Cl(-) exchange SN2 reaction inside carbon nanotubes: C-H⋯π and Cl⋯π interactions govern the course of the reaction

Journal of Physical Chemistry C

Volumn 118, Issue 9, 2014, Pages 5032-5040

  Giacinto, Pietro ^a   Bottoni, Andrea ^a   Calvaresi, Matteo ^a   Zerbetto, Francesco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; ASYMPTOTIC VALUES; AUGMENTED BARRIER; CHEMICAL PROCESS; INTRINSIC REACTION; QUANTUM MECHANICAL; STRUCTURAL DISTORTIONS; TRANSITION STATE;

CARBON NANOTUBES; GASES; QUANTUM THEORY; TUBES (COMPONENTS);

CHLORINE COMPOUNDS;

EID: 84897731479     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp412456q     Document Type: Article

References (64)

1. Miners, S. A.; Rance, G. A.; Khlobystov, A. N. Regioselective Control of Aromatic Halogenation Reactions in Carbon Nanotube Nanoreactors Chem. Commun. 2013, 49, 5586-5588
2. Molecular Encapsulation: Organic Reactions in Constrained Systems; Brinker, U. H.; Mieusset, J.-L., Eds.; Wiley: New York, 2010.
3. Santiso, E. E.; George, A. M.; Turner, C. H.; Kostov, M. K.; Gubbins, K. E.; Buongiorno-Nardelli, M.; Sliwinska-Bartkowiak, M. Adsorption and Catalysis: The Effect of Confinement on Chemical Reactions Appl. Surf. Sci. 2005, 252, 766-777
4. Pederson, M. R.; Broughton, J. Q. Nanocapillarity in Fullerene Tubules Phys. Rev. Lett. 1992, 69, 2689-2692
5. Khlobystov, A. N.; Britz, D. A.; Briggs, G. A. D. Molecules in Carbon Nanotubes Acc. Chem. Res. 2005, 38, 901-909
6. Khlobystov, A. N. Carbon Nanotubes: From Nano Test Tube to Nano-Reactor ACS Nano 2011, 5, 9306-9312
7. Britz, D. A.; Khlobystov, A. N. Noncovalent Interactions of Molecules with Single Walled Carbon Nanotubes Chem. Soc. Rev. 2006, 35, 637-659
8. 78 Inside Carbon Nanotubes Nano Lett. 2005, 5, 349-355
9. Guan, L.; Suenaga, K.; Shi, Z.; Gu, Z.; Iijima, S. Polymorphic Structures of Iodine and Their Phase Transition in Confined Nanospace Nano Lett. 2007, 7, 1532-1535
10. Takenobu, T.; Takano, T.; Shiraishi, M.; Murakami, Y.; Ata, M.; Kataura, H.; Achiba, Y.; Iwasa, Y. Stable and Controlled Amphoteric Doping by Encapsulation of Organic Molecules Inside Carbon Nanotubes Nat. Mater. 2003, 2, 683-688
11. Plank, W.; Pfeiffer, R.; Schaman, C.; Kuzmany, H.; Calvaresi, M.; Zerbetto, F.; Meyer, J. Electronic Structure of Carbon Nanotubes with Ultrahigh Curvature ACS Nano 2010, 4, 4515-4522
12. Liu, X.; Kuzmany, H.; Ayala, P.; Calvaresi, M.; Zerbetto, F.; Pichler, T. Selective Enhancement of Photoluminescence in Filled Single-Walled Carbon Nanotubes Adv. Funct. Mater. 2012, 22, 3202-3208
13. Wang, W.; Wang, D.; Zhang, Y.; Ji, B.; Tian, A. Hydrogen Bond and Halogen Bond Inside the Carbon Nanotube J. Chem. Phys. 2011, 134, 054317
14. Santiso, E. E.; Buongiorno Nardelli, M.; Gubbins, K. E. A Remarkable Shape-Catalytic Effect of Confinement on the Rotational Isomerization of Small Hydrocarbons J. Chem. Phys. 2008, 128, 034704
15. Feng, H.; Qian, Z.; Wang, C.; Chen, C.; Chen, J. Tuning the Energy Barrier of Water Exchange Reactions on Al(III) by Interaction with the Single-Walled Carbon Nanotubes Dalton Trans. 2011, 40, 4183-4189
16. Wang, L.; Yi, C.; Zou, H.; Gan, H.; Xu, J.; Xu, W. Initial Reactions of Methyl-Nitramine Confined Inside Armchair (5,5) Single-Walled Carbon Nanotube J. Mol. Model. 2011, 17, 2751-2758
