Chapter 2 Proton transfer in models of biomolecules

Theoretical and Computational Chemistry

Volumn 8, Issue C, 1999, Pages 35-83

  Scheiner, Steve ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 6344289214     PISSN: 13807323     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1380-7323(99)80077-6     Document Type: Chapter

References (162)

1. Pullman B., and Maigret B. In: Bergmann E.D., and Pullman B. (Eds). Conformation of Biological Molecules and Polymers (1973), Jerusalem Academic Press, Jerusalem 13
2. Scheiner S., and Kern C.W. Theoretical studies of environmental effects of protein conformation: Flexibility of the peptide bond. J. Am. Chem. Soc. 99 (1977) 7042
3. Wilson D.K., Rudolph F.B., and Quiocho F.A. Atomic structure of adenosine deaminase complexes with a transition-state analog: Understanding catalysis and immunodeficiency mutations. Science 252 (1991) 1278
4. Daggett V., Schröder S., and Kollman P. Catalytic pathway of serine proteases: Classical and quantum mechanical calculations. J. Am. Chem. Soc. 113 (1991) 8926
5. Bahnson B.J., Colby T.D., Chin J.K., Goldstein B.M., and Klinman J.P. A link between protein structure and enzyme catalyzed hydrogen tunneling. Proc. Nat. Acad. Sci., USA 94 (1997) 12797
6. Qian M., Tu C., Earnhardt J.N., Laipis P.J., and Silverman D.N. Glutamate and aspartate as proton shuttles in mutants of carbonic anhydrase. Biochem. 36 (1997) 15758
7. Kirby A.J. Efficiency of proton transfer catalysis in models and enzymes. Acc. Chem. Res. 30 (1997) 290
8. Richard J.P. The enhancement of enzymatic rate accelerations by Brønsted acid-base catalysis. Biochem. 37 (1998) 4305
9. Tu C., Qian M., Earnhardt J.N., Laipis P.J., and Silverman D.N. Properties of intramolecular proton transfer in carbonic anhydrase III. Biophys. J. 74 (1998) 3182
10. Saadat D., and Harrison D.H.T. Identification of catalytic bases in the active site of Escherichia coli methylglyoxal synthase: Cloning, expression, and functional characterization of conserved aspartic acid residues. Biochem. 37 (1998) 10074
11. 4 Cl reaction. J. Chem. Phys. 46 (1967) 3851
12. Baker E.N., and Hubbard R.E. Hydrogen bonding in globular proteins. Prog. Biophys. Molec. Biol. 44 (1984) 97
13. González L., Mó O., and Yáñez M. Proton transfer in dissociative protonation processes. J. Phys. Chem. A 102 (1998) 1356
14. - : A density functional and ab initio study. J. Mol. Struct. (Theochem) 427 (1998) 39
15. + . J. Chem. Phys. 101 (1994) 4878
16. - . J. Chem. Phys. 77 (1982) 4586
17. Hillenbrand E.A., and Scheiner S. Effects of molecular charge and methyl substitution on proton transfers between oxygen atoms. J. Am. Chem. Soc. 106 (1984) 6266
18. Wolfe S., Hoz S., Kim C.-K., and Yang K. Barrier widths, barrier heights, and the origins of anomalous kinetic H/D isotope effects. J. Am. Chem. Soc. 112 (1990) 4186
19. Kumar G.A., and McAllister M.A. Characterization of low-barrier hydrogen bonds. 8. Substituent effects on the strength and geometry of the formic acid-formate anion model system. An ab initio and DFT investigation. J. Am. Chem. Soc. 120 (1998) 3159
20. - anion: Its chemical bond, vibrations, and free energy. J. Chem. Phys. 91 (1989) 3539
21. Cybulski S., and Scheiner S. Hydrogen bonding and proton transfers involving triply bonded atoms. HC≡N and HC≡CH. J. Am. Chem. Soc. 109 (1987) 4199
