Solvent-induced red-shifts for the proton stretch vibrational frequency in a hydrogen-bonded complex. 1. A valence bond-based theoretical approach

Journal of Physical Chemistry B

Volumn 118, Issue 28, 2014, Pages 8330-8351

  Kiefer, Philip M ^a   Pines, Ehud ^b   Pines, Dina ^b   Hynes, James T ^a,c  

^a UNIVERSITY OF COLORADO   (United States)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^c ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALGORITHMS; DIPOLE MOMENT; ELECTRONIC STRUCTURE; HYDROGEN BONDS;

GROUND VIBRATIONAL STATE; H-BONDED COMPLEXES; HYDROGEN-BONDED COMPLEXES; NON-POLAR SOLVENTS; SOLVENT COORDINATES; SOLVENT DEPENDENCE; SOLVENT STABILIZATION; THEORETICAL APPROACH;

SOLVENTS;

PROTON; SOLVENT;

CHEMISTRY; HYDROGEN BOND; THEORETICAL MODEL; VIBRATION;

HYDROGEN BONDING; MODELS, THEORETICAL; PROTONS; SOLVENTS; VIBRATION;

EID: 84904546376     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp501815j     Document Type: Article

References (124)

1. Bell, R. P. The Proton in Chemistry, 2 nd ed.; Cornell University Press: Ithaca, NY, 1973.
2. Caldin, E.; Gold, V. Proton Transfer Reactions; Chapman and Hall: London, 1975.
3. Hynes, J. T., Klinman, J. P., Limbach, H. H., Schowen, R. L., Eds. Hydrogen-Transfer Reactions; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2007.
4. Elsaesser, T., Bakker, H. J., Eds. Ultrafast Hydrogen Bonding Dynamics and Proton Transfer Processes in the Condensed Phase; Kluwer Academic Publishers: Amsterdam, 2002.
5. Hibbert, F. Mechanisms of Proton Transfer between Oxygen and Nitrogen Acids and Bases in Aqueous Solution Adv. Phys. Org. Chem. 1986, 22, 113-212
6. Hibbert, F.; Emsley, J. Hydrogen Bonding and Chemical Reactivity Adv. Phys. Org. Chem. 1990, 26, 255-379
7. Pimentel, G. C. The Hydrogen Bond; W. H. Freeman: San Francisco, 1960.
8. Novak, A. Hydrogen Bonding in Solids: Correlation of Spectroscopic and Crystallographic Data Struct. Bonding (Berlin, Ger.) 1974, 18, 177-216
9. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker, Inc.: New York, 1974.
10. Fersht, A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding; W.H. Freeman: New York, 1999.
11. Cleland, W. W.; Kreevoy, M. M. Low-Barrier Hydrogen Bonds and Enzymic Catalysis Science 1994, 264, 1887-1890
12. Cleland, W. W.; Frey, P. A.; Gerlt, J. A. The Low Barrier Hydrogen Bond in Enzymatic Catalysis J. Biol. Chem. 1998, 273, 25529-25532
13. Kamlet, M. J.; Solomonovici, A.; Taft, R. W. Linear Solvation Energy Relationships. 5. Correlations between Infrared Δν Values and the π Scale of Hydrogen Bond Acceptor Basicities J. Am. Chem. Soc. 1979, 101, 3734-3739
14. a) J. Chem. Soc., Perkin Trans. 2 1985, 1583-1589
15. Kamlet, M. J.; Abboud, J. L.; Taft, R. W. The Solvatochromic Comparison Method. 6. The π* Scale of Solvent Polarities J. Am. Chem. Soc. 1977, 99, 6027-6038
16. Taft, R. W.; Abboud, J. L.; Kamlet, M. J. Linear Solvation Energy Relationships. 23. A Comprehensive Collection of the Solvatochromic Paramaters, π*, α, and β, and Some Methods for Simplifying the Generalized Solvatochromic Equation J. Org. Chem. 1984, 49, 2001-2005
17. Taft, R. W.; Abboud, J. L.; Kamlet, M. J. Solvatochromic Comparison Method. 20. Linear Solvation Energy Relationships. 12. The δ Term in the Solvatochromic Equations J. Am. Chem. Soc. 1981, 103, 1080-1086
18. Kirkwood, J. G. Theory of Solutions of Molecules Containing Widely Separated Charges with Special Application to Zwitterions J. Chem. Phys. 1934, 2, 351-361
19. Keinan, S.; Pines, D.; Kiefer, P. M.; Hynes, J. T.; Pines, E. Solvent Induced O-H Vibration Red-Shifts in Hydrogen-Bonded Acid-Base Complexes. J. Chem. Phys. B, submitted for publication, 2014.
