Recognition of a novel type X=N-Hal...Hal (X = C, S, P; Hal = F, Cl, Br, I) halogen bonding

Journal of Physical Chemistry A

Volumn 117, Issue 13, 2013, Pages 2827-2834

  Gushchin, Pavel V ^a   Kuznetsov, Maxim L ^b   Haukka, Matti ^c   Kukushkin, Vadim Yu ^a,d  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^d INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

CAMBRIDGE STRUCTURAL DATABASES; CL ATOMS; HALOGEN BONDING; IMINO GROUPS; MOLECULAR SPECIES; STRUCTURAL DATA; THEORETICAL CALCULATIONS; X-RAY STUDIES;

BONDING; CHEMICAL BONDS; DATA HANDLING; DENSITY FUNCTIONAL THEORY; FLUORINE; IODINE; PLATINUM; PLATINUM COMPOUNDS;

CHLORINE COMPOUNDS;

EID: 84875845930     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3112149     Document Type: Article

References (86)

1. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Halogen Bonding in Supramolecular Chemistry Angew. Chem., Int. Ed. 2008, 47 (33) 6114-6127
2. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Halogen Bonding Based Recognition Processes: A World Parallel to Hydrogen Bonding Acc. Chem. Res. 2005, 38 (5) 386-395
3. Metrangolo, P.; Resnati, G. Halogen Bonding: A Paradigm in Supramolecular Chemistry Chem.-Eur. J. 2001, 7 (12) 2511-2519
4. Metrangolo, P.; Resnati, G. Halogen Bonding: Where We Are and Where We Are Going Cryst. Growth Des. 2012, 12 (12) 5835-5838
5. Bruce, W. D.; Metrangolo, P.; Meyer, F.; Prasang, C.; Resnati, G.; Terraneo, G.; Whitwood, A. C. Mesogenic, Trimeric, Halogen-Bonded Complexes from Alkoxystilbazoles and 1,4-Diiodotetrafluorobenzene New J. Chem. 2008, 32, 477-482
6. Metrangolo, P.; Resnati, G. Halogen Versus Hydrogen Science 2008, 321, 918-919
7. Mele, A.; Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. A Halogen-Bonding-Based Heteroditopic Receptor for Alkali Metal Halides J. Am. Chem. Soc. 2005, 127 (43) 14972-14973
8. Imakubo, T.; Kibune, M.; Yoshino, H.; Shirahata, T.; Yoza, K. Hexagonal Supramolecular Organic Conductors Based on Diiodo(pyrazino)tetraselenafulvalene: High Yield Recovery of the Neutral p-Donor by a Simple Chemical Reaction J. Mater. Chem. 2006, 16, 4110-4116
9. Rissanen, K. Halogen Bonded Supramolecular Complexes and Networks CrystEngComm 2008, 10, 1107-1113
10. Castellote, I.; Morón, M.; Burgos, C.; Alvarez-Builla, J.; Martin, A.; Gómez-Sal, P.; Vaquero, J. J. Reaction of Imines with N-iodosuccinimide (NIS): Unexpected Formation of Stable 1:1 Complexes Chem. Commun. 2007, 1281-1283
11. El-Sheshtawy, H. S.; Bassil, B. S.; Assaf, K. I.; Kortz, U.; Nau, W. M. Halogen Bonding inside a Molecular Container J. Am. Chem. Soc. 2012, 134 (48) 19935-19941
12. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Mutual Induced Coordination in Halogen-Bonded Anionic Assemblies with (6,3) Cation-Templated Topologies Chem. Commun. 2008, 1635-1637
13. Gattuso, G.; Pappalardo, A.; Parisi, M. F.; Pisagatti, I.; Crea, F.; Liantonio, R.; Metrangolo, P.; Navarrini, W.; Resnati, G.; Pilati, T.; Pappalardo, S. Dipyridinocalixcrown/diiodoperfluorocarbon Binary Host Systems for CsI: Structural Studies and Fluorous Phase Extraction of Caesium Tetrahedron 2007, 63, 4951-4958
