含杂环芳香烃体系分子间蓝移氢键的理论研究
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摘要
本工作运用量子化学从头算计算方法，以吡啶、呋喃、噻吩和吡咯等典型杂环芳香烃为质子受体，HCl、C_2H_2和HCX_3(X=F，Cl，Br，I)等典型分子为质子供体，比较系统地研究了它们之间形成分子间红移和蓝移氢键本质。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MP2，采用6-31G(d，p)，6-311+G(d，p)，6-311++G(d，p)，6-311++G(2df，2p)、AUG-cc-pVDZ基组研究了以吡啶为质子受体，HCl和HCCl_3为质子供体的分子间氢键。研究表明，在MP2／6-31G(d，p)水平下，吡啶与HCl分子之间仅形成了Cl—H...N氢键，分子间的氢键作用使Cl—H键伸长0.0495 (?)，振动频率减小了725.1cm~(-1)，表现为红移氢键。吡啶与HCCl_3间形成两种类型的氢键，在MP2／6-31G(d，p)水平下，C—H...N氢键使HCCl_3中的C—H键伸长0.0049 (?)，振动频率减小了79.1cm~(-1)，表现为红移氢键；而C—H...π相互作用使CHCl_3中的C—H键缩短0.003 (?)，振动频率增大了58 cm~(-1)，表现为蓝移氢键。所有这些氢键复合物中，不论是红移还是蓝移氢键，C—H或Cl—H的伸缩振动红外强度相对于单体来说都增大，且质子供体固有偶极矩导数都大于零。自然键轨道(NBO)分析表明，超共轭和重杂化理论以及Hobza等提出的观点都能很好的解释这些氢键的形成原因。包含电子相关的Hartree-Fock理论能很好的解释复合物形成分子间C—H...N氢键本质。
2．运用量子化学从头算方法研究了复合物C_5H_5N...HCX_3(X=F，Cl，Br，I)分子间C—H...N和C—H...π氢键。研究表明，在MP2／SDD水平下，分子间C—H...N氢键的形成均使HCX_3分子中C—H键伸长，伸缩振动频率减小，形成红移氢键；分子间C—H...π氢键的形成均使HCX_3分子中C—H键收缩，伸缩振动频率增大，形成蓝移氢键。振动光谱分析表明，不能根据质子供体分子HCX_3的固有偶极矩对C—H键长的导数来判断红移氢键和蓝移氢键。NBO分析表明，超共轭效应占优势，因此形成C—H...N红移氢键；重杂化效应占优势，因此形成C—H...π蓝移氢键。
3．用量子化学从头算(ab initio)方法MP2，分别在B3LYP／6-311++G(d，p)，MP2／6-31G(d，p)，MP2／6-31+G(d，p)，MP2／6-311++G(d，p)理论水平下对以呋喃、噻吩、吡咯和吡啶为质子受体，氟仿和乙炔为质子供体的C—H...π型氢键复合物进行了研究。计算表明：当以氟仿为质子供体时，所形成的C—H...π型氢键均为蓝移氢键，表现为C—H键收缩，而以乙炔为质子供体时，所形成的C—H...π型氢键均为红移氢键，表现为C—H键伸长。自然键轨道(NBO)分析表明，影响氢键红移和氢键蓝移主要有三个因素：π→σ~*(C—H)超共轭作用、C—H键轨道再杂化和质子供体电子密度重排。其中，超共轭作用属于键伸长效应，电子密度重排和轨道再杂化属于键收缩效应。在以乙炔为质子供体复合物中，由于键伸长效应处于优势地位导致形成红移氢键；在以氟仿为质子供体的复合物中，由于键收缩效应处于优势地位导致形成蓝移氢键。
In present paper, ab initio quantum mechanics method is employed to investigate the origin of red-shifting and blue-shifting hydrogen bond between furan, thiophene, pyrole, pyridine and HCl, C_2H_2, HCX_3(X=F, Cl, Br, I). The main contents are the following:
1. The hydrogen bonds of HCl and HCCl_3 as the proton donors with pyridine as the acceptor were studied at the MP2 level of theory using the five basis sets 6-31G(d,p), 6-311+G(d,p), 6-311++G(d,p), 6-311++G(2df,2p) and AUG-cc-pVDZ. Pyridine and HCl can only form a Cl—H...N H-bond, which causes a large frequency red shift of 725 cm~(-1) for the Cl—H vibration and an elongation 0.0495 A of this bond using the basis set 6-31G(d,p). Two H-bonds are formed between pyridine and HCCl_3: the C—H...N hydrogen bond with an elongation 0.0049 A of the C—H bond and a red shift of 80 cm~(-1) for the C—H stretch vibration of HCCl_3, and the C—H...πinteraction with a contraction 0.003 A of the C—H bond and a blue shift of 58 cm~(-1) for the C—H stretch vibration of HCCl_3 using the basis set 6-31G(d,p). In these H-bonds, regardless of which are red-shifted or blue-shifted, the IR intensities of the C—H and Cl—H stretch vibrations increase, and the permanent dipole moment derivatives of the proton donors are positive. The natural bond orbital analysis was carried out, and the concepts of hyperconjugation and rehybridization and the theory of Hobza were applied to account for the origin of these hydrogen bonds. A post Hartree-Fock wavefunction containing electron correlation in the analysis of the natural bond orbital is required for interpreting the C—H...N H-bond in pyridine—HCCl_3.
