The pnicogen bond: Its relation to hydrogen, halogen, and other noncovalent bonds

Accounts of Chemical Research

Volumn 46, Issue 2, 2013, Pages 280-288

  Scheiner, Steve ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN; NITROGEN; PHOSPHORUS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; THERMODYNAMICS;

HALOGENS; HYDROGEN BONDING; MODELS, MOLECULAR; NITROGEN; PHOSPHORUS; THERMODYNAMICS;

EID: 84874102873     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar3001316     Document Type: Article

References (50)

1. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
2. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
3. Gilli, G.; Gilli, P. The Nature of the Hydrogen Bond; Oxford University Press: Oxford, U.K., 2009.
4. 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
5. Girolami, G. S. Origin of the terms pnictogen and pnictide J. Chem. Educ. 2009, 86, 1200-1201
6. Scheiner, S. A new noncovalent force: Comparison of P·· ·N Interaction with hydrogen and halogen bonds J. Chem. Phys. 2011, 134, 094315
7. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An overview of halogen bonding J. Mol. Model. 2007, 13, 305-311
8. Scheiner, S. On the properties of X···N noncovalent interactions for first-, second- and third-row X atoms J. Chem. Phys. 2011, 134, 164313
9. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Halogen bonding based recognition processes: A world parallel to hydrogen bonding Acc. Chem. Res. 2005, 38, 386-395
10. Politzer, P.; Murray, J. S.; Clark, T. Halogen bonding: An electrostatically-driven highly directional noncovalent interaction Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
11. Legon, A. C. The halogen bond: an interim perspective Phys. Chem. Chem. Phys. 2010, 12, 7736-7747
12. Iwaoka, M.; Takemoto, S.; Tomoda, S. Statistical and theoretical investigations on the directionality of nonbonded S···O interactions. Implications for molecular design and protein engineering J. Am. Chem. Soc. 2002, 124, 10613-10620
13. Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. Blue shifts vs red shifts in σ-hole bonding J. Mol. Model. 2008, 14, 699-704
14. Scheiner, S. Weak H-bonds. Comparisons of CH···O to NH···O in proteins and PH···N to direct P···N interactions Phys. Chem. Chem. Phys. 2011, 13, 13860-13872
15. Murray, J. S.; Lane, P.; Clark, T.; Politzer, P. σ-hole bonding: molecules containing group VI atoms J. Mol. Model. 2007, 13, 1033-1038
16. Murray, J. S.; Lane, P.; Politzer, P. A predicted new type of directional noncovalent interaction Int. J. Quantum Chem. 2007, 107, 2286-2292
17. Palusiak, M. On the nature of halogen bond-The Kohn-Sham molecular orbital approach J. Mol. Struct.: THEOCHEM 2010, 945, 89-92
18. Zierkiewicz, W.; Michalska, D.; Zeegers-Huyskens, T. Theoretical investigation of the conformation, acidity, basicity and hydrogen bonding ability of halogenated ethers Phys. Chem. Chem. Phys. 2010, 12, 13681-13691
19. Hobza, P.; Muller-Dethlefs, K. Non-Covalent Interactions; RSC: Cambridge, 2010.
20. Scheiner, S. Effects of substituents upon the P···N noncovalent interaction: The limits of its strength J. Phys. Chem. A 2011, 115, 11202-11209
21. Scheiner, S. Can two trivalent N atoms engage in a direct N···N noncovalent interaction? Chem. Phys. Lett. 2011, 514, 32-35
22. Adhikari, U.; Scheiner, S. The S···N noncovalent interaction: Comparison with hydrogen and halogen bonds Chem. Phys. Lett. 2011, 514, 36-39
23. Gu, Y.; Kar, T.; Scheiner, S. Fundamental properties of the CH···O interaction: Is it a true hydrogen bond? J. Am. Chem. Soc. 1999, 121, 9411-9422