14. Gattuso, G.; Liantonio, R.; Metrangolo, P.; Meyer, F.; Pappalardo, A.; Parisi, M. F.; Pilati, T.; Pisagatti, I.; Resnati, G. Hybrid Calixarene/Inorganic Salt/Diiodoperfluorocarbon Supramolecular Assemblies Supramol. Chem. 2006, 18 (3) 235-243
15. Logothetis, T. A.; Meyer, F.; Metrangolo, P.; Pilati, T.; Resnati, G. Crystal Engineering of Brominated Tectons: N-methyl-3,5-dibromopyridinium Iodide Gives Particularly Short C-Br...I Halogen Bonding New J. Chem. 2004, 28, 760-763
16. Liantonio, R.; Metrangolo, P.; Pilati, T.; Resnati, G. Fluorous Interpenetrated Layers in a Three-Component Crystal Matrix Cryst. Growth Des. 2003, 3 (3) 355-361
17. Metrangolo, P.; Pilati, T.; Terraneo, G.; Biella, S.; Resnati, G. Anion Coordination and Anion-Templated Assembly under Halogen Bonding Control CrystEngComm 2009, 11, 1187-1196
18. 3- under Modular Cation Templation Cryst. Growth Des. 2012, 12 (11) 5757-5762
19. Desiraju, G. R.; Parthasarathy, R. The Nature of Halogen...Halogen Interactions: Are Short Halogen Contacts Due to Specific Attractive Forces or Due to Close Packing of Nonspherical Atoms? J. Am. Chem. Soc. 1989, 111 (23) 8725-8726
20. Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Raeb, A. D.; Desiraju, G. R. The Nature of Halogen...Halogen Interactions and the Crystal Structure of 1,3,5,7-Tetraiodoadamantane J. Chem. Soc. Perkin Trans. 2 1994, 2353-2360
21. Rajput, L.; Mukherjee, G.; Biradha, K. Influence of Solvents in Assembling Tris(4-halophenyl)benzene-1,3,5-tricarboxamides: Interplay of N-H...O and Halogen...Halogen Interactions Cryst. Growth Des. 2012, 12 (11) 5773-5782
22. Chung, K.-H.; Kim, H.; Jang, W. J.; Yoon, J. K.; Kahng, S.-J.; Lee, J.; Han, S. Molecular Multistate Systems Formed in Two-Dimensional Porous Networks on Ag(111) J. Phys. Chem. C 2013, 117, 302-306
23. Natale, D.; Marequerivas, J. C. The Combination of Transition Metal Ions and Hydrogen-Bonding Interactions Chem. Commun. 2008, 425-437
24. Feller, R. K.; Chetham, A. K. Structural and Chemical Complexity in Multicomponent Inorganic-Organic Framework Materials CrystEngComm 2009, 11, 980-985
25. Corradi, E.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G. Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes Angew. Chem., Int. Ed. 2000, 39 (10) 1782-1786
26. Desiraju, G. R. Crystal Engineering: A Holistic View Angew. Chem., Int. Ed. 2007, 46 (44) 8342-8356
27. Holliday, B. J.; Mirkin, C. A. Strategies for the Construction of Supramolecular Compounds through Coordination Chemistry Angew. Chem., Int. Ed. 2001, 40 (11) 2022-2043
28. Cincic, D.; Friscic, T.; Jones, W. Structural Equivalence of Br and I Halogen Bonds: A Route to Isostructural Materials with Controllable Properties Chem. Mater. 2008, 20 (21) 6623-6626
29. II Center Giving an Eight-Membered Chelated Platinaguanidine Inorg. Chem. 2009, 48 (6) 2583-2592
