杂环芳香体系分子间氢键和双氢键的理论研究
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摘要
本课题运用量子化学从头算计算方法,以无机苯和吡啶等典型无机物与杂环芳香烃为质子受体(成双氢键时同时也为质子供体),H_xCF_(4-x)(x=1～3)、HX、HCX_3(X=F,Cl,Br)、H_2O、CH_3COOH和CH_3OH等典型分子为质子供体(成双氢键时同时也为质子受体),比较系统地研究了它们之间形成分子间氢键和双氢键本质。本论文主要包括以下三部分:
1.用量子化学从头算(ab initio)方法B3LYP采用6-31G(d,p)、6-311+G(d,p)、6-311++G(d,p)、6-311++G(2df,2p)、AUG-cc-pVDZ和AUG-cc-pVTZ基组研究了无机苯与氟代甲烷H_xCF_(4-x)(x=1～3)形成的分子间双氢键B-H…H-C和传统氢键N-H…F。研究表明,分子间的双氢键作用使BH键键长增大与伸缩振动频率红移,以及使CH键键长减短与伸缩振动频率蓝移;而传统氢键的作用使NH键键长增大与伸缩振动频率红移。电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征,自然键轨道分析表明分子内与分子间超共轭和重杂化理论可以解释这些氢键的形成机制。
2.运用量子化学从头算方法MP2,采用6-311+G(d,p)、6-311++G(d,p)与AUG-cc-pVDZ研究了无机苯与HF、HCl和H_2O分子之间形成的双氢键B-H…H-X和传统氢键N-H…X与X-H…X(X=F,Cl,O)。研究表明,双氢键作用使B-H与H-X键长增大与伸缩振动频率红移;而传统氢键的作用使N-H和H-X键长增大与频率红移。电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征。自然键轨道分析表明超共轭和重杂化理论可以解释这些双氢键和氢键的形成机制。
3.用量子化学从头算(ab initio)方法B3LYP方法,6-311++G(d,p)、6-311++G(2df,2p)与AUG-cc-pVDZ理论水平下,吡啶可以用其C-H作为质子给体形成C-H…Y氢键,也可以用N原子作为质子接受体形成的N…H-X氢键。本文从理论上研究了吡啶同时作为质子给体和质子接受体与HOCNH_2、CH_3CONH_2、HCOOH、CH_3COOH、HCHO和CH_3CHO形成的C-H…O和N…H-X(X=N,O,C)两种氢键。分析了它们的频率位移特征,N…X-H(X=N,O,C)传统氢键的形成导致相关的X-H键键长增大,振动频率减小发生红移;与C-H…O传统氢键的形成导致相关的C-H键蓝移。且同一体系中N…X-H(X=N,O,C)传统氢键较强,电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征。自然键轨道分析表明超共轭和重杂化理论可以解释这些双氢键和氢键的形成机制。
In the present paper,ab initio quantum mechanics method is employed to investigate the origin of hydrogen bonds and dihydrongen bonds between borazine,pyridine and H_xCF_(4-x)(x=1～3)、HX、HCX_3(X=F,Cl,Br),H_2O,CH_3COOH and CH_3OH.The main contents are the following:
1.The dihydrogen Bonds B-H…H-C and traditional H-bonds N-H…F between B_3N_3H_6 and H_xCF_(4-x)(x=1～3) have been theoretically studied by use of the density functional theory in the level of B3LYP/6-31G(d,p)、6-311+G(d,p)、6-311++G (d,p)、6-311++G(2df,2p)、AUG-cc-pVDZ、AUG-cc-pVTZ.We found that upon formation of the dihydrogen Bonds the BH bonds are red-shifted and the CH bonds are blue-shifts,and that the formation of the traditional H-bonds cause the NH bonds red-shifted.The topological properties of the complexes show that these intermolecular interactions are indeed H-bonds.The natural bond orbital analysis shows that these H-bonds can be interpreted by use of the theory of inter- and intra-molecular hyperconjugation and rehybridization.