22. Pan Y., and McAllister M.A. Characterization of low-barrier hydrogen bonds 4. Basis set and correlation effects: An ab initio and DFT investigation. J. Mol. Struct. (Theochem) 427 (1998) 221
23. 2 , and ClH. J. Phys. Chem. 89 (1985) 3669
24. Scheiner S., and Wang L. Effect of bond multiplicity upon hydrogen bonding and proton transfers. Double bonded atoms. J. Am. Chem. Soc. 114 (1992) 3650
25. - . Int. J. Quantum Chem. 29 (1986) 285
26. + . J. Chem. Phys. 82 (1985) 3316
27. Gronert S. Theoretical studies of proton transfers. 1. The potential energy surfaces of the identity reactions of the first-and second-row non-metal hydrides with their conjugate bases. J. Am. Chem. Soc. 115 (1993) 10258
28. + . J. Phys. Chem. 99 (1995) 1151
29. Kossiakoff A.A., Shpungin J., and Sintchak M.D. Hydroxyl hydrogen conformations in trypsin determined by the neutron diffraction solvent difference map method: Relative importance of steric and electrostatic factors in defining hydrogen-bonding geometries. Proc. Nat. Acad. Sci., USA 87 (1990) 4468
30. Ippolito J.A., Alexander R.S., and Christianson D.W. Hydrogen bond stereochemistry in protein structure and function. J. Mol. Biol. 215 (1990) 457
31. Scheiner S. Theoretical studies of proton transfers. Acc. Chem. Res. 18 (1985) 174
32. Janoschek R., Weidemann E.G., Pfeiffer H., and Zundel G. Extremely high polarizability of hydrogen bonds. J. Am. Chem. Soc. 94 (1972) 2387
33. Scheiner S. Proton transfers in hydrogen bonded systems. Cationic oligomers of water. J. Am. Chem. Soc. 103 (1981) 315
34. + and larger hydrated proton complexes. Int. J. Quantum Chem., Quantum Chem. Symp. 29 (1995) 657
35. 2 . J. Phys. Chem. 86 (1982) 376
36. + . J. Mol. Struct. (Theochem) 283 (1993) 57
37. + . J. Am. Chem. Soc. 94 (1972) 8301
38. Scheiner S., and Redfern P. Quantum mechanical test of Marcus theory. Effects of alkylation upon proton transfer. J. Phys. Chem. 90 (1986) 2969
39. Scheiner S., and Hillenbrand E.A. Comparison between proton transfers involving carbonyl and hydroxyl oxygens. J. Phys. Chem. 89 (1985) 3053
40. Hillenbrand E.A., and Scheiner S. Analysis of the principles governing proton transfer reactions. Comparison of the imine and amine groups. J. Am. Chem. Soc. 107 (1985) 7690
41. Cybulski S.M., and Scheiner S. Hydrogen bonding and proton transfers involving the carboxylate group. J. Am. Chem. Soc. 111 (1989) 23
42. + . Chem. Phys. Lett. 221 (1994) 523
43. Scheiner S., and Wang L. Hydrogen bonding and proton transfers of the amide group. J. Am. Chem. Soc. 115 (1993) 1958
44. Scheiner S., and Yi M. The proton transfer properties of imidazole. J. Phys. Chem. 100 (1996) 9235
45. Scheiner S., and Kar T. Proton and lithium ion transfer between two water molecules with an external restraining force. J. Am. Chem. Soc. 117 (1995) 1344
46. 2 . J. Chem. Phys. 77 (1982) 4039
47. + . J. Phys. Chem. 87 (1983) 1145
48. Redfern P., and Scheiner S. Effects of alkylation upon the proton affinities of nitrogen and oxygen bases. J. Comput. Chem. 6 (1985) 168
49. Marcus R.A. Chemical and electrochemical electron-transfer theory. Annu. Rev. Phys. Chem. 15 (1964) 155
50. Marcus R.A. Theoretical relation among rate constants, barriers, and Brønsted slopes of chemical reactions. J. Phys. Chem. 72 (1968) 891
