几类化合物中的分子间弱相互作用研究
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摘要
由于在晶体工程学、分子识别、超分子化学、超分子组装、晶体堆积和生物体系的构效关系等研究领域中所起的重要作用,分子间弱相互作用的研究越来越引起研究者们的重视,并逐渐形成一个热门的领域。近年来,从实验和量子化学的角度对一些分子间弱相互作用的研究已有大量报道,但是,关于分子间弱相互作用体系的量子拓扑研究还比较少见。
本文的研究目的在于利用量子化学和量子拓扑学的电子密度方法研究一些弱相互作用体系的结构和性质,从而对这些弱相互作用形成的特性做出描述和分析,为弱相互作用的深入研究提供理论基础。本文主要针对经典的共振氢键、非经典的C—H…O氢键、C—H…π作用、π…π堆积这四种类型的弱相互作用进行详细的研究和讨论。
本文的第一章对弱相互作用的研究现状,量子化学基本原理与量子拓扑学理论的发展历史进行了简单的回顾和介绍。量子化学的应用研究范围正在不断扩大,化学键和分子的电子结构仍然是量子化学研究的主要内容,而量子拓扑学作为一个新兴的理论还需要不断发展。
本文的第二章利用晶体化学、量子化学和量子拓扑学方法对邻羟基偶氮苯化合物中的N—H…O/O—H…N共振氢键进行了详细的研究。从几何构型、氢键强度和氢键性质等方面进行相关讨论。证明在邻羟基偶氮苯化合物中N—H…O/O—H…N共振氢键普遍存在,O—H…N氢键强于N—H…O氢键,且N—H…O/O—H…N共振氢键的本质为三中心四电子的共价键模式。并对两个偶氮化合物a201和a202的单品结构进行了详细分析:这两个偶氮化合物分子在堆积成三维晶体时,主要依靠的是一些分子间弱相互作用,包括:C—H…O、C—H…N、C—H…Cl等弱氢键以及π…π堆积作用和C—H…π作用,并对类似的卤素取代偶氮苯分子进行了CSD检索分析。发现π…π堆积和C—H…π作用在这些分子中普遍存在着,它们的强度不大但却主导着分子的自组装过程。π…π堆积和C—H…π作用大多与对称中心相联系,属于中心对称的弱相互作用。此外,这类体系中还有大量的常规氢键存在,如C—H…O、C—H…N、C—H…X(Cl、Br)等,虽然是弱氢键但在分子自组装过程中也起重要作用。这些氢键大部分是与平移、螺旋轴和滑移面相联系的,属于非中心对称的氢键。这些数据与结论可以为非线性光学材料的设计提供重要的参考。
本文的第三章对4,4'-查尔酮化合物中的多中心C—H...O氢键进行了详细研究。从晶体结构的几何参数、量子化学的结构优化和能量计算以及量子拓扑学的电子密度分析三方面证明了此类化合物中R_3~1(11)型的C—H...O氢键的确存在。同时对β-羟基查尔酮和2'-羟基查尔酮化合物中的O—H...O共振氢键也进行了晶体化学、量子化学和量子拓扑学的详细研究。从几何构型、氢键强度和氢键性质等几个方面进行了讨论。证明在此类化合物中O—H...O共振氢键普遍存在,且O—H...O共振氢键的本质是三中心四电子的共价键模式。此外对氢键的距离、氢键临界点处的电子密度以及氢键能三者之间的线性相关性进行了量子拓扑学研究,结果表明这三者间存在比较好的线性相关性,同时也说明了键临界点处的电子密度等拓扑性质可以较好地表征氢键的强度和性质,AIM方法可以作为表征氢键等弱相互作用的直观有效的工具。
本文的第四章通过剑桥晶体结构数据库检索比较了27个苯乙烯吡啶盐中的C—H…π作用。这27个物质根据阴阳离子的种类分成四类,分别就其中的C—H…π、π…π作用的特点以及晶体堆积能、离子间相互作用能与中心对称晶体形成之间的相互关系进行了讨论。结果表明,阳离子相同时,若阴离子体积较大,由于有比较大的库仑力,有利于克服阳离子间的偶极相互作用,此时分子堆积为晶体时的空间群形式很大程度上取决于C—H…π、π…π等弱相互作用的连接方式。若这些弱相互作用以对称中心相联系,则堆积为中心对称的晶体;若阴离子体积较小,由于不能有效屏蔽阳离子的偶极效应,因此极易以中心对称的空间群堆积,但是若能引入分子内强氢键则有可能改变堆积方式。这些结论可以为非线性光学材料的设计提供参考。
Because of the vital role in the crystal engineering,the molecular recognition, supramolecular chemistry,the supramolecular assembly,crystal packing and the structure-activity relationship in biological systems,the study on the molecular weak interactions has attracted the attention of researchers.In recent years,the molecular weak interactions are being paid more attention to the experimental and theoretical investigations.But it is seldom about the weak interactions by topological analysis methods.
