方酸与2, 6-二苯并咪唑的超分子自组装及氢键实验与理论研究

doi:10.3866/PKU.WHXB201512252

Abstract

Abstract:

Supramolecular complex (1) was obtained from a mixture of squaric acid and 2, 6-bis(2-benzimidazolyl)pyridine in deuterated dimethylsulfoxide (d-DMSO) and characterized by single-crystal X-ray diffraction. The crystal structure data showed that 1 was a one-dimensional chain polymer assembled through π-π stacking and hydrogen bonding interactions. Infrared vibrational spectra of 1 were measured at different temperatures and sample concentrations in carbon tetrachloride. Moreover, the hydrogen bonding in the crystals was further evaluated by density functional theory (DFT) and atoms in molecules (AIM) theory. The calculated hydrogen bonding energies were about 135.65 and 49.40 J·mol^-1, respectively.

Key words: Intermolecular hydrogen bonding, Variable temperature infrared, Density functional theory, Atoms in molecules theory

MSC2000:

O641

Ai-Bin HU,Zhi-Quan PAN,Qing-Rong CHENG,Hong ZHOU. Experimental and Theoretical Evidence for Supramolecular Self-Assembly and Hydrogen Bonding between Squaric Acid and 2, 6-Bis(2-benzimidazolyl)pyridine[J].Acta Phys. -Chim. Sin., 2016, 32(3): 665-670.