51. Cohen A.O., and Marcus R.A. On the slope of free energy plots in chemical kinetics. J. Phys. Chem. 72 (1968) 4249
52. Albery W.J. The application of the Marcus relation to reactions in solution. Annu. Rev. Phys. Chem. 31 (1980) 227
53. Kresge A.J. What makes proton transfer fast?. Acc. Chem. Res. 8 (1975) 354
54. Scheiner S., and Duan X. Applicability of the Marcus equation to proton transfer in symmetric and unsymmetric systems. J. Mol. Struct. (Theochem) 285 (1993) 27
55. Murdoch J.R. Rate-equilibria relationships and proton-transfer reactions. J. Am. Chem. Soc. 94 (1972) 4410
56. Cao H.Z., Allavena M., Tapia O., and Evleth E.M. Model calculation of the intrinsic barrier for proton transfer in a carbon acid. Chem. Phys. Lett. 96 (1983) 458
57. Cao H.Z., Allavena M., Tapia O., and Evleth E.M. Theoretical analysis of proton transfers in symmetric and asymmetric systems. J. Phys. Chem. 89 (1985) 1581
58. Kristjánsdóttir S.S., and Norton J.R. Agreement of proton transfer cross reaction rates between transition metals with those predicted by Marcus theory. J. Am. Chem. Soc. 113 (1991) 4366
59. 2 SO-10% water. Determination of intrinsic barriers of identity reactions from the Marcus relationship. J. Am. Chem. Soc. 115 (1993) 5060
60. Duan X., and Scheiner S. Energetics, proton transfer rates, and kinetic isotope effects in bent hydrogen bonds. J. Am. Chem. Soc. 114 (1992) 5849
61. 2 , NH, and O. J. Comput. Chem. 7 (1986) 464
62. Wang X.-C., Nichols J., Feyereisen M., Gutowski M., Boatz J., Haymet A.D.J., and Simons J. Ab initio quantum chemistry study of formamide-formamidic acid tautomerization. J. Phys. Chem. 95 (1991) 10419
63. Bell R.L., and Truong T.N. Direct ab initio dynamics studies of proton transfer in hydrogen-bond systems. J. Chem. Phys. 101 (1994) 10442
64. Ikuta S., and Nomura O. Intramolecular hydrogen bonding of protonated ethylene diamine. J. Mol. Struct. (Theochem) 152 (1987) 315
65. Yates B.F., and Radom L. Intramolecular hydrogen migration in ionized amines: A theoretical study of the gas-phase analogues of the Hofmann-Löffler and related rearrangements. J. Am. Chem. Soc. 109 (1987) 2910
66. Fernández-Ramos A., Rodríguez-Otero J., and Ríos M.A. Intramolecular proton transfer direct dynamics in the glycolate anion: Isotope effects. J. Chem. Phys. 107 (1997) 2407
67. Truong T.N., and McCammon J.A. Direct dynamics study of intramolecular proton transfer in hydrogenoxalate anion. J. Am. Chem. Soc. 113 (1991) 7504
68. Fernández-Ramos A., Rodríguez-Otero J., and Ríos M.A. High level and dual level direct dynamics in the intramolecular proton transfer of hydrogenoxalate anion. Influence of tunneling and isotopic effect. J. Phys. Chem. A 102 (1998) 2954
69. Bosch E., Moreno M., Lluch J.M., and Bertrán J. Comparison between intramolecular proton transfers involving the carboxylate and alkoxide groups. Chem. Phys. 148 (1990) 77
70. Bosch E., Moreno M., and Lluch J.M. Intramolecular hydrogen bonding in ribonucleoside sugar hydroxyls. An ab initio study. Can. J. Chem. 70 (1992) 1640
71. Frisch M.J., Scheiner A.C., Schaefer H.F., and Binkley J.S. The malonaldehyde equilibrium geometry: A major structural shift due to the effects of electron correlation. J. Chem. Phys. 82 (1985) 4194