2. The C—H...N and C—H...πinteraction between pyridine and HCX_3(X=F, Cl,Br, I) was investigated by means of quantum chemical method of high level ab initio calculations. For the C—H...N interaction classical H-bonds are formed with an elongation of C—H and a red shift. However, for the C—H...πinteraction blue shifting H-bonds are identified with a contraction of C—H and a blue shift. The result of vibrational spectral analysis indicates that it is impossible to confirm blue shifting or red shifting H-bonds by the derivative of permanent dipole moment with respect to C—H stretch of the proton donor only. The NBO analysis show that the competitions of hyperconjugation and rehybridization result in two kinds of H-bonds.
3. Ab initio quantum mechanics method is employed to investigate intermolecular interactions between furan, thiophene, pyrole and pyridine as proton acceptor and acetylene and trifluoromethane at B3LYP/6-311++G(d, p), MP2/6-31G(d, p), MP2/6-31+G(d, p), MP2/6-311++G(d, p) levels. For compounds containing acetylene C—H...πred shifting H-bond is formed with C—H bond elongation and a concomitant red shift. However, for compounds containing trifluoromethane, C—H...πblue shifting H-bond is formed with C—H bond contraction and concomitant blue shift. The NBO analysis shows that the C—H bond length in C—H...πis controlled by a balance of three main factors. C—H bond lengthening due toπ→σ*(C—H) hyperconjugative interaction is balanced by C—H bond shortening due to increase of s-character and polarization of the C—H bond and redistribution of electron density in proton donor. In compounds containing acetylene, hyperconjugative interaction dominates which results in red shifting H-bonds. In compounds containing trifluoromethane, the condition is reverse which results in blue shifting H-bonds.
1．用量子化学从头算(ab initio)方法MP2，采用6-31G(d，p)，6-311+G(d，p)，6-311++G(d，p)，6-311++G(2df，2p)、AUG-cc-pVDZ基组研究了以吡啶为质子受体，HCl和HCCl_3为质子供体的分子间氢键。研究表明，在MP2／6-31G(d，p)水平下，吡啶与HCl分子之间仅形成了Cl—H...N氢键，分子间的氢键作用使Cl—H键伸长0.0495 (?)，振动频率减小了725.1cm~(-1)，表现为红移氢键。吡啶与HCCl_3间形成两种类型的氢键，在MP2／6-31G(d，p)水平下，C—H...N氢键使HCCl_3中的C—H键伸长0.0049 (?)，振动频率减小了79.1cm~(-1)，表现为红移氢键；而C—H...π相互作用使CHCl_3中的C—H键缩短0.003 (?)，振动频率增大了58 cm~(-1)，表现为蓝移氢键。所有这些氢键复合物中，不论是红移还是蓝移氢键，C—H或Cl—H的伸缩振动红外强度相对于单体来说都增大，且质子供体固有偶极矩导数都大于零。自然键轨道(NBO)分析表明，超共轭和重杂化理论以及Hobza等提出的观点都能很好的解释这些氢键的形成原因。包含电子相关的Hartree-Fock理论能很好的解释复合物形成分子间C—H...N氢键本质。
2．运用量子化学从头算方法研究了复合物C_5H_5N...HCX_3(X=F，Cl，Br，I)分子间C—H...N和C—H...π氢键。研究表明，在MP2／SDD水平下，分子间C—H...N氢键的形成均使HCX_3分子中C—H键伸长，伸缩振动频率减小，形成红移氢键；分子间C—H...π氢键的形成均使HCX_3分子中C—H键收缩，伸缩振动频率增大，形成蓝移氢键。振动光谱分析表明，不能根据质子供体分子HCX_3的固有偶极矩对C—H键长的导数来判断红移氢键和蓝移氢键。NBO分析表明，超共轭效应占优势，因此形成C—H...N红移氢键；重杂化效应占优势，因此形成C—H...π蓝移氢键。