2.The dihydrogen bonds B-H…H-X and traditional H-bonds N-H…X and X-H…X(X=F,Cl,O) between B_3N_3H_6 and HF、HCl and H_2O have been theoretically studied by use of the ab initio quantum mechanics method(MP2).We found that upon formation of the dihydrogen Bonds,the BH bonds and HX bond are red-shifted,and that the formation of the traditional H-bonds causes the NH and HX bonds red-shifted. The topological properties of the complexes show that these intermolecular interactions are indeed H-bonds.The natural bond orbital analysis shows that these H-bonds can be interpreted by use of the theory of hyperconjugation and rehybridization.
3.The N…H-X(X=N,O,C) and C-H…O interaction between pyridine and HOCNH_2、CH_3CONH2、HCOOH、CH_3COOH et al.was investigated by means of quantum chemical method of Becke 3-parameter hybrid exchange functionals and Lee-Young-Parr correlation functionals of DFT in the level of 6-311++G(d,p)、6-311++G(2df,2p) and AUG-cc-pVDZ.For the N…H-X(X=N,O,C) interaction classical H-bonds are formed with an elongation of C-H and a red shift.However,for the C-H…O interaction blue shifting H-bonds are identified with a contraction of C-H and a blue shift.We found that H-X(X=N,O,C) bonds are stronger than C-H bonds.The NBO analysis show that the competitions of hyperconjugation and rehybridization result in two kinds of H-bonds.
1.用量子化学从头算(ab initio)方法B3LYP采用6-31G(d,p)、6-311+G(d,p)、6-311++G(d,p)、6-311++G(2df,2p)、AUG-cc-pVDZ和AUG-cc-pVTZ基组研究了无机苯与氟代甲烷H_xCF_(4-x)(x=1～3)形成的分子间双氢键B-H…H-C和传统氢键N-H…F。研究表明,分子间的双氢键作用使BH键键长增大与伸缩振动频率红移,以及使CH键键长减短与伸缩振动频率蓝移;而传统氢键的作用使NH键键长增大与伸缩振动频率红移。电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征,自然键轨道分析表明分子内与分子间超共轭和重杂化理论可以解释这些氢键的形成机制。
2.运用量子化学从头算方法MP2,采用6-311+G(d,p)、6-311++G(d,p)与AUG-cc-pVDZ研究了无机苯与HF、HCl和H_2O分子之间形成的双氢键B-H…H-X和传统氢键N-H…X与X-H…X(X=F,Cl,O)。研究表明,双氢键作用使B-H与H-X键长增大与伸缩振动频率红移;而传统氢键的作用使N-H和H-X键长增大与频率红移。电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征。自然键轨道分析表明超共轭和重杂化理论可以解释这些双氢键和氢键的形成机制。
3.用量子化学从头算(ab initio)方法B3LYP方法,6-311++G(d,p)、6-311++G(2df,2p)与AUG-cc-pVDZ理论水平下,吡啶可以用其C-H作为质子给体形成C-H…Y氢键,也可以用N原子作为质子接受体形成的N…H-X氢键。本文从理论上研究了吡啶同时作为质子给体和质子接受体与HOCNH_2、CH_3CONH_2、HCOOH、CH_3COOH、HCHO和CH_3CHO形成的C-H…O和N…H-X(X=N,O,C)两种氢键。分析了它们的频率位移特征,N…X-H(X=N,O,C)传统氢键的形成导致相关的X-H键键长增大,振动频率减小发生红移;与C-H…O传统氢键的形成导致相关的C-H键蓝移。且同一体系中N…X-H(X=N,O,C)传统氢键较强,电子密度拓扑性质分析表明这些相互作用具有氢键的基本特征。自然键轨道分析表明超共轭和重杂化理论可以解释这些双氢键和氢键的形成机制。
In the present paper,ab initio quantum mechanics method is employed to investigate the origin of hydrogen bonds and dihydrongen bonds between borazine,pyridine and H_xCF_(4-x)(x=1～3)、HX、HCX_3(X=F,Cl,Br),H_2O,CH_3COOH and CH_3OH.The main contents are the following:
1.The dihydrogen Bonds B-H…H-C and traditional H-bonds N-H…F between B_3N_3H_6 and H_xCF_(4-x)(x=1～3) have been theoretically studied by use of the density functional theory in the level of B3LYP/6-31G(d,p)、6-311+G(d,p)、6-311++G (d,p)、6-311++G(2df,2p)、AUG-cc-pVDZ、AUG-cc-pVTZ.We found that upon formation of the dihydrogen Bonds the BH bonds are red-shifted and the CH bonds are blue-shifts,and that the formation of the traditional H-bonds cause the NH bonds red-shifted.The topological properties of the complexes show that these intermolecular interactions are indeed H-bonds.The natural bond orbital analysis shows that these H-bonds can be interpreted by use of the theory of inter- and intra-molecular hyperconjugation and rehybridization.