20. Bauer, P. E.; Magat, M. Sur la Déformation des Molécules en Phase Condensée et la liaison hydrogen J. Phys. Radium 1938, 9, 319-330
21. Onsager, L. Electric Moments of Molecules in Liquids J. Am. Chem. Soc. 1936, 58, 1486-1493
22. Böttcher, C. J. F. Theory of Electric Polarization; Elsevier: Amsterdam, 1952.
23. Buckingham, A. D. Solvent Effects in Infrared Spectroscopy Proc. R. Soc. London, Ser. A 1958, 248, 169-182
24. Pullin, A. D. E. The Variation of Infrared Vibration Frequencies with Solvent Spectrochim. Acta 1958, 13, 125-138
25. Pullin, A. D. E. Solution Frequency Shift and Solvent Refractive Index Spectrochim. Acta 1960, 16, 12-24
26. Rao, C. N. R.; Singh, S.; Senthilnathan, V. P. Spectroscopic Studies of Solute-Solvent Interactions Chem. Soc. Rev. 1976, 5, 297-316
27. Wong, M. H.; Wiberg, K. B.; Frisch, M. Hartree-Fock Second Derivatives and Electric Field Properties in a Solvent Reaction Field: Theory and Application J. Chem. Phys. 1991, 95, 8991-8998
28. Cappelli, C.; Mennucci, B.; da Silva, C. O.; Tomasi, J. Refinements on Solvation Continuum Models: Hydrogen-Bond Effects on the OH Stretch in Liquid Water and Methanol J. Chem. Phys. 2000, 112, 5382-5392
29. Cammi, R.; Cappelli, C.; Corni, S.; Tomasi, J. On the Calculation of Infrared Intensities in Solution within the Polarizable Continuum Model J. Phys. Chem. A 2000, 104, 9874-9879
30. Cappelli, C.; Corni, S.; Cammi, R.; Mennucci, B.; Tomasi, J. Nonequilibrium formulation of infrared frequencies and intensities in solution: Analytical evaluation within the polarizable continuum model J. Chem. Phys. 2000, 113, 11270-11279
31. van der Zwan, G.; Hynes, J. T. Time-Dependent Fluorescence Solvent Shifts, Dielectric Friction, and Nonequilibrium Solvation in Polar Solvents J. Phys. Chem. 1985, 89, 4181-4188
32. Asbury, J. B.; Wang, Y.; Lian, T. Time-Dependent Vibration Stokes Shift during Solvation: Experiment and Theory Bull. Chem. Soc. Jpn. 2002, 75, 973-983
33. Prémont-Schwarz, M.; Xiao, D.; Batista, V.; Nibbering, E. T. J. The O-H Stretching Mode of a Prototypical Photoacid as a Local Dielectric Probe J. Phys. Chem. A 2011, 115, 10511-10516
34. Xiao, D.; Prémont-Schwarz, M.; Batista, V.; Nibbering, E. T. J. Ultrafast Vibrational Frequency Shifts Induced by Electronic Excitations: Naphthols in Low Dielectric Media J. Phys. Chem. A 2011, 116, 2775-2790
35. Timoneda, J. J.; Hynes, J. T. Nonequilibrium Free Energy Surfaces for Hydrogen-Bonded Proton Transfer Complexes in Solution J. Phys. Chem. 1991, 95, 10431-10442
36. Kiefer, P. M.; Hynes, J. T. Theoretical Aspects of Proton Transfer Reactions in a Polar Environment. In Hydrogen-Transfer Reactions; Hynes, J. T.; Klinman, J. P.; Limbach, H. H.; Schowen, R. L., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2007, Vol. 1, pp 303-348.
37. Kiefer, P. M.; Hynes, J. T. Nonlinear Free Energy Relations for Adiabatic Proton Transfer Reactions in a Polar Environment. I. Fixed Proton Donor-Acceptor Distance J. Phys. Chem. A 2002, 106, 1834-1849
38. Kiefer, P. M.; Hynes, J. T. Nonlinear Free Energy Relations for Adiabatic Proton Transfer Reactions in a Polar Environment. II. Inclusion of Proton Donor-Acceptor Vibration J. Phys. Chem. A 2002, 106, 1850-1861
39. Thompson, W. H.; Hynes, J. T. Frequency Shifts in the Hydrogen-Bonded OH Stretch in Water-Halide Clusters. The Importance of Charge Transfer J. Am. Chem. Soc. 2000, 122, 6278-6286
40. 2 Pair in Low Polarity Solvents J. Phys. Chem. A 2001, 105, 2582-2590