17. Wang, L.; Yi, C.; Zou, H.; Xu, J.; Xu, W. On the Isomerization and Dissociation of Nitramide Encapsulated Inside an Armchair (5,5) Single-Walled Carbon Nanotube Mater. Chem. Phys. 2011, 127, 232-238
18. Mann, D. J.; Halls, M. D. Water Alignment and Proton Conduction Inside Carbon Nanotubes Phys. Rev. Lett. 2003, 90, 195503
19. Zoete, V.; Meuwly, M. On the Influence of Semirigid Environments on Proton Transfer Along Molecular Chains J. Chem. Phys. 2004, 120, 7085-7094
20. Santiso, E. E.; George, A. M.; Gubbins, K. E.; Buongiorno Nardelli, M. Effect of Confinement by Porous Carbons on the Unimolecular Decomposition of Formaldehyde J. Chem. Phys. 2006, 125, 084711
21. Trzaskowski, B.; Adamowicz, L. Chloromethane and Dichloromethane Decompositions Inside Nanotubes as Models of Reactions in Confined Space Theor. Chem. Acc. 2009, 124, 95-103
22. Wang, L.; Yi, C.; Zou, H.; Xu, J.; Xu, W. Rearrangement and Thermal Decomposition of Nitromethane Confined Inside an Armchair (5, 5) Single-Walled Carbon Nanotube Chem. Phys. 2010, 367, 120-126
23. Wang, L.; Xu, J.; Yi, C.; Zou, H.; Xu, W. Theoretical Study on the Thermal Decomposition of Nitromethane Encapsulated Inside Single-Walled Carbon Nanotubes J. Mol. Struct. (Theochem) 2010, 940, 76-81
24. Halls, M. D.; Schlegel, H. B. Chemistry Inside Carbon Nanotubes: the Menshutkin SN2 Reaction J. Phys. Chem. B 2002, 106, 1921-1925
25. N2 Reaction Nano Lett. 2005, 5, 1861-1866
26. 2 → HD + H Reaction J. Phys. Chem. C 2008, 112, 2654-2659
27. 2 → HD + H Reaction Confined in Carbon Nanotubes: Parallel Trajectories J. Phys. Chem. C 2008, 112, 15260-15266
28. 2 → HD + H Reaction Confined in Carbon Nanotubes: Effects of Collisions with the Nanotube Walls J. Phys. Chem. C 2010, 114, 9030-9040
29. N2 Reaction within Pristine and Stone-Wales Defective BNNTs and CNTs J. Phys. Chem. C 2013, 117, 5095-5100
30. Pan, X.; Fan, Z.; Chen, W.; Ding, Y.; Luo, H.; Bao, X. Enhanced Ethanol Production Inside Carbon-Nanotube Reactors Containing Catalytic Particles Nat. Mater. 2007, 6, 507-511
31. Pan, X.; Bao, X. Reactions Over Catalysts Confined in Carbon Nanotubes Chem. Commun. 2008, 47, 6271-6281
32. Serp, P.; Castillejos, E. Catalysis in Carbon Nanotubes ChemCatChem 2010, 2, 41-47
33. Pan, X.; Bao, X. The Effects of Confinement inside Carbon Nanotubes on Catalysis Acc. Chem. Res. 2011, 44, 553-562
34. Su, D. S.; Perathoner, S.; Centi, G. Nanocarbons for the Development of Advanced Catalysts Chem. Rev. 2013, 113, 5782-5816
35. Chen, Z.; Nagase, S.; Hirsch, A.; Haddon, R. C.; Thiel, W.; Schleyer, P. van R. Side-Wall Opening of Single-Walled Carbon Nanotubes (SWCNTs) by Chemical Modification: A Critical Theoretical Study Angew.Chem., Int. Ed. 2004, 43, 1552-1554
36. Vreven, T.; Morokuma, K.; Farkas, Ö.; Schlegel, H. B.; Frisch, M. J. Geometry Optimization with QM/MM, ONIOM and other Combined Methods. I. Micro-Iterations and Constraints J. Comput. Chem. 2003, 24, 760-769
37. Humphrey, W.; Dalke, A.; Schulten, K. VMD-Visual Molecular Dynamics J. Mol. Graphics 1996, 14, 33-38
38. 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.
39. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
40. 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, 215-241
41. Binkley, J. S.; Pople, J. A.; Hehre, W. J. Self-Consistent Molecular Orbital Methods. 21. Small Split-Valence Basis Sets for First-Row Elements J. Am. Chem. Soc. 1980, 102, 939-947