24. Gu, Y.; Kar, T.; Scheiner, S. Evaluation of the H-bonding properties of CH···O interactions based upon NMR spectra J. Mol. Struct.: THEOCHEM 2000, 500, 441-452
25. Scheiner, S. Effects of multiple substitution upon the P···N noncovalent interaction Chem. Phys. 2011, 387, 79-84
26. Adhikari, U.; Scheiner, S. Effects of carbon chain substituent on the P···N noncovalent bond Chem. Phys. Lett. 2012, 536, 30-33
27. Zahn, S.; Frank, R.; Hey-Hawkins, E.; Kirchner, B. Pnicogen bonds: A new molecular linker? Chem.-Eur. J. 2011, 17, 6034-6038
28. 31P spin-spin coupling constants for pnicogen homodimers Chem. Phys. Lett. 2011, 512, 184-187
29. 3, NC J. Phys. Chem. A 2012, 116, 3056-3060
30. Politzer, P.; Murray, J. S.; Concha, M. σ-hole bonding between like atoms; a fallacy of atomic charges J. Mol. Model. 2008, 14, 659-665
31. 2, OH, F, Cl) J. Phys. Chem. A 2011, 115, 13724-13731
32. 3 (E = Pnictogen, X = Halogen) Inorg. Chem. 2009, 48, 6740-6747
33. Adhikari, U.; Scheiner, S. Substituent effects on Cl·· ·N, S···N, and P···N noncovalent bonds J. Phys. Chem. A 2012, 116, 3487-3497
34. 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
35. Burley, S. K.; Petsko, G. A. Amino-aromatic interactions in proteins FEBS Lett. 1986, 203, 139-143
36. Zwier, T. C. Laser spectroscopy of jet-cooled biomolecules and their water-containing clusters: Water bridges and molecular conformation J. Phys. Chem. A 2001, 105, 8827-8839
37. Adhikari, U.; Scheiner, S. Comparison of P···D (D = P, N) with other noncovalent bonds in molecular aggregates J. Chem. Phys. 2011, 135, 184306
38. Bushuk, S. B.; Carre, F. H.; Guy, D. M. H.; Douglas, W. E.; Kalvinkovskya, Y. A.; Klapshina, L. G.; Rubinov, A. N.; Stupak, A. P.; Bushuk, B. A. Hypercoordinate silicon and phosphorus acetylene compounds: crystal structure determinations and fluorescence spectroscopic study Polyhedron 2004, 23, 2615-2623
39. Tschirschwitz, S.; Lönnecke, P.; Hey-Hawkins, E. Aminoalkylferrocenyldichlorophosphanes: facile synthesis of versatile chiral starting materials Dalton Trans. 2007, 2007, 1377-1382
40. Muller, G.; Brand, J.; Jetter, S. E. Donor-acceptor complexes between organoamines and phosphorus tribromide Z. Naturforsch., B: J. Chem. Sci. 2001, 56, 1163-1171
41. Kilian, P.; Slawin, A. M. Z.; Woollins, J. D. Naphthalene-1,8-diyl bis(halogenophosphanes): Novel syntheses and structures of useful synthetic building blocks Chem.-Eur. J. 2003, 9, 215-222
42. 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
43. 2 and the effect of phosphine modifiers on hydrogen transfer catalysis Organometallics 2007, 26, 2659-2671
44. 4OMe-o): Synthesis, derivatization, group 10 and 11 metal complexes and catalytic investigations. DFT calculations on intermolecular P···P interactions in halo-phosphines Inorg. Chem. 2008, 47, 7035-7047
45. 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, 2009, 2776-2788
46. Bühl, M.; Kilian, P.; Woollins, J. D. Prediction of a new delocalised bonding motif between group 15 or group 16 atoms ChemPhysChem 2011, 12, 2405-2408
47. 2 Acta Crystallogr. 1975, B34, 1367-1372
48. 2, X = F, Cl, Br, I) J. Organomet. Chem. 1996, 524, 253-261
49. Wallis, J. D.; Easton, R. J. C.; Dunitz, J. D. Interactions between Functional Groups Part IV. The responses of four diazonium groups to adjacent electron-rich atoms in peri-substituted naphthalene and quinoline derivatives Helv. Chim. Acta 1993, 76, 1411-1424
50. Adhikari, U.; Scheiner, S. Sensitivity of pnicogen, chalcogen, halogen and H-bonds to angular distortions Chem. Phys. Lett. 2012, 532, 31-35