41. Kiefer, P. M.; Hynes, J. T. Temperature-Dependent Solvent Polarity Effects on Adiabatic Proton Transfer Rate Constants and Kinetic Isotope Effects Isr. J. Chem. 2004, 44, 171-184
42. Allerhand, A.; von Schleyer, P. R. Solvent Effects in Infrared Spectroscopic Studies of Hydrogen Bonding J. Am. Chem. Soc. 1963, 85, 371-380
43. McDowell, S. A. C.; Buckingham, A. D. On the Correlation between Bond-Length Change and Vibrational Frequency Shift in Hydrogen-Bonded Complexes: A Computational Study of Y⋯HCl Dimers (Y = N2, CO, BF) J. Am. Chem. Soc. 2005, 127, 15515-15520
44. The importance of charge transfer for the proton stretch frequencies of gas phase H-bond clusters using a two VB model was emphasized in ref 38. See also Robertson, W. H.; Johnson, M. A. Molecular Aspects Of Halide Ion Hydration: The Cluster Approach Annu. Rev. Phys. Chem. 2003, 54, 173-213 For reviews on the charge transfer contribution to H-bond energies, see refs 44-46
45. Morokuma, K. Why do molecules interact? The origin of electron donor-acceptor complexes, hydrogen bonding, and proton affinity Acc. Chem. Res. 1977, 10, 294-300
46. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 1988, 88, 899-926
47. Ramos-Cordoba, E.; Lambrecht, D. S.; Head-Gordon, M. Charge-transfer and the hydrogen bond: Spectroscopic and structural implications from electronic structure calculations Faraday Discuss. 2011, 150, 345-362
48. McCoy, A. B. Diffusion Monte Carlo Approaches for Investigating the Structure and Vibrational Spectra of Fluxional Systems Int. Rev. Phys. Chem. 2006, 25, 77-107
49. Skinner, J.; Auer, B. M.; Lin, Y.-S. Vibrational Line Shapes, Spectral Diffusion, and Hydrogen Bonding in Liquid Water Adv. Chem. Phys. 2009, 142, 59-103
50. Bakker, H. J.; Skinner, J. L. Vibrational Spectroscopy as a Probe of Structure and Dynamics in Liquid Water Chem. Rev. 2010, 110, 1498-1517
51. Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents. Physical Properties and Methods of Purification, 4 th ed.; Techniques of Chemistry; John Wiley & Sons: New York, 1986.
52. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 1988.
53. Kim, H. J.; Hynes, J. T. Equilibrium and Nonequilibrium Solvation and Solute Electronic Structure. I. Formulation J. Chem. Phys. 1990, 93, 5194-5210
54. Kim, H. J.; Hynes, J. T. Equilibrium and Nonequilibrium Solvation and Solute Electronic Structure. II. Strong Coupling Limit J. Chem. Phys. 1990, 93, 5211-5223
55. Kim, H. J.; Hynes, J. T. Equilibrium and Nonequilibrium Solvation and Solute Electronic Structure. III. Quantum Theory J. Chem. Phys. 1992, 96, 5088-5110
56. Lee, S.; Hynes, J. T. Solution Phase Reaction Path Hamiltonian. I. Formulation J. Chem. Phys. 1988, 88, 6853-6862
57. Lee, S.; Hynes, J. T. Solution Phase Reaction Path Hamiltonian. II. Applications J. Chem. Phys. 1988, 88, 6863-6870
58. N2 Reaction in Water J. Chem. Phys. 1987, 86, 1356-1376
59. N2 Reactions in Polar Solvents J. Chem. Phys. 1987, 86, 1377-1386
60. N1 Ionic Dissociations in Solution. III. Analysis of t-Butyl Halide J. Am. Chem. Soc. 1993, 115, 8248-8262
61. An extensive list of theoretical and computational studies using a large electronic coupling (∼1 eV) for H-bond systems is given in Kiefer, P. M.; Hynes, J. T. Theoretical Aspects of Tunneling Proton Transfer Reactions in a Polar Environment J. Phys. Org. Chem. 2010, 23, 632-646
62. Kiefer, P. M.; Hynes, J. T. Kinetic Isotope Effects for Adiabatic Proton Transfer Reactions in a Polar Environment J. Phys. Chem. A 2003, 107, 9022-9039
63. The following ref and refs 67-69 are examples of the equilibrium solvation picture for PT in a complex system: Bash, P. A.; Field, M. J.; Davenport, R. C.; Petsko, G. A.; Ringe, D.; Karplus, M. Computer Simulation and Analysis of the Reaction Pathway of Triosephosphate Isomerase Biochemistry 1991, 30, 5826-5832