72. Karlström G., Jönsson B., Roos B., and Wennerström H. Correlation effects on barriers to proton transfer in intramolecular hydrogen bonds. The enol tautomer of malondialdehyde studied by ab initio SCF-CI calculations. J. Am. Chem. Soc. 98 (1976) 6851
73. Redington R.L., and Bock C.W. MO study of singlets, triplets, and tunneling in tropolone. 1. Geometries, tunneling, and vibrations in the ground electronic state. J. Phys. Chem. 95 (1991) 10284
74. George P., Bock C.W., and Trachtman M. An ab initio study of the planar hydrogen maleate ion with full geometry optimization. J. Phys. Chem. 87 (1983) 1839
75. Rios M.A., and Rodríguez J. Ab initio study of the structure of the hydrogen maleate anion. Can. J. Chem. 71 (1993) 303
76. Scheiner S. Bent hydrogen bonds and proton transfer. Acc. Chem. Res. 27 (1994) 402
77. Ceccarelli C., Jeffrey G.A., and Taylor R. A survey of O-H...O hydrogen bond geometries determined by neutron diffraction. J. Mol. Struct. 70 (1981) 255
78. Taylor R., Kennard O., and Versichel W. Geometry of the N-H...O=C hydrogen bond. 1. Lone-pair directionality. J. Am. Chem. Soc. 105 (1983) 5761
79. Taylor R., Kennard O., and Versichel W. Geometry of the N-H...O=C hydrogen bond. 2. Three-center ("bifurcated") and four-center ("trifurcated") bonds. J. Am. Chem. Soc. 106 (1984) 244
80. 3 -hybridized oxygen atoms and its relevance to ligand-macromolecule interactions. J. Am. Chem. Soc. 106 (1984) 1018
81. Hillenbrand E.A., and Scheiner S. Analysis of the principles governing proton-transfer reactions. Carboxyl group. J. Am. Chem. Soc. 108 (1986) 7178
82. Cybulski S.M., and Scheiner S. Factors contributing to distortion energies of bent hydrogen bonds. Implications for proton-transfer potentials. J. Phys. Chem. 93 (1989) 6565
83. + . J. Chem. Phys. 75 (1981) 5791
84. Eckert M., and Zundel G. Energy surfaces and proton polarizability of hydrogen-bonded chains: An ab inition treatment with respect to the charge conduction in biological systems. J. Phys. Chem. 92 (1988) 7016
85. Zundel G. Proton polarizability and proton transfer processes in hydrogen bonds and cation polarizabilities of other cation bonds-their importance to understand molecular processes in electrochemistry and biology. Trends Phys. Chem. 3 (1992) 129
86. Brzezinski B., Radziejewski P., Olejnik J., and Zundel G. An intramolecular hydrogen-bonded system with large proton polarizability-A model with regard to the proton pathway in bacteriorhodopsin and other systems with collective proton motion. J. Mol. Struct. 323 (1994) 71
87. + motions and cation polarizabilities of the cation-bonded systems within 1,11,12,13,14-pentahydroxypentacene salts: A FTIR study. J. Phys. Chem. 98 (1994) 2271
88. - . Ab initio SCF calculations. Coll. Czech. Chem. Commun. 43 (1978) 1956
89. Rode B.M. The influence of metal ions on neighboring hydrogen bonds. Theor. Chim. Acta 56 (1980) 245
90. David C.W. Electric field assisted proton transfer in the water dimer. Chem. Phys. Lett. 78 (1981) 488
91. Rode B.M., and Sagarik K.P. The influence of small monovalent cations on neighbouring N...H-O hydrogen bonds. Chem. Phys. Lett. 88 (1982) 337
92. 2+ ). J. Phys. Chem. 87 (1983) 573
93. 2+ ). Theor. Chim. Acta 81 (1992) 303
94. Scheiner S., Redfern P., and Szczesniak M.M. Effects of external ions on the energetics of proton transfers across hydrogen bonds. J. Phys. Chem. 89 (1985) 262
