学报，(自然科学版)，2003，20，3．)21. Zhao, Y.-J; Xue, S.-F; Zhu, Q.-J; Tao, Z.; Zhang, J.-X.; Wei, Z.-B.; Long, L.-S.; Hu, M.-L.; Xiao, H.-P.; Day, A. I. Chin. Sci. Bull. 2004, 49, 1111(in Chinese).(赵云洁，薛赛凤，祝黔江，陶朱，张建新，魏赞斌，龙腊生，胡茂林，肖洪平，Day Anthony I，科学通报，2004，49，1111．)
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23. Zhao, Y.-J.; Xue, S.-F.; Zhang, Y.-Q.; Zhu, Q.-J.; Tao, Z.; Zhang, J.-X.; Wei, Z.-B.; Long, L.-S. Acta Chimica Sinica, 2005, 63, 913(赵去洁，薛赛凤，张云黔，祝黔江，陶朱，张建新，魏赞斌，龙腊生，化学学报，2005，63，913)
24. Isobe, H.; Sato, S.; Nakamura, E. Organ. Letters, 2002, 4, 1287
25. Oh, K.-S.; Yoon, J.; Kim, K.-S. J. pHys. Chem. B, 2001, 105, 9726
26. Day, A.-I.; Arnold, A.-P.; Blanch, R.-J. Molecules, 2003, 8, 74
27. Jansen, K.; Wego, A.; Buschmann, H.-J.; et. al. Designed Monomers and Polymers, 2003, 6, 43
28. Bumett, C.-A.; Witt, D.; Fettinger, J.-C.; Isaacs, L. J. Org. Chem. 2003, 68, 6184
29. Jon, S.-Y.; Selvapalam, N.; Oh, D.-H.; Kang, J.-K.; Kim, S.-Y.; Jeon, Y.-J.; Lee, J.-W.; Kim, K. J. Am. Chem. Soc., 2003, 125, 10186
30．丛航，《瓜环的主客体化学研究》，华东师范大学硕士毕业论文，2005
31. Han, B.-H.; Liu, Y. Chinese Journal of Organic Chemistry 2003, 23, 139(in Chinese)．(韩宝航，刘育，有机化学 2003，23，139)
32. Buschmann, H.-J.; Cleve, E.; Schollmeyer, E. lnorg. Chem. Acta 1992, 103, 93.
33. Buschmann, H.-J.; Jansen, K.; Meschke, C.; Schollmeyer, E. J. Solution Chem. 1998, 27, 135.
34. Buschmann, H.-J.; Cleve, E.; Jansen, K.; Wego, A.; Scholleyer, E. J. Incusion pHenom. Mol. Recognit. Chem. 2001, 40, 117.
35. Buschmann, H.-J.; Cleve, E.; Jansen, K.; Scholleyer, E. Anal. Chim. Acta 2001, 437, 157.
36. Zhang, X.-X.; Krakowiak, K.-E.; Xue, G.; Bradshaw, J.-S.; Izatt, R.-M. Ind Eng. Chem. Res. 2000, 39, 3516.37. Lorenzo, S.; Day, A.; Craig, D.; Blanck, R.; Arnold, A.; Dance, I. Cryst. Eng. Comm., (online computer file) 2001, 49, 1.
38. Lorenzo, S.; Day, A.; Craig, D.; Blanck, R.; Arnold, A.; Dance, I. Cryst. Eng. Comm., 2001, 491
39. Mock, W.-L.; Shih, N.-Y. J. Org. Chem. 1983, 48, 3617.
40. Mock, W.-L.; Shih, N.-Y. J. Am. Chem. Soc. 1988, 110, 4706.
41. Buschmann, H.-J.; Schollmeyer, E. J. Incusion pHenom. Mol. Recognit. Chem. 1992, 14, 91.
42. Wagner, B.-D.; MacRae, A.-I. J. pHys. Chem. B 1999, 103, 10114.
43. Kim, H.-J.; Heo, J.; Jeon, W.-S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526.
44. Buschmann, H.-J.; Jansen, K.; Schollmeyer, E. Thermochim. Acta 1998, 317, 95.
45. Buschmann, H.-J.; Jansen, K.; Schollmeyer, E. Thermochim. Acta 2000, 346, 33.
46. Jansen, K.; Buschmann, H.-J.; Wego, A.; DEpp, D.; Mayer, C.; Drexler, H.-J.; Holdt, H.-J.; chollmeyer, E. J. Incusion pHenom. Mol. Recognit. Chem. 2001, 39, 357.
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