A combined theoretical and cambridge structural database study of π-hole pnicogen bonding complexes between electron rich molecules and both nitro compounds and inorganic bromides (YO2Br, y = N, P, and As)

Journal of Physical Chemistry A

Volumn 118, Issue 15, 2014, Pages 2827-2834

  Bauzá, Antonio ^a   Ramis, Rafael ^a   Frontera, Antonio ^a  

^a UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC CHEMISTRY;

ATOMS IN MOLECULES; CAMBRIDGE STRUCTURAL DATABASES; CRYSTAL PACKINGS; HOLE INTERACTIONS; HYDROGEN FLUORIDE; QUANTUM CALCULATION; SOLID-STATE ARCHITECTURES; X-RAY STRUCTURE;

MOLECULES;

AMMONIA; BROMIDE; HYDROFLUORIC ACID; LEWIS BASE; METHANE; NITRITE; NITROALKANE; NITROMETHANE; WATER;

ANALOGS AND DERIVATIVES; CHEMISTRY; HYDROGEN BOND; QUANTUM THEORY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

AMMONIA; BROMIDES; CRYSTALLOGRAPHY, X-RAY; HYDROFLUORIC ACID; HYDROGEN BONDING; LEWIS BASES; METHANE; NITRITES; NITROPARAFFINS; QUANTUM THEORY; THERMODYNAMICS; WATER;

EID: 84898928145     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp502301n     Document Type: Article

References (63)

1. Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Supramolecular Chemistry in Water Angew. Chem., Int. Ed. 2007, 46, 2366-2393
2. Dsouza, R. N.; Pischel, U.; Nau, W. M. Fluorescent Dyes and their Supramolecular Host-Guest Complexes with Macrocycles in Aqueous Solution Chem. Rev. 2011, 111, 7941-7980
3. Zürcher, M.; Diederich, F. Structure-Based Drug Design: Exploring the Proper Filling of Apolar Pockets at Enzyme Active Sites J. Org. Chem. 2008, 73, 4345-4361
4. Smith, D. K. A Supramolecular Approach to Medicinal Chemistry: Medicine Beyond Molecule J. Chem. Educ. 2005, 82, 393-400
5. Uhlenheuer, D. A.; Petkau, K.; Brunsveld, L. Combining Supramolecular Chemistry with Biology Chem. Soc. Rev. 2010, 39, 2817-2826
6. Ma, J. C.; Dougherty, D. A. The Cation-π Interaction Chem. Rev. 1997, 97, 1303-1324
7. Zacharias, N.; Dougherty, D. A. Cation-π Interactions in Ligand Recognition and Analysis Trends Pharmacol. Sci. 2002, 23, 281-287
8. Frontera, A.; Gamez, P.; Mascal, M.; Mooibroek, T. J.; Reedijk, J. Putting Anion-π Interactions into Perspective Angew. Chem. Int. Ed. 2011, 50, 9564-9583
9. Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Supramolecular Chemistry of Anions Chem. Soc. Rev. 2008, 37, 68-83
10. Hay, B. P.; Bryantsev, V. S. Anion Arene Adducts: C-H Hydrogen Bonding, Anion-π Interaction, and Carbon Motifs Bonding Chem. Commun. 2008, 2417-2428
11. Frontera, A. Encapsulation of Anions: Macrocyclic Receptors Based on Metal Coordination and Anion-π Interactions Coord. Chem. Rev. 2013, 257, 1716-1727
12. + Rings New J. Chem. 2013, 37, 2636-2641
13. Bauzá, A.; Quiñonero, D.; Deyà, P. M.; Frontera, A. Theoretical ab initio Study of Anion-π Interactions in Inorganic Rings Chem. Phys. Lett. 2012, 530, 145-150
14. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with Aromatic Rings in Chemical and Biological Recognition Angew. Chem., Int. Ed. Engl. 2003, 42, 1210-1250
15. Salonen, L. M.; Ellermann, M.; Diederich, F. Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures Angew. Chem., Int. Ed. 2011, 50, 4808-4842
16. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond; Oxford University Press: Oxford, 1999.
17. Steiner, T. The Hydrogen Bond in the Solid State Angew. Chem., Int. Ed. 2002, 41, 48-76
18. Castellano, R. K. Progress toward Understanding the Nature and Function of C-H⋯O Interactions Curr. Org. Chem. 2004, 8, 845-865
19. Legon, A. C. The Halogen Bond: an Interim Perspective Phys. Chem. Chem. Phys. 2010, 12, 7736-7747
20. Scholfield, M. R.; Van der Zanden, C. M.; Carter, M.; Ho, P. S. Halogen Bonding (X-Bonding): a Biological Perspective Protein Sci. 2013, 22, 139-152
21. Erdelyi, M. Halogen Bonding in Solution Chem. Soc. Rev. 2012, 41, 3547-3557
22. Parisini, E.; Metrangolo, P.; Pilati, T.; Resnati, G.; Terraneo, G. Halogen Bonding in Halocarbon-Protein Complexes: a Structural Survey Chem. Soc. Rev. 2010, 40, 2267-2278
23. Schneider, H.-J. Binding Mechanisms in Supramolecular Complexes Angew. Chem., Int. Ed. Engl. 2009, 48, 3924-3977
24. Politzer, P.; Murray, J. S.; Clark, T. Halogen Bonding and Other σ-Hole Interactions: a Perspective Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
25. Murray, J. S.; Lane, P.; Clark, T.; Riley, K. E.; Politzer, P. σ-Holes, π-Holes and Electrostatically Driven Interactions J. Mol. Model. 2012, 18, 541-548
26. Clark, T.; Henneman, M.; Murray, J. S.; Politzer, P. Halogen Bonding: the Sigma Hole J. Mol. Model. 2007, 13, 291-296
27. Murray, J. S.; Riley, K. E.; Politzer, P.; Clark, T. Directional Weak Intermolecular Interactions: Sigma-Hole Bonding Aust. J. Chem. 2010, 63, 1598-1607
28. Bauzá, A.; Mooibroek, T. J.; Frontera, A. Tetrel Bonding: A Rediscovered Supramolecular Force? Angew. Chem., Int. Ed. 2013, 52, 12317-12321
29. N2 Reaction Phys. Chem. Chem. Phys. 2014, 16, 1824-1834
30. 2NX) with HCN and HNC Struct. Chem. 2013, 24, 651-659
31. Esrafili, M. D.; Mohammadian-Sabet, F.; Solimannejad, M. A Theoretical Evidence for Mutual Influencie Between S⋯N(C) and Hydrogen/Lithium/ Halogen Bond: Competition and Interplay Between π-Hole and σ-Hole Interactions Struct Chem. 2014, 10.1007/s11224-014-0392-8
32. Solimannejad, M.; Ramezani, V.; Trujillo, C.; Alkorta, I.; Sánchez-Sanz, G.; Elguero, J. Competition and Interplay between σ-Hole and π-Hole Interactions: a Computational Study of 1:1 and 1:2 Complexes of Nitryl Halides (O2NX) with Ammonia J. Phys. Chem. A 2012, 116, 5199-5206
