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.

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

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