Single electron pnicogen bonded complexes

Journal of Physical Chemistry A

Volumn 118, Issue 5, 2014, Pages 947-953

  Alkorta, Ibon ^a   Elguero, Jose ^a   Solimannejad, Mohammad ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b ARAK UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

BOND INTERACTIONS; INTERACTION ENERGIES; METHYL RADICAL; PNICOGENS; SINGLE ELECTRON; THEORETICAL STUDY; TRANSITION STATE; UNPAIRED ELECTRONS;

PHYSICAL CHEMISTRY; PHYSICS;

PHOSPHORUS COMPOUNDS;

EID: 84893871387     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp412144r     Document Type: Article

References (76)

1. 4 + X (X = Cl, Br): Application of G1 Theory J. Phys. Chem. 1991, 95, 9832-9836
2. 4 in Solid Ar J. Am. Chem. Soc. 1995, 117, 11997-11998
3. Alkorta, I.; Rozas, I.; Elguero, J. Radicals as Hydrogen Bond Acceptors Bunsen-Ges. Phys. Chem., Ber. 1998, 102, 429-435
4. Tachikawa, H. A Direct Ab Initio Dynamics Study on the Finite Temperature Effects on the Hyperfine Coupling Constant of a Weakly Bonded Complex J. Phys. Chem. A 1998, 102, 7065-7069
5. Igarashi, M.; Ishibashi, T.; Tachikawa, H. A Direct Ab Initio Molecular Dynamics Study of the Finite Temperature Effects on the Hyperfine Coupling Constant of Methyl Radical-Water Complexes J. Mol. Struct.: THEOCHEM 2002, 594, 61-69
6. Alkorta, I.; Elguero, J. Hydrogen Bond Acceptor Properties of Two Radicals: Nitric Oxide Molecule and Hydrogen Atom ARKIVOC 2003, xiv, 31-36
7. 3C···HCCH: An Ab Initio Study Chem. Phys. Lett. 2003, 375, 91-95
8. 3 Radicals: Hydrogen and Covalent Bonding Chem. Phys. Lett. 2005, 406, 351-354
9. 2 Radicals (A = B, Al, and Ga): A Theoretical Investigation J. Phys. Chem. A 2006, 110, 10817-10821
10. 2O Complex J. Phys. Chem. A 2008, 112, 5258-5263
11. Johnson, E.; Dilabio, G. Radicals as Hydrogen Bond Donors and Acceptors Interdiscip. Sci.: Comput. Life Sci. 2009, 1, 133-140
12. Li, Q.; Zhu, H.; An, X.; Gong, B.; Cheng, J. Nonadditivity of Methyl Group in Single-Electron Hydrogen Bond of Methyl Radical-Water Complex Int. J. Quantum Chem. 2009, 109, 605-611
13. 3; Y=CN, NC) J. Mol. Model. 2013, 19, 5031-5035
14. 3C Radicals as the Electron Donor: An Ab Initio Study Struct. Chem. 2012, 23, 411-416
15. Raghavendra, B.; Arunan, E. Unpaired and Σ Bond Electrons as H, Cl, and Li Bond Acceptors: An Anomalous One-Electron Blue-Shifting Chlorine Bond J. Phys. Chem. A 2007, 111, 9699-9706
16. 3) Sci. China: Chem. 2010, 53, 216-225
17. 3; X=Cl, Br) Mol. Phys. 2013, 10.1080/00268976.2013.864426
18. 3C···Li-Y (Y=H, F, OH, CN, NC, and CCH) Complexes J. Chem. Phys. 2006, 125, 084317
19. Sundberg, M. R.; Uggla, R.; Viñas, C.; Teixidor, F.; Paavola, S.; Kivekäs, R. Nature of Intramolecular Interactions in Hypercoordinate C-Substituted 1,2-Dicarba-Closo-Dodecaboranes with Short P·· ·P Distances Inorg. Chem. Commun. 2007, 10, 713-716
20. Tschirschwitz, S.; Lonnecke, P.; Hey-Hawkins, E. Aminoalkylferrocenyldichlorophosphanes: Facile Synthesis of Versatile Chiral Starting Materials Dalton Trans. 2007, 1377-1382
21. Bauer, S.; Tschirschwitz, S.; Lönnecke, P.; Frank, R.; Kirchner, B.; Clarke, M. L.; Hey-Hawkins, E. Enantiomerically Pure Bis(phosphanyl) carbaborane(12) Compounds Eur. J. Inorg. Chem. 2009, 2776-2788
22. Zahn, S.; Frank, R.; Hey-Hawkins, E.; Kirchner, B. Pnicogen Bonds: a New Molecular Linker? Chem.-Eur. J. 2011, 17, 6034-6038
23. Solimannejad, M.; Gharabaghi, M.; Scheiner, S. SH··· N and SH···P Blue-Shifting H-Bonds and N·· ·P Interactions in Complexes Pairing HSN with Amines and Phosphines J. Chem. Phys. 2011, 134, 024312
24. Scheiner, S. Effects of Multiple Substitution upon the P···N Noncovalent Interaction Chem. Phys. 2011, 387, 79-84