42. Ditchfield, R.; Hehre, W. J.; Pople, J. A. Self-Consistent Molecular Orbital Methods. 9. Extended Gaussian-Type Basis for Molecular-Orbital Studies of Organic Molecules J. Chem. Phys. 1971, 54, 724-728
43. Vreven, T.; Byun, K. S.; Komáromi, I.; Dapprich, S.; Montgomery, J. A., Jr.; Morokuma, K.; Frisch, M. J. Combining Quantum Mechanics Methods with Molecular Mechanics Methods in ONIOM J. Chem. Theory Comput. 2006, 2, 815-826
44. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F. AM1: A New General Purpose Quantum Mechanical Molecular Model J. Am. Chem. Soc. 1985, 107, 3902-3909
45. Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods. I. Method J. Comput. Chem. 1989, 10, 209-220
46. Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods. V. Modification of NDDO Approximations and Application to 70 Elements J. Mol. Model. 2007, 13, 1173-1213
47. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. UFF, a Full Periodic-Table Force-Field for Molecular Mechanics and Molecular-Dynamics Simulations J. Am. Chem. Soc. 1992, 114, 10024-10035
48. Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III Dreiding-A Generic Force-Field for Molecular Simulations J. Phys. Chem. 1990, 94, 8897-8909
49. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A Second Generation Force-Field for the Simulation of Proteins, Nucleic-Acids, and Organic-Molecules J. Am. Chem. Soc. 1995, 117, 5179-5197
50. Rappé, A. K.; Goddard, W. A., III Charge Equilibration for Molecular-Dynamics Simulations J. Phys. Chem. 1991, 95, 3358-3363
51. Barlow, S. E.; van Doren, J. M.; Bierbaum, V. M. The Gas Phase Displacement Reaction of Chloride Ion with Methyl Chloride as a Function of Kinetic Energy J. Am. Chem. Soc. 1988, 110, 7240-7242
52. Li, C.; Ross, P.; Szulejko, J. E.; McMahon, T. B. High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase SN2 Reactions J. Am. Chem. Soc. 1996, 118, 9360-9367
53. - (X,Y = F,Cl,Br). Validation of Hybrid DFT Methods J. Phys. Chem. A 2001, 105, 895-904
54. N2 Reactions at Saturated Carbon Chem. Phys. Lett. 1996, 260, 558-564
55. N2@Si) J. Comput. Chem. 2005, 26, 1497-1504
56. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167
57. Karthikeyan, S.; Ramanathan, V.; Mishra, B. K. Influence of the Substituents on the CH...π Interaction: Benzene-Methane Complex J. Phys. Chem. A 2013, 117 (30) 6687-6694
58. Forni, A.; Pieraccini, S.; Rendine, S.; Sironi, M. Halogen Bonds with Benzene: An Assessment of DFT Functionals J. Comput. Chem. 2014, 35, 386-394
59. Janowsky, T.; Pulay, P. High Accuracy Benchmark Calculations on the Benzene Dimer Potential Energy Surface Chem. Phys. Lett. 2007, 447, 27-32
60. Pitoňák, M.; Neogrády, P.; Rĕ záč, J.; Jurečka, P.; Urban, M.; Hobza, P. Benzene Dimer: High-Level Wave Function and Density Functional Theory Calculations J. Chem. Theory Comput. 2008, 4, 1829-1834
61. Sinnokrot, M. O.; Sherill, C. D. High-Accuracy Quantum Mechanical Studies of π-π Interactions in Benzene Dimers J. Phys. Chem. A 2006, 110, 10656-10668
62. Prasanna, M. D.; Guru Row, T. N. C-Halogen - -π Interactions and Their Influence on Molecular Conformation and Crystal Packing: A Database Study Cryst. Eng. 2000, 3, 135-154
63. Saraogi, I.; Vijay, V. G.; Soma, D.; Sekar, K.; Guru Row, T. N. C-Halogen...π Interactions in Proteins: A Database Study Cryst. Eng. 2003, 6, 69-77
64. Imai, Y. N.; Inoue, Y.; Nakanishi, I.; Kitaura, K. Cl-π Interactions in Protein-Ligand Complexes Protein Sci. 2008, 17, 1129-1137