64. Cui, Q.; Karplus, M. Triosephosphate Isomerase: A Theoretical Comparison of Alternative Pathways J. Am. Chem. Soc. 2001, 123, 2284-2290
65. Alhambra, C.; Corchado, J.; Sánchez, M. L.; Garcia-Viloca, M.; Gao, J.; Truhlar, D. G. Canonical Variational Theory for Enzyme Kinetics with the Protein Mean Force and Multidimensional Quantum Mechanical Tunneling Dynamics. Theory and Application to Liver Alcohol Dehydrogenase J. Phys. Chem. B 2001, 105, 11326-11340
66. Cui, Q.; Elstner, M.; Karplus, M. A Theoretical Analysis of the Proton and Hydride Transfer in Liver Alcohol Dehydrogenase (LADH) J. Phys. Chem. B 2002, 106, 2721-2740
67. Marcus, R. A. Electrostatic Free Energy and Other Properties of States Having Nonequilibrium Polarization. I J. Chem. Phys. 1956, 24, 979-989
68. Marcus, R. A. Free Energy of Nonequilibrium Polarization Systems. II. Homogeneous and Electrode Systems J. Chem. Phys. 1963, 38, 1858-1862
69. Marcus, R. A. Free Energy of Nonequilibrium Polarization Systems. III. Statistical Mechanics of Homogeneous and Electrode Systems J. Chem. Phys. 1963, 39, 1734-1740
70. Kiefer, P. M.; Hynes, J. T. Kinetic Isotope Effects for Nonadiabatic Proton Transfer Reactions in a Polar Environment I. Interpretation of Tunneling Kinetic Isotope Effects J. Phys. Chem. A 2004, 108, 11793-11808
71. Kiefer, P. M.; Hynes, J. T. Kinetic Isotope Effects for Nonadiabatic Proton Transfer Reactions in a Polar Environment II. Comparison with an Electronically Diabatic Perspective J. Phys. Chem. A 2004, 108, 11809-11818
72. Ando, K.; Hynes, J. T. HF Acid Ionization in Water: The First Step Faraday Soc. Discuss. 1995, 102, 435-441
73. Ando, K.; Hynes, J. T. Molecular Mechanism of HCl Acid Ionization in Water. Ab Initio Potential Energy Surfaces and Monte Carlo Simulations J. Phys. Chem. B 1997, 101, 10464-10478
74. Gertner, B. J.; Hynes, J. T. Model Molecular Dynamics Simulation of Hydrochloric Acid Ionization at the Surface of Stratospheric Ice Faraday Soc. Discuss. 1998, 110, 301-322
75. Woutersen, S.; Bakker, H. J. Hydrogen Bond in Liquid Water as a Brownian Oscillator Phys. Rev. Lett. 1999, 83, 2077-2080
76. 2O) J. Chem. Phys. 2004, 120, 8345-8348
77. For a discussion of the Hellman-Feynman theorem, see chapter 14 in Levine, I. N. Quantum Chemistry, 4 th ed., Prentice Hall: Upper Saddle River, NJ, 1991.
78. Sheppard, N. Infrared Spectroscopy and Hydrogen Bonding - Band Widths and Frequency and Frequency Shifts. In Hydrogen Bonding, Hadzi, D., Ed.; Pergamon Press, Ltd.: London, 1959; pp 85-106.
79. Staib, A.; Hynes, J. T. Vibrational Predissociation in Hydrogen-Bonded OH⋯O Complexes via OH Stretch - OO Stretch Energy Transfer Chem. Phys. Lett. 1993, 204, 197-203
80. Klippenstein, S. K.; Hynes, J. T. Direct and Indirect Solvent Coupling Mechanisms for Vibrational Dephasing in Hydrogen-Bonded Molecules J. Phys. Chem. 1991, 95, 4651-4659
81. The basic form of eq 38 or 39 is reminiscent of the first order vibrational Stark (cf. Hush, N. S.; Reimers, J. R. Vibrational Stark Spectroscopy. 1. Basic Theory and Application to the CO Stretch J. Phys. Chem. 1995, 99, 15798-15805 and refs 88 and 89), where the absorption energy change is the difference in the dipole moment for the two states times the change in external field. This is made more explicit in the differential form d h ν = - (〈μ〉 eq 1 - 〈μ〉 eq 0) d R eq 0, relating the frequency change to the change in the solvent's equilibrium orientational polarization reaction field in the ground vibrational state (see the discussion above eq 11 for the sense of "equilibrium" here). While this connection provides some physical perspective for eqs 38 and 39, there are strong differences. Specifically, the orientational polarization's reaction field is not an independent external field, and there is an additional frequency-shifting solvent electronic polarization field effect on the ground and excited vibrational state wavefunctions