25. Scheiner, S. Effects of Substituents upon the P···N Noncovalent Interaction: The Limits of Its Strength J. Phys. Chem. A 2011, 115, 11202-11209
26. Scheiner, S. Can Two Trivalent N Atoms Engage in a Direct N···N Noncovalent Interaction? Chem. Phys. Lett. 2011, 514, 32-35
27. Scheiner, S. On the Properties of X···N Noncovalent Interactions for First-, Second-, and Third-Row X Atoms J. Chem. Phys. 2011, 134, 164313
28. Scheiner, S. Weak H-Bonds. Comparisons of CHO to NHO in Proteins and PHN to Direct PN Interactions Phys. Chem. Chem. Phys. 2011, 13, 13860-13872
29. Scheiner, S. A New Noncovalent Force: Comparison of P·· ·N Interaction with Hydrogen and Halogen Bonds J. Chem. Phys. 2011, 134, 094315
30. Scheiner, S.; Adhikari, U. Abilities of Different Electron Donors (D) to Engage in a P···D Noncovalent Interaction J. Phys. Chem. A 2011, 115, 11101-11110
31. 3 (X=F, OH, CN, NC, and FCC) ChemPhysChem 2012, 13, 1205-1212
32. 2X (X = P and As) and HM (M = ZnH, BeH, MgH, Li, and Na) J. Phys. Chem. A 2012, 116, 2547-2553
33. 3 with Neutral Ambidentate Electron Donor and Acceptor Molecules Phys. Chem. Chem. Phys. 2011, 13, 674-683
34. 2, OH, F, Cl) J. Phys. Chem. A 2011, 115, 13724-13731
35. 31P Spin-Spin Coupling Constants for Pnicogen Homodimers Chem. Phys. Lett. 2011, 512, 184-187
36. Alkorta, I.; Sánchez-Sanz, G.; Elguero, J.; Del Bene, J. E. Influence of Hydrogen Bonds on the P···P Pnicogen Bond J. Chem. Theory Comput. 2012, 8, 2320-2327
37. 3, NC J. Phys. Chem. A 2012, 116, 3056-3060
38. Del Bene, J. E.; Alkorta, I.; Sánchez-Sanz, G.; Elguero, J. Interplay of F-H···F Hydrogen Bonds and P···N Pnicogen Bonds J. Phys. Chem. A 2012, 116, 9205-9213
39. 3, NC: To What Extent Do They Differ? Chem. Phys. Lett. 2012, 538, 14-18
40. 2NX) with Ammonia J. Phys. Chem. A 2012, 116, 5199-5206
41. 2 J. Phys. Chem. A 2013, 117, 4981-4987
42. 2 Potential Surfaces: Hydrogen Bonds or Pnicogen Bonds? J. Phys. Chem. A 2013, 117, 183-191
43. Del Bene, J. E.; Alkorta, I.; Sánchez-Sanz, G.; Elguero, J. Phosphorus as a Simultaneous Electron-Pair Acceptor in Intermolecular P···N Pnicogen Bonds and Electron-Pair Donor to Lewis Acids J. Phys. Chem. A 2013, 117, 3133-3141
44. Grabowski, S. J.; Alkorta, I.; Elguero, J. Complexes between Dihydrogen and Amine, Phosphine, and Arsine Derivatives. Hydrogen Bond versus Pnictogen Interaction J. Phys. Chem. A 2013, 117, 3243-3251
45. n-PHF (n=2-6) Systems ChemPhysChem 2013, 14, 1656-1665
46. Bauza, A.; Quinonero, D.; Deya, P. M.; Frontera, A. Pnicogen-p Complexes: Theoretical Study and Biological Implications Phys. Chem. Chem. Phys. 2012, 14, 14061-14066
47. Bauzá, A.; Alkorta, I.; Frontera, A.; Elguero, J. On the Reliability of Pure and Hybrid DFT Methods for the Evaluation of Halogen, Chalcogen, and Pnicogen Bonds Involving Anionic and Neutral Electron Donors J. Chem. Theory Comput. 2013, 9, 5201-5210
48. Bauza, A.; Quinonero, D.; Deya, P. M.; Frontera, A. Halogen Bonding versus Chalcogen and Pnicogen Bonding: A Combined Cambridge Structural Database and Theoretical Study CrystEngComm 2013, 15, 3137-3144
49. 2X (X = F, Cl) with Nitrogen Bases J. Phys. Chem. A 2013, 117, 10497-10503
50. 2 J. Phys. Chem. A 2013, 117, 6893-6903
51. Politzer, P.; Murray, J. S.; Clark, T. Halogen Bonding and Other s-Hole Interactions: A Perspective Phys. Chem. Chem. Phys. 2013, 15, 11178-11189
52. Eskandari, K.; Mahmoodabadi, N. Pnicogen Bonds: A Theoretical Study Based on the Laplacian of Electron Density J. Phys. Chem. A 2013, 117, 13018-13024
53. Schiesser, C.; Wild, L. Homolytic Substitution at Phosphorus: An Ab Initio Study of the Reaction of Hydrogen Atom and Methyl Radical with Phosphine and Methylphosphine Aust. J. Chem. 1995, 48, 175-184