30. Gushchin, P. V.; Tyan, M. R.; Bokach, N. A.; Revenco, M. D.; Haukka, M.; Wang, M.-J.; Lai, C.-H.; Chou, P.-T.; Kukushkin, V. Y. Novel Tailoring Reaction for Two Adjacent Coordinated Nitriles Giving Platinum 1,3,5-Triazapentadiene Complexes Inorg. Chem. 2008, 47 (24) 11487-11500
31. Bokach, N. A.; Kuznetsova, T. V.; Simanova, S. A.; Haukka, M.; Pombeiro, A. J. L.; Kukushkin, V. Y. Nitrile-Amidine Coupling at Pt(IV) and Pt(II) Centers. An Easy Entry to Imidoylamidine Complexes Inorg. Chem. 2005, 44 (14) 5152-5160
32. Sarova, G. H.; Bokach, N. A.; Fedorov, A. A.; Berberan-Santos, M. N.; Kukushkin, V. Y.; Haukka, M.; Silva, J. J. R. F. d.; Pombeiro, A. J. L. A New Family of Luminescent Compounds: Platinum(II) Imidoylamidinates Exhibiting pH-Dependent Room Temperature Luminescence Dalton Trans. 2006, 3798-3805
33. Tskhovrebov, A. G.; Bokach, N. A.; Haukka, M.; Kukushkin, V. Y. Different Routes for Amination of Platinum(II)-Bound Cyanoguanidine Inorg. Chem. 2009, 48 (18) 8678-8688
34. Bokach, N. A.; Pakhomova, T. B.; Kukushkin, V. Y.; Haukka, M.; Pombeiro, A. J. L. Hydrolytic Metal-Mediated Coupling of Dialkylcyanamides at a Pt(IV) Center Giving a New Family of Diimino Ligands Inorg. Chem. 2003, 42 (23) 7560-7568
35. Makarycheva-Mikhailova, A. V.; Bokach, N. A.; Kukushkin, V. Y.; Kelly, P. F.; Gilby, L. M.; Kuznetsov, M. L.; Holmes, K. E.; Haukka, M.; Parr, J.; Stonehouse, J. M.; Elsegood, M. R. J.; Pombeiro, A. J. L. Platinum(IV)-Mediated Nitrile-Sulfimide Coupling: A Route to Heterodiazadienes Inorg. Chem. 2003, 42 (2) 301-311
36. Cini, R.; Caputo, P. A.; Intini, F. P.; Natile, G. Mechanistic and Stereochemical Investigation of Imino Ethers Formed by Alcoholysis of Coordinated Nitriles: X-ray Crystal Structures of cis- and trans-Bis(1-imino-1- methoxyethane)dichloroplatinum(II) Inorg. Chem. 1995, 34 (5) 1130-1137
37. 2] Inorg. Chim. Acta 2002, 334, 437-447
38. 2 Inorg. Chem. Commun. 2001, 4, 275-280
39. Cini, R.; Fanizzi, F. P.; Intini, F. P.; Natile, G.; Pacifico, C. Isomerism of Amides Coordinated to Platinum. X-ray Crystal Structure of Dichloro-Bisacetamide-Platinum(II) Inorg. Chim. Acta 1996, 251 (1-2) 111-118
40. Gonzalez, A. M.; Cini, R.; Intini, F. P.; Pacifico, C.; Natile, G. X-ray Structures of the First Platinum Complexes with Z Configuration Iminoether Ligands: trans -Dichlorobis(1-imino-1-methoxy-2,2′-dimethylpropane) platinum(II) and trans -Tetrachlorobis(1-imino-1-methoxy-2,2′- dimethylpropane)platinum(IV) Inorg. Chem. 2002, 41 (3) 470-478
41. Tanatani, A.; Yamaguchi, K.; Azumaya, I.; Fukutomi, R.; Shudo, K.; Kagechika, H. N -Methylated Diphenylguanidines: Conformations, Propeller-Type Molecular Chirality, and Construction of Water-Soluble Oligomers with Multilayered Aromatic Structures J. Am. Chem. Soc. 1998, 120 (26) 6433-6442
42. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2008.
43. Beyerle-Pfnür, R.; Lippert, B.; Schöllhorn, H.; Matischok, P.; Thewalt, U. Chlorimine Formation and Deamination of the Model Nucleobase 1-Methylcytosine J. Heterocycl. Chem. 1986, 23 (2) 505-508
44. Privett, A. J.; Craig, S. L.; Jeter, D. Y.; Cordes, A. W.; Oakley, R. T.; Reed, R. W. Structure of N -(N -chlorobenzimidoyl)benzamidinium Decachlorodiselenate(IV) Acetonitrile Solvate Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1987, 43, 2023-2025
