Molecular tuning of the closed shell C-H⋯F-C hydrogen bond

Journal of Physical Chemistry A

Volumn 117, Issue 34, 2013, Pages 8256-8262

  Lu, Norman ^a,b   Ley, Rebecca M ^a   Cotton, Charles E ^a   Chung, Wei Cheng ^b   Francisco, Joseph S ^a,c   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CLOSED SHELLS; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; GASPHASE; H-BONDING; H-BONDING SYSTEMS; WEAK INTERACTIONS;

FUNCTIONAL GROUPS;

HYDROGEN BONDS;

CARBON; FLUORINE; HYDROGEN;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; ELECTRON; HYDROGEN BOND; THERMODYNAMICS;

CARBON; ELECTRONS; FLUORINE; HYDROGEN; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 84883414871     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp404791g     Document Type: Conference Paper

References (29)

1. Desiraju, G. R. and Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: New York, 1999.
2. 2, is Stabilized by C-H⋯N Bonds: Are There any Real Precedents? Chem. Commun. 1997, 17, 1673-1674
3. Zhao, X.; Wang, X.-Z.; Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. Hydrazide-Based Quadruply Hydrogen-Bonded Heterodimers. Structure, Assembling Selectivity, and Supramolecular Substitution J. Am. Chem. Soc. 2003, 125, 15128-15139
4. Tatamitani, Y.; Liu, B.; Shimada, J.; Ogata, T.; Ottaviani, P.; Maris, A.; Caminati, W.; Alonso, J. L. Weak, Improper, C-O⋯H-C Hydrogen Bonds in the Dimethyl Ether Dimer J. Am. Chem. Soc. 2002, 124, 2739-2743
5. López, J. C.; Caminati, W.; Alonso, J. L. The C-H⋯π Hydrogen Bond in the Benzene-Trifluoromethane Adduct: A Rotational Study Angew. Chem., Int. Ed. 2006, 45, 290-293
6. Lee, H.; Knobler, C. B.; Hawthorne, M. F. Supramolecular Self-assembly Directed by Carborane C-H⋯F Interactions Chem. Commun. 2000, 24, 2485-2486
7. Takahashi, S.; Jukurogi, T.; Katagiri, T.; Uneyama, K. Supramolecular Self-assembly Directed by Carborane C-H⋯F Interactions Isomorphic Supramolecular Structures via One-dimensional Hydrogen Bonding Motifs in Crystals of Chiral Difluorolactates, Trichlorolactates and Trifluorolactates CrystEngComm 2006, 8, 320-326
8. Caminati, W.; Melandri, S.; Moreschini, P.; Favero, P. G. The C-F⋯H-C "Anti-Hydrogen Bond" in the Gas Phase: Microwave Structure of the Difluoromethane Dimer Angew. Chem., Int. Ed. 1999, 38, 2924-2925
9. 4 J. Am. Chem. Soc. 2002, 124, 11854-11855
10. Alonso, J. L.; Antolínez, S.; Blanco, S.; Lesarri, A.; López, J. C.; Caminati, W. Weak C-H⋯O and C-H⋯F-C Hydrogen Bonds in the Oxirane-Trifluoromethane Dimer J. Am. Chem. Soc. 2004, 126, 3244-3249
11. Matsuura, H.; Yoshida, H.; Hieda, M.; Shin-ya Yamanaka, S.; Harada, T.; Shin-ya, K.; Ohno, K. Experimental Evidence for Intramolecular Blue-Shifting C-H⋯O Hydrogen Bonding by Matrix-Isolation Infrared Spectroscopy J. Am. Chem. Soc. 2003, 125, 13910-13911
12. 2 Where M = Pt, Pd CrystEngComm 2010, 12, 538-542
13. Dixon, D. A.; Smart, B. E. In Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; Chapter 2, pp 18-35.
14. α-H⋯Oî-C Hydrogen Bond? J. Am. Chem. Soc. 2000, 122, 4750-4755
15. Scheiner, S.; Kar, T. Spectroscopic and Structural Signature of the CH-O Hydrogen Bond J. Phys. Chem. A 2008, 112, 11854-11860
16. Scheiner, S.; Kar, T.; Pattanayak, J. Comparison of Various Types of Hydrogen Bonds Involving Aromatic Amino Acids J. Am. Chem. Soc. 2002, 124, 13257-13264
17. Scheiner, S.; Kar, T. Analysis of the Reactivities of Protein C-H Bonds to H Atom Abstraction by OH Radical J. Am. Chem. Soc. 2010, 132, 16450-16459
18. Hobza, P.; Havlas, Z. Blue-Shifting Hydrogen Bonds Chem. Rev. 2000, 100, 4253-4264
19. Hof, F.; Diederich, F. Medicinal Chemistry in Academia: Molecular Recognition with Biological Receptors Chem. Commun. 2004, 5, 477-487
20. Kryachko, E.; Scheiner, S. CH⋯F Hydrogen Bonds. Dimers of Fluoromethanes J. Phys. Chem. A 2004, 108, 2527-2535
21. Takahashi, O.; Yamasaki, K.; Kohno, Y.; Ueda, K.; Suezawa, H.; Nishio, M. Origin of the Gauche Preference of n -Propyl Halides and Related Molecules Investigated by ab Initio MO Calculations: Importance of the CH/ n Hydrogen Bond Chem. Phys. Lett. 2007, 440, 64-67
22. 3CH Chem. Phys. Lett. 2007, 441, 194-197
23. Michielsen, B.; Herrebout, W. A.; van der Veken, B. J. C-H Bonds with a Positive Dipole Gradient can Form Blue-shifting Hydrogen Bonds: the Complex of Halothane with Methyl Fluoride ChemPhysChem 2008, 9, 1693-1701
24. Leung, H. O.; Marshall, M. D.; Drake, T. L.; Pudlik, T.; Savji, N.; McCune, D. W. Fourier Transform Microwave Spectroscopy and Molecular Structure of the 1,1-Difluoroethylene-hydrogen Fluoride Complex J. Chem. Phys. 2009, 131, 204301
25. Pluháčková, K.; Hobza, P. On the Nature of the Surprisingly Small (Red) Shift in the Halothane⋯Acetone Complex ChemPhysChem 2007, 8, 1352-1356
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, A., M.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
27. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.9; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2009.
28. Rowland, R. S.; R. Taylor, R. Intermolecular Nonbonded Contact Distances in Organic Crystal Structures: Comparison with Distances Expected from van der Waals Radii J. Phys. Chem. 1996, 100, 7384-7391 (The value of 2.54 Å has been used here, but the use of Pauling and Bondi radii gives values of 2.55 and 2.67 Å, respectively)
29. Lu, N. who spent his sabbatical leave at Chemistry Department, Purdue University thanks the National Science Council of Taiwan (100-2918-I-027-001) and National Taipei University of Technology for the financial support.