3．用量子化学从头算(ab initio)方法MP2，分别在B3LYP／6-311++G(d，p)，MP2／6-31G(d，p)，MP2／6-31+G(d，p)，MP2／6-311++G(d，p)理论水平下对以呋喃、噻吩、吡咯和吡啶为质子受体，氟仿和乙炔为质子供体的C—H...π型氢键复合物进行了研究。计算表明：当以氟仿为质子供体时，所形成的C—H...π型氢键均为蓝移氢键，表现为C—H键收缩，而以乙炔为质子供体时，所形成的C—H...π型氢键均为红移氢键，表现为C—H键伸长。自然键轨道(NBO)分析表明，影响氢键红移和氢键蓝移主要有三个因素：π→σ~*(C—H)超共轭作用、C—H键轨道再杂化和质子供体电子密度重排。其中，超共轭作用属于键伸长效应，电子密度重排和轨道再杂化属于键收缩效应。在以乙炔为质子供体复合物中，由于键伸长效应处于优势地位导致形成红移氢键；在以氟仿为质子供体的复合物中，由于键收缩效应处于优势地位导致形成蓝移氢键。
In present paper, ab initio quantum mechanics method is employed to investigate the origin of red-shifting and blue-shifting hydrogen bond between furan, thiophene, pyrole, pyridine and HCl, C_2H_2, HCX_3(X=F, Cl, Br, I). The main contents are the following:
1. The hydrogen bonds of HCl and HCCl_3 as the proton donors with pyridine as the acceptor were studied at the MP2 level of theory using the five basis sets 6-31G(d,p), 6-311+G(d,p), 6-311++G(d,p), 6-311++G(2df,2p) and AUG-cc-pVDZ. Pyridine and HCl can only form a Cl—H...N H-bond, which causes a large frequency red shift of 725 cm~(-1) for the Cl—H vibration and an elongation 0.0495 A of this bond using the basis set 6-31G(d,p). Two H-bonds are formed between pyridine and HCCl_3: the C—H...N hydrogen bond with an elongation 0.0049 A of the C—H bond and a red shift of 80 cm~(-1) for the C—H stretch vibration of HCCl_3, and the C—H...πinteraction with a contraction 0.003 A of the C—H bond and a blue shift of 58 cm~(-1) for the C—H stretch vibration of HCCl_3 using the basis set 6-31G(d,p). In these H-bonds, regardless of which are red-shifted or blue-shifted, the IR intensities of the C—H and Cl—H stretch vibrations increase, and the permanent dipole moment derivatives of the proton donors are positive. The natural bond orbital analysis was carried out, and the concepts of hyperconjugation and rehybridization and the theory of Hobza were applied to account for the origin of these hydrogen bonds. A post Hartree-Fock wavefunction containing electron correlation in the analysis of the natural bond orbital is required for interpreting the C—H...N H-bond in pyridine—HCCl_3.
2. The C—H...N and C—H...πinteraction between pyridine and HCX_3(X=F, Cl,Br, I) was investigated by means of quantum chemical method of high level ab initio calculations. For the C—H...N interaction classical H-bonds are formed with an elongation of C—H and a red shift. However, for the C—H...πinteraction blue shifting H-bonds are identified with a contraction of C—H and a blue shift. The result of vibrational spectral analysis indicates that it is impossible to confirm blue shifting or red shifting H-bonds by the derivative of permanent dipole moment with respect to C—H stretch of the proton donor only. The NBO analysis show that the competitions of hyperconjugation and rehybridization result in two kinds of H-bonds.