45. Martinu, T.; Dailey, W. P. Reactivity of 1-Chloro-3-phenyldiazirines J. Org. Chem. 2006, 71 (13) 5012-5015
46. 2 Z. Anorg. Allg. Chem. 1995, 621 (9) 1489-1495
47. 3(bipy)VNCl Z. Anorg. Allg. Chem. 1979, 452 (1) 123-140
48. n Complexes Chem. Phys. Lett. 2006, 427, 51-55
49. Wang, Y.-H.; Lu, Y.-X.; Zou, J.-W.; Yu, Q.-S. Theoretical Investigation on Charge-Assisted Halogen Bonding Interactions in the Complexes of Bromocarbons with Some Anions Int. J. Quantum Chem. 2008, 108 (1) 90-99
50. Lu, Y.-X.; Zou, J.-W.; Wang, Y.-H.; Jiang, Y.-J.; Yu, Q.-S. Ab Initio Investigation of the Complexes between Bromobenzene and Several Electron Donors: Some Insights into the Magnitude and Nature of Halogen Bonding Interactions J. Phys. Chem. A 2007, 111 (42) 10781-10788
51. Forni, A. Experimental and Theoretical Study of the Br...N Halogen Bond in Complexes of 1,4-Dibromotetrafluorobenzene with Dipyridyl Derivatives J. Phys. Chem. A 2009, 113 (14) 3403-3412
52. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen J. Am. Chem. Soc. 1996, 118 (13) 3108-3116
53. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An Overview of Halogen Bonding J. Mol. Model. 2007, 13 (2) 305-311
54. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen Bonding: the σ-Hole J. Mol. Model. 2007, 13 (2) 291-296
55. Awwadi, F. F.; Willet, R. D.; Peterson, K. A.; Twamley, B. The Nature of Halogen...Halogen Synthons: Crystallographic and Theoretical Studies Chem.-Eur. J. 2006, 12 (35) 8952-8960
56. -). The Connection between Hypervalent, Electron-Rich Three-Center, Donor-acceptor and Strong Hydrogen Bonding J. Chem. Soc., Dalton Trans. 1997, 19, 3605-3613
57. Hiraoka, K.; Mizuno, T.; Iino, T.; Eguchi, D.; Yamabe, S. Characteristic Changes of Bond Energies for Gas-Phase Cluster Ions of Halide Ions with Methane and Chloromethanes J. Phys. Chem. A 2001, 105 (20) 4887-4893
58. - Interaction of Fluoromethanes and Chloromethanes with Fluoride, Chloride, and Hydroxide Anions J. Phys. Chem. A 2002, 106 (29) 6832-6838
59. 3: Towards Understanding the Nature of Halogen Bonding and the Electron-Accepting Propensities of Covalently Bonded Halogen Atoms Chem.-Eur. J. 2005, 11 (2) 740-751
60. Deadman, J. J.; Jarman, M.; McCague, R.; McKenna, R.; Neidle, S. A Benzoquinone Di-imine from the Oxidation of Pentafluoroaniline by Hypochlorite. X-Ray Crystal Structure and Possible Formation via Pentafluorophenylnitrene J. Chem. Soc., Perkin Trans. 2 1989, 8) 971-975
61. Praly, J.-P.; Senni, D.; Faure, R.; Descotes, G. Synthesis and Structure of Bromo Glycosyl Imines Readily Obtained from Protected Glycosyl Azides Tetrahedron 1995, 51 (6) 1697-1708
62. Grebe, J.; Geiseler, G.; Harms, K.; Neumuller, B.; Dehnicke, K. Domino Effect in the Buildup of N-I-N-I Chains of the N-Iodine(triphenylphosphane)imine Angew. Chem., Int. Ed. 1999, 38 (1-2) 222-225
63. 2I]Cl-ein Donor-Akzeptorkomplex von N-Iod(triethylphosphan)imin an Iodmonochlorid Z. Anorg. Allg. Chem. 2003, 629 (7-8) 1110-1112