82. Hochstrasser, R. M. Electric Field Effects on Orientated Molecules and Molecular Crystals Acc. Chem. Res. 1973, 6, 263-269
83. Bublitz, G. U.; Boxer, S. G. Stark Spectroscopy: Applications in Chemistry, Biology, and Materials Science Annu. Rev. Phys. Chem. 1997, 48, 213-242
84. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
85. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
86. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-Consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72, 650-654
87. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094
88. 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. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
89. Mulliken, R. S. Molecular Compounds and their Spectra. III. The Interaction of Electron Donors and Acceptors J. Phys. Chem. 1952, 56, 801-822
90. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley: New York, 1969.
91. Ratajczak, H. Charge-Transfer Properties of the Hydrogen Bond. I. Theory of the Enhancement of Dipole Moment of Hydrogen-Bonded Systems J. Phys. Chem. 1972, 76, 3000-3004
92. Kiefer, P. M.; Leite, V. B. P.; Whitnell, R. M. A Simple Model for Proton Transfer Chem. Phys. 1995, 94, 33-44
93. NIST Chemistry WebBook. http://webbook.nist.gov/
94. Taft, R. W.; Topsom, R. D. The Nature and Analysis of Substitutent Electronic Effects Prog. Phys. Org. Chem. 1987, 16, 1-83 and refs 65-67
95. Hunter, E. P. L.; Lias, S. G. Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update J. Phys. Chem. Ref. Data 1998, 27, 413-656
96. Bartmess, J. E.; Scott, J. A.; McIver, R. T., Jr. Scale of Acidities in the Gas Phase from Methanol to Phenol J. Am. Chem. Soc. 1979, 101, 6046-6056
97. Fujio, M.; McIver, R. T., Jr.; Taft, R. W. Effects on the Acidities of Phenols from Specific Substituent-Solvent Interactions. Inherent Substituent Parameters from Gas-Phase Acidities J. Am. Chem. Soc. 1981, 103, 4017-4029
98. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
99. 2O)(n), (n = 0-3 and 5) clusters by infrared-ultraviolet double-resonance spectroscopy J. Chem. Phys. 1998, 109, 6303-63011
100. 3) Hydrogen-Bonded Clusters Investigated by IR-UV Double-Resonance Spectroscopy J. Mol. Struct. 2000, 552, 257-271
101. 3OH) clusters J. Phys. Chem. A 2001, 105, 5727-5730
102. Kouyama, K.; Miyazaki, M.; Mikami, N.; Ebata, T. IR laser Manipulation of cis↔trans Isomerization of 2-naphthol and its Hydrogen-Bonded Clusters J. Chem. Phys. 2006, 124, 054315
103. Schrems, O.; Oberhoffer, H. M.; Luck, W. A. P. Infrared Studies of Fluoroalcohol-Base Complexes in the Gas Phase, Carbon Tetrachloride Solutions, and Argon Matrices J. Mol. Struct. 1982, 80, 129-134
104. Hu, Y. J.; Fu, H. B.; Bernstein, E. R. Infrared Plus Vacuum Ultraviolet Spectroscopy of Neutral and Ionic Ethanol Monomers and Clusters J. Chem. Phys. 2006, 125, 154305
105. 3 in the S1 State J. Phys. Chem. A 1996, 100, 546-550
106. Iwasaki, A.; Fujii, A.; Watanabe, T.; Ebata, T.; Mikami, N. Infrared Spectroscopy of Hydrogen-Bonded Phenol-Amine Clusters in Supersonic Jets J. Phys. Chem. A 1996, 100, 16053-16057