References

1	Majerz I. J. Phys. Chem. A 2012, 116 (30), 7992.
2	Jeffrey G. A. ; Saenger W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin 1991.
3	Scheiner S. Hydrogen Bonding: a Theoretical Perspective;Oxford University Press: New York 1997.
4	Ebrahimi A. ; Habibi Khorassani S. M. ; Delarami H. Chemical Physics 2009, 365 (1-2), 18.
5	Herrebout W. A. ; Clou K. ; Desseyn H. O. J. J. Phys. Chem. A 2001, 105 (20), 4865.
6	Tonan K. ; Ikawa S. I. J. Am. Chem. Soc. 1996, 118 (29), 6960.
7	Koch U. ; Popelier P. L. A. J. Phys. Chem. 1995, 99 (24), 9747.
8	Bader R. F.W. Chem. Rev. 1991, 91 (5), 893.
9	Bader R. F.W. Atoms in Molecules a Quantum Theory;Clarendon Press: Oxford 1994.
10	Ranganathan A. ; Kulkarni G. U. ; Rao C. N. R. J. Phys. Chem. A 2003, 107 (31), 6073.
11	Takasu I. ; Izuoka A. ; Sugawara T. J. Phys. Chem. B 2004, 108 (18), 5527.
12	dos Reis F. D. ; Gatti I. C. ; Garcia H. C. ; de Oliveira V. E. ; de Oliveira L. F. C. J. Phys. Chem. A 2014, 118 (49), 11521.
13	Smart and Saint, Area Detector Controland Integration Software; Simens Analytical XSystems, Inc.: Madison, WI, USA, 1996.
14	Sheldrick G. M. SHELXTL V5.1 Software Reference Manual;Bruker AXS Inc.: Madison, 1997.
15	Maia J. D. C. ; Carvalho G. A. U. ; Mangueira C. P. ; ; Jr.; Santana S. R. ; Cabral L. A. F. ; Rocha G. B. J. , Chem. Theory Comput. 2012, 8 (9), 3072.
16	McNaught I. J. J. , Chem. Educ. 2011, 88 (4), 421.
17	Stewart J. J. P. J. , Mol. Model.
18	Stewart J. J. P. J. , Comput. Chem. 2011, 32 (7), 1456.
19	Grimme S. ; Antony J. ; Ehrlich S. ; Krieg H. J. , Chem. Phys. 2010, 132 (15), 15404.
20	Song J. S. ; Klein E. L. ; Neese F. ; Ye S. F. Inorg. Chem. 2014, 53 (14), 7500.
21	Atak K. ; Golnak R. ; Xiao J. ; Suljoti E. ; Pfluger M. ; Brandenburg T. ; Winter B. ; Azi E. ; F J. Phys. Chem. B 2014, 118 (33), 9938.
22	Neese F. ; Wennmohs F. ; Hansen A. ; BeckerU. Chem. Phys. 2009, 365 (1-3), 98.
23	Weigend F. ; Ahlrichs R. Phys. Chem. Chem. Phys. 2005, 7 (18), 3297.
24	Yang Y. J. Phys. Chem. A 2010, 114 (50), 13257.
25	Zou W. L. ; Nori-Shargh D. ; Boggs J. E. J. , Phys. Chem. A A2013, 117 (1), 207.
26	Lu T. ; Chen F.W. J. , Phys. Chem. A 2013, 117 (14), 3100.
27	Arunan E. ; Desiraju G. R. ; Klein R. A. ; Sadle J. Pure Appl. Chem. 2011, 83, 1619.
28	Hibbert F. ; Emsley H. Adv. Phys. Org. Chem. 1991, 26, 255.
29	Akhriff Y. ; Server-Carrio J. ; Garcia-Lozano J. ; Folgado J. V. ; Sancho S. ; Escriva E. ; Vitoria P. Crystal Growth Design 2006, 6 (5), 1124.
30	Silva C. E. ; Dos Santos H. F. ; Speziali N. L. ; Diniz R. ; deOliveira L. F. C. J. , Phys. Chem. A 2010, 114 (37), 10097.
31	Inkaya E. ; Günnaz S. ; Özdemir N. ; Dayan O. ; Dinçer M. ; Çetinkaya B. Spectrochim. Acta A 2013, 103, 255.
32	Schwager F. ; Marand E. ; Davis R. M. J. , Phys. Chem. 1996, 100 (50), 19268.
33	Desseyn H. O. ; Clou K. ; Keuleers R. ; Miao R. ; Van Doren V. E. ; Blaton N. Spectrochim. Acta A 2001, 57 (2), 231.
34	Hao M. H. J. , Chem. Theory Comput. 2006, 2 (3), 863.
35	Lane J. R. J. , Chem. Theory Comput. 2013, 9 (1), 316.
36	Lipkowski P. ; Grabowski S. J. ; Robinson T. L. ; Leszczynski J. J. , Phys. Chem. A 2004, 10 8 (49), 10865.
37	Grabowski S. J. ; Dubis A. T. ; Palusiak M. ; Leszczynski J. J. , Phys. Chem. B 2006, 110 (12), 5875.
38	Grabowski S. J. J. , Phys. Org. Chem. 2013, 26 (6), 452.
39	Rybarczyk-Pirek A. J. Struct. Chem. 2012, 23 (6), 1739.
40	Chou P. T. ; Ching Y.W. ; Hung F. T. J. , Phys. Chem. B 1997, 101 (44), 9119.
41	Latosinska J. N. ; Latosinska M. ; Seliger J. ; Zagar V. ; Maurin J. K. ; Kazimierczuk Z. J. , Phys. Chem. A 2012, 116 (5), 1445.
42	Latosińska J. N. ; Latosińska M. ; Maurin J. K. ; Orzeszko A. ; Kazimierczuk Z. J. , Phys. Chem. A 2014, 118 (11), 2089.
43	Rozas I. ; Alkorta I. ; Elguero J. J. , Am. Chem. Soc. 2000, 122 (45), 11154.
44	Espinosa E. ; Molins E. ; Lecomte C. Chem. Phys. Lett. 1998, 285 (3-4), 170.