64. Grebe, J.; Geiseler, G.; Harms, K.; Neumuller, B.; Dehnicke, K. Domino Effect in the Buildup of N-I-N-I Chains of the N-Iodine(triphenylphosphane)imine Angew. Chem., Int. Ed. 1999, 38 (1-2) 222-225
65. 2 Z. Anorg. Allg. Chem. 1994, 620 (2) 329-333
66. Gowda, B. T.; Tokarcik, M.; Kozisek, J.; Fuess, H. Sodium N -bromo-2,4-dichlorobenzenesulfonamidate Sesquihydrate Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63, m2115-m2116
67. Gowda, B. T.; Kozisek, J.; Tokarcik, M.; Fuess, H. Sodium N -bromo-4-chloro-2-methylbenzenesulfonamidate Sesquihydrate Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63, m1957
68. 2 Inorg. Chem. 1995, 34 (12) 3210-3214
69. Protasiewicz, J. D. (Tosyliminoiodo)benzene at 298K Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1996, 52 (6) 1570-1572
70. Dehnicke, K.; Hiller, W. Private Communication, 1992
71. 5(NCl)]-Synthesis and Crystal-Structure Z. Naturforsch., B: Chem. Sci. 1992, 47 (7) 1054-1056
72. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Academic Press: New York, 1997; pp 307-326.
73. Methods in Enzymology, Macromolecular Crystallography, Part A; Carter, C. W.; Sweet, J., Eds.; Academic Press: New York, 1997; Vol. 276, pp 307-326.
74. Altomare, A.; Burla, M. C.; Camalli, M. C.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. SIR97: A New Tool for Crystal Structure Determination and Refinement J. Appl. Crystallogr. 1999, 32, 115-119
75. Farrugia, L. J. WinGX Suite for Small-Molecule Single-Crystal Crystallography J. Appl. Crystallogr. 1999, 32, 837-838
76. Blessing, R. H. An Empirical Correction for Absorption Anisotropy Acta Crystallogr. 1995, A51, 33-38
77. Sheldrick, G. M. A Short History of SHELX Acta Crystallogr. 2008, A64, 112-122
78. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120 (1-3) 215-241
79. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, Revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
80. Gushchin, P. V.; Starova, G. L.; Haukka, M.; Kuznetsov, M. L.; Eremenko, I. L.; Kukushkin, V. Y. Chloride-Chloroform Clusters Exhibiting Weak Hydrogen and Halogen Bondings Are Fully Characterized in the Solid State by X-ray Diffraction Cryst. Growth Des. 2010, 10 (11) 4839-4846
81. 2 (Hal = Cl, Br, I) Hydrogen Bonding Dalton Trans. 2012, 41 (23) 6922-6931
82. Burns, L. A.; Vázquez-Mayagoitia, á.; Sumpter, B. G.; Sherrill, C. D. Density-Functional Approaches to Noncovalent Interactions: A Comparison of Dispersion Corrections (DFT-D), Exchange-Hole Dipole Moment (XDM) Theory, And Specialized Functionals J. Chem. Phys. 2011, 134 (8) 084107-1-25
83. Sumimoto, M.; Kawashima, Y.; Yokogawa, D.; Hori, K.; Fujimoto, H. Influences of dispersion and long-range corrections on molecular structures of three types of lithium phthalocyanine dimer Int. J. Quantum Chem. 2013, 113 (3) 272-276
84. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
85. Keith, T. A. AIMAll, Version 13.01.27; TK Gristmill Software: Overland Park KS, 2013, (aim.tkgristmill.com).
86. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88 (6) 899-926