2.The dihydrogen bonds B-H…H-X and traditional H-bonds N-H…X and X-H…X(X=F,Cl,O) between B_3N_3H_6 and HF、HCl and H_2O have been theoretically studied by use of the ab initio quantum mechanics method(MP2).We found that upon formation of the dihydrogen Bonds,the BH bonds and HX bond are red-shifted,and that the formation of the traditional H-bonds causes the NH and HX bonds red-shifted. The topological properties of the complexes show that these intermolecular interactions are indeed H-bonds.The natural bond orbital analysis shows that these H-bonds can be interpreted by use of the theory of hyperconjugation and rehybridization.
3.The N…H-X(X=N,O,C) and C-H…O interaction between pyridine and HOCNH_2、CH_3CONH2、HCOOH、CH_3COOH et al.was investigated by means of quantum chemical method of Becke 3-parameter hybrid exchange functionals and Lee-Young-Parr correlation functionals of DFT in the level of 6-311++G(d,p)、6-311++G(2df,2p) and AUG-cc-pVDZ.For the N…H-X(X=N,O,C) interaction classical H-bonds are formed with an elongation of C-H and a red shift.However,for the C-H…O interaction blue shifting H-bonds are identified with a contraction of C-H and a blue shift.We found that H-X(X=N,O,C) bonds are stronger than C-H bonds.The NBO analysis show that the competitions of hyperconjugation and rehybridization result in two kinds of H-bonds.
引文
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[1]Domagala M,Grabowski S J.C-H…N and C-H…S Hydrogen BondssInfluence of Hybridization on Their Strength[J].J Phys Chem,2005,109:5683-5688.
[2]An Yong Li,Su Wen Wang.Ab initio investigation of hydrogen bonds between pyridine and HCl,CHCl_3[J].J Mol Struct,2007,807:191-199.
[3]黎安勇,闫秀花,王素纹.三接触弯曲构型的监移氢键CH_3…Y的理论研究[J].化学学报, 2007,24:2809-2816.
[4]王海燕,曾艳丽,郑世钧,等.吡咯与一系列小分子之间的双氢键[J].物理化学学报,2007,23(7):1131-1135.
[5]Hobza P,HavlasZ.Blue-shifted Hydrogen bonds[J].Chem Rev,2000,100(11):4253-4264.
[6]An Yong Li,Yan X H.Electronic Properties of Multifurcated Bent Hydrogen Bonds CH_3…Y and CH_2…Y[J].Phys Chem Chem Phys,2007,9:6263-6271.
[7]Daniel Benker,Thomas M.Klapotke.An ab initio Valence Bond(VB) Calculation of the πDelocalization Energy in Borazine,B_3N_3H_6[J].Heteroatom Chem,2005,16:311-315.
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