3. Ab initio quantum mechanics method is employed to investigate intermolecular interactions between furan, thiophene, pyrole and pyridine as proton acceptor and acetylene and trifluoromethane at B3LYP/6-311++G(d, p), MP2/6-31G(d, p), MP2/6-31+G(d, p), MP2/6-311++G(d, p) levels. For compounds containing acetylene C—H...πred shifting H-bond is formed with C—H bond elongation and a concomitant red shift. However, for compounds containing trifluoromethane, C—H...πblue shifting H-bond is formed with C—H bond contraction and concomitant blue shift. The NBO analysis shows that the C—H bond length in C—H...πis controlled by a balance of three main factors. C—H bond lengthening due toπ→σ*(C—H) hyperconjugative interaction is balanced by C—H bond shortening due to increase of s-character and polarization of the C—H bond and redistribution of electron density in proton donor. In compounds containing acetylene, hyperconjugative interaction dominates which results in red shifting H-bonds. In compounds containing trifluoromethane, the condition is reverse which results in blue shifting H-bonds.
引文
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[1] Stefov V., Pejov L., Loptrajanov B., Experimental and quantum chemical study of pyrrole self-association through N-H...π hydrogen bonding. J. Mol. Struct., 2003, 649, 231-243.
[2] Wang B. Q., Li Z. R., Wu D., Single-electron hydrogen bonds in the methyl radical complexes H_3C...HF and H_3C...HCCH: an ab initio study. Chem. Phys. Lett., 2003, 375, 91-95.
[3] Hobza P., Havlas Z., Blue-Shifting Hydrogen Bonds. Chem. Rev., 2000, 100, 4253-4264.
[4] 吴迪，李志儒，郑植仁，CH_2F_2…H_2O中强π型二级氢键．高等学校化学学报，2002，23，640-643．
[5] Karpfen Alfred., Kryachko E. S., Blue-shifted hydrogen-bonded complexes: CH_3F...(HF)_1≤_n≤_3 and CH_2F_2...(HF)_1≤_n≤_3. Chem. Phys., 2005, 310, 77-84.
[6] Rutkowski K. S., Rodziewicz P., Melikova S. M. et al., Blue shifted F_3CH...FCD_3 and Cl_3CH...FCD_3 weakly H-bound complexes, Cryospectroscopic and ab initio study. Chem. Phys., 2005, 313, 225-243.
[7] McDowell S. A. C. Blue and red shifts in F_3C-H... B (B=FH, C1H, OH_2, SH_2 and Cl~-) complexes predicted by a pertttrbative model. Chem. Phys. Lett., 2006, 424, 239-242.
[8] 杨颐，张为俊，裴世鑫，等．N-H…O红移氢键和蓝移氢键的理论研究．中国科学B辑，2006，36，218-226．
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[10] Lu P., Liu G. Q., Li J. C. Existing problems in theoretical determination of red-shifted or blue-shifted hydrogen bond. J. Mol. Struct. (THEOCHEM), 2005, 723, 95-100.
[11] Hobza P., Havlas Z. Improper, blue-shifting hydrogen bond. Theor. Chem. Acc., 2002, 108, 325-334.
[12] Masunov A., Dannenberg J. J. C-H Bond, Shortening upon Hydrogen Bond Formation: Influence of an Electric Field. J. Phys. Chem. A., 2001, 105, 4737-4740.
[13] Steve S., Tapas K. Red-versus Blue-Shifting Hydrogen Bonds: Are There Fundamental Distinctions? J. Phys. Chem. A., 2002, 106, 1784-1789.
[14] Zierkiewicz W., Jurecka P. Hobza P. On Differences between Hydrogen Bonding and Improper Blue-Shifting Hydrogen Bonding. ChemPhysChem., 2005, 6, 609-617.
[15] Alabugin I. V., Manoharan M., Peabody S., et al. Electronic Basis of Improper Hydrogen Bonding: A Subtle Balance of Hyperconjugation and Rehybridization. J. Am. Chem. Soc., 2003, 125, 5973-5987.
[16] Li A. Y. Theoretical Investigation of Hydrogen Bonds between CO and HNF_2, H_2NF and HNO. J. Phys. Chem. A., 2006, 110, 10805-10816.
[17] Sutton L. E., Powell H. M. Tables of Interatomic Distance and Configuration in Molecules and Ions, London: The Chemical Society, 1965.
[18] 史福强，安静仪，李文，等．吡咯与HCl和CHCl3分子间Cl(C)—H...π型氢键的理论研究．化学学报，2004，62，1171-1175．
[19] 李绛，谢代前，鄢国森，呋喃与HCl和CHCl_3构成的分子间氢键的理论研究．中国科学B辑，2003，33，21-25．
[20] Hermansson K. J. Blue-Shifting Hydrogen Bonds. J. Phys. Chem. A., 2002, 106, 4695-4702.