54. Buchanan, J. W.; Hanrahan, R. J. The Use of Phosphine as a Free Radical Scavenger in the Radiolysis of Methyl Iodide Vapor Radiat. Res. 1970, 44, 305-312
55. Dunning, T. H. Gaussian-Basis Sets for Use in Correlated Molecular Calculations. 1. The Atoms Boron through Neon and Hydrogen J. Chem. Phys. 1989, 90, 1007-1023
56. Woon, D. E.; Dunning, T. H. Gaussian Basis Sets for Use in Correlated Molecular Calculations. V. Core-Valence Basis Sets for Boron through Neon J. Chem. Phys. 1995, 103, 4572-4585
57. 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; Gaussian, Inc.: Wallingford, CT, 2009.
58. Bartlett, R. J.; Purvis, G. D. Many-Body Perturbation Theory, Coupled-Pair Many-Electron Theory, and the Importance of Quadruple Excitations for the Correlation Problem Int. J. Quantum Chem. 1978, 14, 561-581
59. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. Quadratic Configuration Interaction. A General Technique for Determining Electron Correlation Energies J. Chem. Phys. 1987, 87, 5968-5975
60. Werner, H.-J.; Knowles, P. J.; Manby, F. R.; Schütz, M.; Celani, P.; Knizia, G.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; MOLPRO 2012.1; Cardiff, U.K., 2010.
61. Su, P.; Li, H. Energy Decomposition Analysis of Covalent Bonds and Intermolecular Interactions J. Chem. Phys. 2009, 131, 014102
62. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
63. Jmol: An Open-Source Java Viewer for Chemical Structures in 3D, version 13.0; http://www.jmol.org/ (accessed Sept 26, 2013).
64. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
65. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Landis, C. R.; Weinhold, F. NBO-6; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2013.
66. Patek, M. Jmol NBO Visualization Helper; http://www.marcelpatek.com/nbo/ nbo.html (accessed Sept 26, 2013).
67. Keith, T. A. TK Gristmill Software, version 13.11.04; Overland Park, KS, 2013; http://aim.tkgristmill.com (accessed Dec 1, 2013).
68. Alkorta, I.; Picazo, O. Influence of Protonation on the Properties Derived from Electron Density ARKIVOC 2005, ix, 305-320
69. Zahn, S.; Frank, R.; Hey-Hawkins, E.; Kirchner, B. Pnicogen Bonds: A New Molecular Linker? Chem.-Eur. J. 2011, 17, 6034-6038
70. Cioslowski, J. Quantifying the Hammond Postulate: Intramolecular Proton Transfer in Substituted Hydrogen Catecholate Anions J. Am. Chem. Soc. 1991, 113, 6756-6760
71. Knop, O.; Boyd, R. J.; Choi, S. C. Sulfur-Sulfur Bond Lengths, or Can a Bond Length Be Estimated from a Single Parameter? J. Am. Chem. Soc. 1988, 110, 7299-7301
72. Alkorta, I.; Barrios, L.; Rozas, I.; Elguero, J. Comparison of Models to Correlate Electron Density at the Bond Critical Point and Bond Distance J. Mol. Struct.: THEOCHEM 2000, 496, 131-137
73. Alkorta, I.; Elguero, J. Fluorine-Fluorine Interactions: NMR and AIM Analysis Struct. Chem. 2004, 15, 117-120
74. Tang, T. H.; Deretey, E.; Knak Jensen, S. J.; Csizmadia, I. G. Hydrogen Bonds: Relation between Lengths and Electron Densities at Bond Critical Points Eur. Phys. J. D 2006, 37, 217-222
75. Mata, I.; Alkorta, I.; Molins, E.; Espinosa, E. Universal Features of the Electron Density Distribution in Hydrogen-Bonding Regions: A Comprehensive Study Involving H···X (X=H, C, N, O, F, S, Cl, π) Interactions Chem.-Eur. J. 2010, 16, 2442-2452
76. Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. From Weak to Strong Interactions: A Comprehensive Analysis of the Topological and Energetic Properties of the Electron Density Distribution Involving X- H···F-Y Systems J. Chem. Phys. 2002, 117, 5529-5542