The purpose of this paper is to study the geometry configuration,bonding nature by quantum chemistry and topological analysis of the electronic density methods.The rules of the formation of molecular weak interactions were discussed in order to help the further research in this field.In this thesis,the four types of weak interactions such as conventional resonance-assisted hydrogen bond,non-conventional C—H…O hydrogen bond,C—H…πinteraction andπ…πstacking were studied.
At the first part of the thesis,the wide application of weak interaction,quantum chemistry and topological analysis was summarized.Bonding characters and electronic structures are still the main area of quantum chemical research.Because the topological analysis of the electronic density method is a new method,many studies are needed to be done by the theory.
In chapter two,the resonance-assisted N—H…O/O—H…N hydrogen bond in hydroxyl azobenzene were studied by crystal chemistry,quantum chemistry and topological analysis.The results lead us to the conclusion that the N—H…O hydrogen bond is stronger than O—H…N hydrogen bond in hydroxyl azobenzene,and this resonance-assisted hydrogen bond is best described as a 3-center,4-electron covalence bond.The structures of two azobenzene single crystals were also studied.The results show that the weak molecular interactions such as C—H…O、C—H…N、C—H…Cl hydrogen bond,π…πstacking and C—H…πinteraction play important role in crystal packing.The results of CSD(Cambridge Structural Database) searches also show thatπ…πstacking and C—H…πinteraction dominate the molecular assembly.π…πstacking and C—H…πinteractions are usually contacted by centrosymmetry,and C—H…O、C—H…N hydrogen bonds are noncentrosymmetric hydrogen bond.
In chapter three,the multi-center C—H...O hydrogen bond was studied.The geometry configuration,quantum calculation and electronic density analysis made us sure that R_3~1(11) multi-center C—H...O hydrogen bond was existed for a certainty in 4,4'-chalcone compounds.It was also testified that the characteristic of O—H...O resonance-assisted hydrogen bond was a 3-center,4-electron covalence bond.Linear correlations of the interaction energies with the electronic density in the hydrogen bond and the lengths of hydrogen bond were discussed.
In chapter four,the crystal structures of 27 stilbazolium salts were retrieved from CSD.The relationship among the characteristic ofπ…πstacking and C—H…πinteraction,crystal packing energies and formation of centrosymmetric crystal was discussed.The results indicated that when the stilbazolium salts have got the same cations,the large anions can provide strong electrostatic interactions to overcome the dipole-dipole interactions.In this condition,the connected methods of C—H…πandπ…πweak interactions will master the type of space group of crystal packing.If these weak interactions were connected by centrosymmetry,the compounds are accumulated in centrosymmetric space groups.The compounds will accumulated in centrosymmetric space groups if the volume of anions is not large enough to overcome dipole interactions.
本文的研究目的在于利用量子化学和量子拓扑学的电子密度方法研究一些弱相互作用体系的结构和性质,从而对这些弱相互作用形成的特性做出描述和分析,为弱相互作用的深入研究提供理论基础。本文主要针对经典的共振氢键、非经典的C—H…O氢键、C—H…π作用、π…π堆积这四种类型的弱相互作用进行详细的研究和讨论。
本文的第一章对弱相互作用的研究现状,量子化学基本原理与量子拓扑学理论的发展历史进行了简单的回顾和介绍。量子化学的应用研究范围正在不断扩大,化学键和分子的电子结构仍然是量子化学研究的主要内容,而量子拓扑学作为一个新兴的理论还需要不断发展。
本文的第二章利用晶体化学、量子化学和量子拓扑学方法对邻羟基偶氮苯化合物中的N—H…O/O—H…N共振氢键进行了详细的研究。从几何构型、氢键强度和氢键性质等方面进行相关讨论。证明在邻羟基偶氮苯化合物中N—H…O/O—H…N共振氢键普遍存在,O—H…N氢键强于N—H…O氢键,且N—H…O/O—H…N共振氢键的本质为三中心四电子的共价键模式。并对两个偶氮化合物a201和a202的单品结构进行了详细分析:这两个偶氮化合物分子在堆积成三维晶体时,主要依靠的是一些分子间弱相互作用,包括:C—H…O、C—H…N、C—H…Cl等弱氢键以及π…π堆积作用和C—H…π作用,并对类似的卤素取代偶氮苯分子进行了CSD检索分析。发现π…π堆积和C—H…π作用在这些分子中普遍存在着,它们的强度不大但却主导着分子的自组装过程。π…π堆积和C—H…π作用大多与对称中心相联系,属于中心对称的弱相互作用。此外,这类体系中还有大量的常规氢键存在,如C—H…O、C—H…N、C—H…X(Cl、Br)等,虽然是弱氢键但在分子自组装过程中也起重要作用。这些氢键大部分是与平移、螺旋轴和滑移面相联系的,属于非中心对称的氢键。这些数据与结论可以为非线性光学材料的设计提供重要的参考。
本文的第三章对4,4'-查尔酮化合物中的多中心C—H...O氢键进行了详细研究。从晶体结构的几何参数、量子化学的结构优化和能量计算以及量子拓扑学的电子密度分析三方面证明了此类化合物中R_3~1(11)型的C—H...O氢键的确存在。同时对β-羟基查尔酮和2'-羟基查尔酮化合物中的O—H...O共振氢键也进行了晶体化学、量子化学和量子拓扑学的详细研究。从几何构型、氢键强度和氢键性质等几个方面进行了讨论。证明在此类化合物中O—H...O共振氢键普遍存在,且O—H...O共振氢键的本质是三中心四电子的共价键模式。此外对氢键的距离、氢键临界点处的电子密度以及氢键能三者之间的线性相关性进行了量子拓扑学研究,结果表明这三者间存在比较好的线性相关性,同时也说明了键临界点处的电子密度等拓扑性质可以较好地表征氢键的强度和性质,AIM方法可以作为表征氢键等弱相互作用的直观有效的工具。