[1]	Xingang Fei, Haiyan Tan, Bei Cheng, Bicheng Zhu, Liuyang Zhang. 2D/2D Black Phosphorus/g-C₃N₄ S-Scheme Heterojunction Photocatalysts for CO₂ Reduction Investigated using DFT Calculations [J]. Acta Phys. -Chim. Sin., 2021, 37(6): 2010027-0.
[2]	Yunfei Wang, Jianhua Liu, Mei Yu, Jinyan Zhong, Qisen Zhou, Junming Qiu, Xiaoliang Zhang. SnO₂ Surface Halogenation to Improve Photovoltaic Performance of Perovskite Solar Cells [J]. Acta Phys. -Chim. Sin., 2021, 37(3): 2006030-0.
[3]	Xuezhu Xiao, Xiaofang Cao, Dongbo Zhao, Chunying Rong, Shubin Liu. Quantification of Molecular Basicity for Amines: a Combined Conceptual Density Functional Theory and Information-Theoretic Approach Study [J]. Acta Physico-Chimica Sinica, 2020, 36(11): 1906034-0.
[4]	Zhichao Huang,Yazhong Dai,Xiaojie Wen,Dan Liu,Yuxuan Lin,Zhen Xu,Jian Pei,Kai Wu. Conformational Switching of Verdazyl Radicals on Au(111) [J]. Acta Physico-Chimica Sinica, 2020, 36(1): 1907043-0.
[5]	Dan WANG,Xunlei DING,Henglu LIAO,Jiayu DAI. Methane Activation on (Au/Ag)₁-Doped Vanadium Oxide Clusters [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1005-1013.
[6]	Qiang CHEN,Li-Xue JIANG,Hai-Fang LI,Jiao-Jiao CHEN,Yan-Xia ZHAO,Sheng-Gui HE. Thermal Activation of Methane by Diatomic Vanadium Boride Cations [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1014-1020.
[7]	Mengru HAN,Yanan ZHOU,Xuan ZHOU,Wei CHU. Tunable Reactivity of MNi₁₂ (M = Fe, Co, Cu, Zn) Nanoparticles Supported on Graphitic Carbon Nitride in Methanation [J]. Acta Physico-Chimica Sinica, 2019, 35(8): 850-857.
[8]	Yue ZHAO,Jiatong CUI,Jichuang HU,Jiabi MA. Reactivities of VO_1–4⁺ Toward n-C_mH_2m+2 (m = 3, 5, 7) as Functions of Oxygen Content and Carbon Chain Length [J]. Acta Phys. -Chim. Sin., 2019, 35(5): 531-538.
[9]	Martínez GONZÁLEZ Marco,Carlos CÁRDENAS,Juan I. RODRÍGUEZ,Shubin LIU,Farnaz HEIDAR-ZADEH,Ramón Alain MIRANDA-QUINTANA,Paul W. AYERS. Quantitative Electrophilicity Measures [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 662-674.
[10]	Paul W. AYERS,Mel LEVY. Levy Constrained Search in Fock Space: An Alternative Approach to Noninteger Electron Number [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 625-630.
[11]	Tian LU,Qinxue CHEN. Revealing Molecular Electronic Structure via Analysis of Valence Electron Density [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 503-513.
[12]	Farnaz HEIDAR-ZADEH,Paul W. AYERS. Generalized Hirshfeld Partitioning with Oriented and Promoted Proatoms [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 514-518.
[13]	Yueqi YIN,Mengxu JIANG,Chunguang LIU. DFT Study of POM-Supported Single Atom Catalyst (M₁/POM, M = Ni, Pd, Pt, Cu, Ag, Au, POM = [PW₁₂O₄₀]^3-) for Activation of Nitrogen Molecules [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 270-277.
[14]	Fanhua YIN,Kai TAN. Density Functional Theory Study on the Formation Mechanism of Isolated-Pentagon-Rule C₁₀₀(417)Cl₂₈ [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 256-262.
[15]	Robert C MORRISON. Fukui Functions for the Temporary Anion Resonance States of Be^-, Mg^-, and Ca^- [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 263-269.

Experimental and Theoretical Evidence for Supramolecular Self-Assembly and Hydrogen Bonding between Squaric Acid and 2, 6-Bis(2-benzimidazolyl)pyridine

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 0