[21] McDowell S. A. C. Blue-shifting hydrogen bonding in the N_2…HArCl dimmer. J. Mol. Struct. (THEOCHEM), 2003, 625, 243-250.
[22] McDowell S. A. C. A computational study of the dihydrogen bonded complexes HBeH...HArF and HBeH...HKrF. J. Chem. Phys., 2004, 121, 5728-5733.
[23] McDowell S. A. C. A computational study of the CO...HHeF dimmer. J. Mol. Struct. (THEOCHEM), 2004, 674, 227-232.
[1] 黎新，谷氨酸热分解机理的研究．西南师范大学学报，1999，24，438-442．
[2] 李道华，邻二氮杂苯-水复合物氢键结构的理论研究．四川师范大学学报，2004，27，642-644．
[3] Scheiner S., Hydrogen Bonding. New York, Oxford University Press, 1997.
[4] Hobza P., Havlas Z., Improper, blue-shifting hydrogen bond. Theor. Chem. Acc., 2002, 108, 325-334.
[5] Hobza P., Spirko V., Selzle H L., et al., Anti-Hydrogen Bond in the Benzene Dimer and Other Carbon Proton Donor Complexes. J. Phys. Chem. A, 1998, 102, 2501-2504.
[6] Hobza P., Havlas Z. Blue-shifting hydrogen bonds. Chem. Rev., 2000, 100, 4253-4264.
[7] Zierkiewicz W., Jurecka P., Hobza P., On Differences between Hydrogen bonding and improper Blue-shifting Hydrogen Bonding. ChemPhysChem, 2005, 6, 609-617
[8] Zierkiewicz W., Michalska D., Havlas Z., et al. Study of the Nature of Improper Blue-Shifting Hydrogen Bonding and Standard Hydrogen Bonding in X_3CH...OH_2 and XH...OH_2 Complexes(X=F, Cl, Br, I): A Correlated Ab Initio Study. ChemPhysChem, 2002, 3, 511-518.
[9] Wang X., Zhou G., Tian A. M., et al., Ab initio investigation on blue shift and red shift of C-H stretching vibrational frequency in NH_3...CH_nX_(4-n)(n=1,3,X=F,Cl,Br, I) complexes. J. Mol. Struct. (THEOCHEM), 2005, 718, 1-7.
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[1] G.R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989.
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[27] Alabugin I. V., Manoharan M., Peabody S., et al. Electronic Basis of Improper Hydrogen Bonding: A Subtle Balance of Hyperconjugation and Rehybridization. J. Am. Chem. Soc., 2003, 125, 5973-5987.
[28] Zierkiewicz W., Jurecka P., Hobza P. On Differences between Hydrogen bonding and improper Blue-shifting Hydrogen Bonding. ChemPhysChem., 2005, 6, 609-617.
[29] Zierkiewicz W., Michalska D., Havlas Z., et al. Study of the Nature of Improper Blue-Shifting Hydrogen Bonding and Standard Hydrogen Bonding in the X_3CH...OH_2 and XH...OH_2 Complexes(X=F,Cl,Br,I): A Correlated Ab Initio Study. ChemPhysChem., 2002, 3, 511-518.
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[1] Stefov V., Pejov L., Loptrajanov B., Experimental and quantum chemical study of pyrrole self-association through N-H...π hydrogen bonding. J. Mol. Struct., 2003, 649, 231-243.
[2] Wang B. Q., Li Z. R., Wu D., Single-electron hydrogen bonds in the methyl radical complexes H_3C...HF and H_3C...HCCH: an ab initio study. Chem. Phys. Lett., 2003, 375, 91-95.
[3] Hobza P., Havlas Z., Blue-Shifting Hydrogen Bonds. Chem. Rev., 2000, 100, 4253-4264.
[4] 吴迪，李志儒，郑植仁，CH_2F_2…H_2O中强π型二级氢键．高等学校化学学报，2002，23，640-643．
[5] Karpfen Alfred., Kryachko E. S., Blue-shifted hydrogen-bonded complexes: CH_3F...(HF)_1≤_n≤_3 and CH_2F_2...(HF)_1≤_n≤_3. Chem. Phys., 2005, 310, 77-84.