本文的第四章通过剑桥晶体结构数据库检索比较了27个苯乙烯吡啶盐中的C—H…π作用。这27个物质根据阴阳离子的种类分成四类,分别就其中的C—H…π、π…π作用的特点以及晶体堆积能、离子间相互作用能与中心对称晶体形成之间的相互关系进行了讨论。结果表明,阳离子相同时,若阴离子体积较大,由于有比较大的库仑力,有利于克服阳离子间的偶极相互作用,此时分子堆积为晶体时的空间群形式很大程度上取决于C—H…π、π…π等弱相互作用的连接方式。若这些弱相互作用以对称中心相联系,则堆积为中心对称的晶体;若阴离子体积较小,由于不能有效屏蔽阳离子的偶极效应,因此极易以中心对称的空间群堆积,但是若能引入分子内强氢键则有可能改变堆积方式。这些结论可以为非线性光学材料的设计提供参考。
Because of the vital role in the crystal engineering,the molecular recognition, supramolecular chemistry,the supramolecular assembly,crystal packing and the structure-activity relationship in biological systems,the study on the molecular weak interactions has attracted the attention of researchers.In recent years,the molecular weak interactions are being paid more attention to the experimental and theoretical investigations.But it is seldom about the weak interactions by topological analysis methods.
The purpose of this paper is to study the geometry configuration,bonding nature by quantum chemistry and topological analysis of the electronic density methods.The rules of the formation of molecular weak interactions were discussed in order to help the further research in this field.In this thesis,the four types of weak interactions such as conventional resonance-assisted hydrogen bond,non-conventional C—H…O hydrogen bond,C—H…πinteraction andπ…πstacking were studied.
At the first part of the thesis,the wide application of weak interaction,quantum chemistry and topological analysis was summarized.Bonding characters and electronic structures are still the main area of quantum chemical research.Because the topological analysis of the electronic density method is a new method,many studies are needed to be done by the theory.
In chapter two,the resonance-assisted N—H…O/O—H…N hydrogen bond in hydroxyl azobenzene were studied by crystal chemistry,quantum chemistry and topological analysis.The results lead us to the conclusion that the N—H…O hydrogen bond is stronger than O—H…N hydrogen bond in hydroxyl azobenzene,and this resonance-assisted hydrogen bond is best described as a 3-center,4-electron covalence bond.The structures of two azobenzene single crystals were also studied.The results show that the weak molecular interactions such as C—H…O、C—H…N、C—H…Cl hydrogen bond,π…πstacking and C—H…πinteraction play important role in crystal packing.The results of CSD(Cambridge Structural Database) searches also show thatπ…πstacking and C—H…πinteraction dominate the molecular assembly.π…πstacking and C—H…πinteractions are usually contacted by centrosymmetry,and C—H…O、C—H…N hydrogen bonds are noncentrosymmetric hydrogen bond.
In chapter three,the multi-center C—H...O hydrogen bond was studied.The geometry configuration,quantum calculation and electronic density analysis made us sure that R_3~1(11) multi-center C—H...O hydrogen bond was existed for a certainty in 4,4'-chalcone compounds.It was also testified that the characteristic of O—H...O resonance-assisted hydrogen bond was a 3-center,4-electron covalence bond.Linear correlations of the interaction energies with the electronic density in the hydrogen bond and the lengths of hydrogen bond were discussed.
In chapter four,the crystal structures of 27 stilbazolium salts were retrieved from CSD.The relationship among the characteristic ofπ…πstacking and C—H…πinteraction,crystal packing energies and formation of centrosymmetric crystal was discussed.The results indicated that when the stilbazolium salts have got the same cations,the large anions can provide strong electrostatic interactions to overcome the dipole-dipole interactions.In this condition,the connected methods of C—H…πandπ…πweak interactions will master the type of space group of crystal packing.If these weak interactions were connected by centrosymmetry,the compounds are accumulated in centrosymmetric space groups.The compounds will accumulated in centrosymmetric space groups if the volume of anions is not large enough to overcome dipole interactions.
引文
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