107. Yamada, Y.; Ebata, T.; Kayano, M.; Mikami, N. Picosecond IR-UV pump-probe spectroscopic study of the dynamics of the vibrational relaxation of jet-cooled phenol. I. Intramolecular vibrational energy redistribution of the OH and CH stretching vibrations of bare phenol J. Chem. Phys. 2004, 120, 7400-7410
108. Kayano, M.; Ebata, T.; Yamada, Y.; Mikami, N. Picosecond IR-UV pump-probe spectroscopic study of the dynamics of the vibrational relaxation of jet-cooled phenol. II. Intracluster vibrational energy redistribution of the OH stretching vibration of hydrogen-bonded clusters J. Chem. Phys. 2004, 120, 7410-7418
109. Doi, A.; Mikami, N. Dynamics of hydrogen-bonded OH stretches as revealed by single-mode infrared-ultraviolet laser double resonance spectroscopy on supersonically cooled clusters of phenol J. Chem. Phys. 2008, 129, 154308
110. + properties, see Pople, J. A.; Curtiss, L. A. Theoretical Thermochemistry. 2. Ionization Energies and Proton Affinities of AHn Species (A = C to F and Si to Cl); Heats of Formation of their Cations J. Phys. Chem. 1987, 91, 155-162 and ref 124
111. Roszak, S. An Ab Initio Configuration Interaction Study of Deprotonation and Dehydrogenation Pathways of the Hydronium Cation Chem. Phys. Lett. 1996, 250, 187-191
112. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; 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
113. Light, J. C.; Hamilton, I. P.; Lill, J. V. Generalized Discrete Variable Approximation in Quantum Mechanics J. Chem. Phys. 1985, 82, 1400-1409
114. Choi, S. E.; Light, J. C. Determination of the Bound and Quasibound States of Ar-HCl van der Waals Complex: Discrete Variable Representation Method J. Chem. Phys. 1990, 92, 2129-2143
115. Bashford, D.; Case, D. A. Generalized Born Models of Macromolecular Solvation Effects Annu. Rev. Phys. Chem. 2000, 51, 129-152
116. Pines, E.; Pines, D. Proton Dissociation and Solute-Solvent Interactions Following Electronic Excitation and Photoacids. In Ultrafast Hydrogen Bonding Dynamics and Proton Transfer Processes in the Condensed Phase; Bakker, H.; Elsaesser, T., Eds.; Kluwer Academic Publishers: Boston, 2003; pp 155-184.
117. Nibbering, E. T. J.; Fidder, H.; Pines, E. Ultrafast Chemistry: Using Time-Resolved Vibrational Spectroscopy for Interrogation of Structural Dynamics Annu. Rev. Phys. Chem. 2005, 56, 337-367
118. Tolbert, L. M.; Solntsev, K. M. Excited-State Proton Transfer: From Constrained Systems to "Super" Photoacids to Superfast Proton Transfer Acc. Chem. Res. 2002, 35, 19-27
119. Pines, E.; Huppert, D. pH Jump: a Relaxational Approach J. Phys. Chem. 1983, 87, 4471-4478
120. Viappiani, C.; Bonetti, G.; Carcelli, M.; Ferrari, F.; Sternieri, A. Study of Proton Transfer Processes in Solution Using the Laser Induced pH -Jump: A New Experimental Setup and an Improved Data Analysis Based on Genetic Algorithms Rev. Sci. Instrum. 1998, 69, 270-276
121. Zelent, B.; Vanderkooi, J. M.; Coleman, R. G.; Gryczynski, I.; Gryczynski, Z. Protonation of Excited State Pyrene-1-Carboxylate by Phosphate and Organic Acids in Aqueous Solution Studied by Fluorescence Spectroscopy Biophys. J. 2006, 91, 3864-3871
122. Pines, E.; Huppert, D.; Gutman, M.; Nachliel, E.; Fishman, M. The p OH Jump: Determination of Deprotonation Rates of Water by 6-Methoxyquinoline and Acridine J. Phys. Chem. 1986, 90, 6366-6370
123. Hynes, J. T.; Tran-Thi, T.-H.; Granucci, G. Intermolecular Photochemical Proton Transfer in Solution: New Insights and Perspectives J. Photochem. Photobiol., A 2002, 154, 3-11
124. Granucci, G.; Hynes, J. T.; Millíe, P.; Tran-Thi, T.-H. A Theoretical Investigation of Excited State Acidity of Phenol and Cyanophenols J. Am. Chem. Soc. 2000, 122, 12235-12245