33. 3, and BH2: P⋯P Pnicogen Bonding at σ-Holes and π-Holes J. Phys. Chem. A 2013, 117, 11592-11604
34. 2 on Aqueous Bromide Solutions J. Phys. Chem. A 1998, 102, 10689-10696
35. X Species Geophys. Res. Lett. 1986, 13, 933-936
36. Molina, M. J.; Rowland, F. S. Stratospheric Sink for Chlorofluoromethanes: Chlorine Atom-Catalysed Destruction of Ozone Nature 1974, 249, 810-812
37. Wayne, R. P. Chemistry of Atmospheres; Oxford University Press: Oxford, U.K., 1991.
38. von Glasow, R. Atmospheric Chemistry in Volcanic Plumes Proc. Nat. Acad. Sci. 2010, 107, 6594-6599
39. Sánchez-Sanz, G.; Trujillo, C.; Solimannejad, M.; Alkorta, I.; Elguero, J. Orthogonal Interactions between Nitryl Derivatives and Electron Donors: Pnictogen Bonds Phys. Chem. Chem. Phys. 2013, 15, 14310-14318
40. 2 J. Phys. Chem. A 2013, 117, 6893-6903
41. 2Br Matrix-IR-Untersuchungen und ab initio SCF-Rechnungen ZAAC 1989, 579, 66-74
42. Allen, F. H. The Cambridge Structural Database: a Quarter of a Million Crystal Structures and Rising Acta Crystallogr. 2002, B58, 380-388
43. Bader, R. F. W. A Quantum Theory of Molecular Structure and its Applications Chem. Rev. 1991, 91, 893-928
44. Bader, R. F. W. Atoms in Molecules, A Quantum Theory; Oxford University Press: Oxford, UK, 1990.
45. Popelier, P. L. A. Atoms In Molecules. An Introduction; Prentice Hall: Harlow, England, 2000.
46. Ahlrichs, R.; Bär, M.; Hacer, M.; Horn, H.; Kömel, C. Electronic Structure Calculation on Workstation Computers: The Program System Turbomole Chem. Phys. Lett. 1989, 162, 165-169
47. Boys, S. B.; Bernardi, F. The Calculation of Small Molecular Interactions by the Differences of Separate Total Energies. Some Procedures with Reduced Errors Mol. Phys. 1970, 19, 553-566
48. Todd, A.; Keith, T. K. AIMall, version 13.05.06; Gristmill Software: Overland Park, KS, 2013.
49. 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 B.01; Gaussian, Inc.: Wallingford, CT, 2009.
50. Bauzá, A.; Quiñonero, D.; Frontera, A.; Deyà, P. M. Substituent Effects in Halogen Bonding Complexes between Aromatic Donors and Acceptors: A Comprehensive ab initio Study Phys. Chem. Chem. Phys. 2011, 13, 20371-20379
51. Lucas, X.; Frontera, A.; Quiñonero, D.; Deyà, P. M. Substituent Effects in Ion-pi Interactions: Fine-Tuning via the Ethynyl Group J. Phys. Chem. A 2010, 114, 1926-1930
52. Escudero, D.; Estarellas, C.; Frontera, A.; Quiñonero, D.; Deyà, P. M. Theoretical and Crystallographic Study of Edge-To-Face Aromatic Interactions between Pyridine Moieties and Benzene Chem. Phys. Lett. 2009, 468, 280-285
53. Nangia, A.; Biradha, K.; Desiraju, G. R. Correlation of biological activity in β-lactam antibiotics with Woodward and Cohen structural parameters-a Cambridge database study J. Chem. Soc., Perkin Trans. 2 1996, 943-953
54. Cresswell, A. J.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Russell, A. J.; Thomson, J. E.; Tyte, M. J. β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides Org. Lett. 2010, 12, 2936-2939
55. Clapham, K. M.; Batsanov, A. S.; Bryce, M. R.; Tarbit, B. Trifluoromethyl-Substituted Pyrydyl- and Pyrazolylboronic Acids and Esters: Synthesis and Suzuki-Miyaura Cross-Coupling Reactions Org. Biomol. Chem. 2009, 7, 2155-2161
56. Fun, H.-K.; Goh, J. H.; Chandrakantha, B.; Isloor, A. M.; Shetty, P. 2-Chloro-4-nitro-1H-imidazole Acta Crystallogr. 2010, E66, o1828-o1829
57. Ravikumar, K.; Sridhar, B.; Mahesh, M.; Reddy, V. V. N. 1-[5-(4-Fluorophenyl)-1,2-oxazol-3-ylmethyl]-2-nitroiminoimidazolidine Acta Crystallogr. 2006, E62, o3850-o3851
58. Manivannan, S.; Dhanuskodi, S.; Kirschbaum, K.; Tiwari, S. K. Design of an Efficient Solution Grown Semiorganic NLO Crystal for Short Wavelenght Generation: 2-Amino-5-nitropyridinium Tetrafluoroborate Cryst. Growth Des. 2005, 5, 1463-1468
59. Rathore, R. S.; Narasimhamurthy, T.; Vijay, T.; Yathirajan, H. S.; Nagaraja, P. 5-Chlorocarbonyl-10,11-dihydro-5H-dibenz[ b, f ] azepine Acta Crystallogr. 2006, C62, o36-o38
60. Zaleski, J.; Daszkiewicz, Z.; Kyziol, J. 1-Methyl-4-(N -methylnitramino) Pyridinium Bromide Acta Crystallogr. 1999, C55, 691-693
61. 4]2 {L=2,5,8-Trithia[9](2,9)-1,10-phenanthrolinophane} J. Chem. Soc., Dalton Trans. 1999, 1085-1902
62. 2 Eur. J. Inorg. Chem. 2005, 479-485
63. Schottel, B. L.; Chifotides, H. T.; Shatruk, M.; Chouai, A.; Perez, L. M.; Bacsa, J.; Dunbar, K. R. Anion-π Interactions as Controlling Elements in Self-Assembly Reactions of Ag(I) Complexes with π-Acidic Aromatic Rings J. Am. Chem. Soc. 2006, 128, 5895-5912