[6] Rutkowski K. S., Rodziewicz P., Melikova S. M. et al., Blue shifted F_3CH...FCD_3 and Cl_3CH...FCD_3 weakly H-bound complexes, Cryospectroscopic and ab initio study. Chem. Phys., 2005, 313, 225-243.
[7] McDowell S. A. C. Blue and red shifts in F_3C-H... B (B=FH, C1H, OH_2, SH_2 and Cl~-) complexes predicted by a pertttrbative model. Chem. Phys. Lett., 2006, 424, 239-242.
[8] 杨颐，张为俊，裴世鑫，等．N-H…O红移氢键和蓝移氢键的理论研究．中国科学B辑，2006，36，218-226．
[9] Feng Y., Zhao S. W., Liu L., et al. Blue-shifted dihydrogen bonds. J. Phys. Org. Chem., 2004, 17, 1099-1106.
[10] Lu P., Liu G. Q., Li J. C. Existing problems in theoretical determination of red-shifted or blue-shifted hydrogen bond. J. Mol. Struct. (THEOCHEM), 2005, 723, 95-100.
[11] Hobza P., Havlas Z. Improper, blue-shifting hydrogen bond. Theor. Chem. Acc., 2002, 108, 325-334.
[12] Masunov A., Dannenberg J. J. C-H Bond, Shortening upon Hydrogen Bond Formation: Influence of an Electric Field. J. Phys. Chem. A., 2001, 105, 4737-4740.
[13] Steve S., Tapas K. Red-versus Blue-Shifting Hydrogen Bonds: Are There Fundamental Distinctions? J. Phys. Chem. A., 2002, 106, 1784-1789.
[14] Zierkiewicz W., Jurecka P. Hobza P. On Differences between Hydrogen Bonding and Improper Blue-Shifting Hydrogen Bonding. ChemPhysChem., 2005, 6, 609-617.
[15] Alabugin I. V., Manoharan M., Peabody S., et al. Electronic Basis of Improper Hydrogen Bonding: A Subtle Balance of Hyperconjugation and Rehybridization. J. Am. Chem. Soc., 2003, 125, 5973-5987.
[16] Li A. Y. Theoretical Investigation of Hydrogen Bonds between CO and HNF_2, H_2NF and HNO. J. Phys. Chem. A., 2006, 110, 10805-10816.
[17] Sutton L. E., Powell H. M. Tables of Interatomic Distance and Configuration in Molecules and Ions, London: The Chemical Society, 1965.
[18] 史福强，安静仪，李文，等．吡咯与HCl和CHCl3分子间Cl(C)—H...π型氢键的理论研究．化学学报，2004，62，1171-1175．
[19] 李绛，谢代前，鄢国森，呋喃与HCl和CHCl_3构成的分子间氢键的理论研究．中国科学B辑，2003，33，21-25．
[20] Hermansson K. J. Blue-Shifting Hydrogen Bonds. J. Phys. Chem. A., 2002, 106, 4695-4702.
[21] McDowell S. A. C. Blue-shifting hydrogen bonding in the N_2…HArCl dimmer. J. Mol. Struct. (THEOCHEM), 2003, 625, 243-250.
[22] McDowell S. A. C. A computational study of the dihydrogen bonded complexes HBeH...HArF and HBeH...HKrF. J. Chem. Phys., 2004, 121, 5728-5733.
[23] McDowell S. A. C. A computational study of the CO...HHeF dimmer. J. Mol. Struct. (THEOCHEM), 2004, 674, 227-232.
[1] 黎新，谷氨酸热分解机理的研究．西南师范大学学报，1999，24，438-442．
[2] 李道华，邻二氮杂苯-水复合物氢键结构的理论研究．四川师范大学学报，2004，27，642-644．
[3] Scheiner S., Hydrogen Bonding. New York, Oxford University Press, 1997.
[4] Hobza P., Havlas Z., Improper, blue-shifting hydrogen bond. Theor. Chem. Acc., 2002, 108, 325-334.
[5] Hobza P., Spirko V., Selzle H L., et al., Anti-Hydrogen Bond in the Benzene Dimer and Other Carbon Proton Donor Complexes. J. Phys. Chem. A, 1998, 102, 2501-2504.
[6] Hobza P., Havlas Z. Blue-shifting hydrogen bonds. Chem. Rev., 2000, 100, 4253-4264.
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