95. Mavri J., Hodoscek M., and Hadzi D. Ab initio SCF and Møller-Plesset calculations on the hydrogen bond in hydrogen malonate: Effects of neighbor ions and polarizable medium. J. Mol. Struct. (Theochem) 209 (1990) 421
96. Hodoscek M., and Hadzi D. Ab-initio calculations on the retinal Schiff base-formic acid and allylimine-formic acid hydrogen bonds. Can. J. Chem. 63 (1985) 1528
97. + B A proton-transfer hydrogen bond as a function of an external electrical field: An ab initio. J. Phys. Chem. 91 (1987) 5170
98. Scheiner S., and Das T. Effects of external ions upon proton transfer reactions. H-bonded systems containing HCOOH. Int. J. Quantum Chem., QBS 15 (1988) 137
99. Kurnig I.J., and Scheiner S. Additivity of the effects of external ions and dipoles upon the energetics of proton transfer. Int. J. Quantum Chem., QBS 13 (1986) 71
100. Scheiner S., Wang R., and Wang L. Perturbations of proton transfer potentials caused by polar molecules. Int. J. Quantum Chem., QBS 16 (1989) 211
101. Dijkman J.P., Osman R., and Weinstein H. A theoretical study of the effect of primary and secondary structure elements on the proton transfer in papain. Int. J. Quantum Chem. 35 (1989) 241
102. Onsager L. Electric moments of molecules in liquids. J. Am. Chem. Soc. 58 (1936) 1486
103. Kirkwood J.G., and Westheimer F.H. The electrostatic influence of substituents on the dissociation constants of organic acids. I. J. Chem. Phys. 6 (1938) 506
104. Gilson M.K., and Honig B.H. The dielectric constant of a folded protein. Biopolymers 25 (1986) 2097
105. Tapia O., and Goscinski O. Self-consistent reaction field theory of solvent effects. Mol. Phys. 29 (1975) 1653
106. Sanhueza J.E., and Tapia O. The quantum chemical calculation of environmental effects: A comparative study of charge separation in water dimers. J. Mol. Struct. (Theochem) 89 (1982) 131
107. Olivares del Valle F.J., and Tomasi J. Electron correlation and solvation effects. I. Basic formulation and preliminary attempt to include the electron correlation in the quantum mechanical polarizable continuum model so as to study solvation phenomena. Chem. Phys. 150 (1991) 139
108. Wong M.W., Frisch M.J., and Wiberg K.B. Solvent effects. 1. The mediation of electrostatic effects by solvents. J. Am. Chem. Soc. 113 (1991) 4776
109. Kurnig I.J., and Scheiner S. Ab initio investigation of the structure of hydrogen halide-amine complexes in the gas phase and in a polarizable medium. Int. J. Quantum Chem., QBS 14 (1987) 47
110. Thole B.T., and van Duijnen P.T. Reaction field effects on proton transfer in the active site of actinidin. Biophys. Chem. 18 (1983) 53
111. Sapse A.M., and Russell C.S. Theoretical studies of the binding of methylamine and guanidine to carboxylate. J. Mol. Struct. (Theochem) 137 (1986) 43
112. Parra-Mouchet J., Contreras R.R., and Aizman A. Self-consistent reaction field calculations on the proton transfer in ammonia-formic acid systems as a model for hydrogen bonding in amino acids in solution. Int. J. Quantum Chem. 33 (1988) 41
113. Hadzi D., Koller J., and Hodoscek M. Ab initio calculations of proton potential functions of some rhodopsin modelling systems. J. Mol. Struct. (Theochem) 168 (1988) 279
114. Hodoscek M., Hadzi D., and Solmajer T. Ab initio MO calculations of hydrogen bonding between guanidine isosters and carboxylate. J. Mol. Struct. (Theochem) 183 (1989) 371
115. Karlström G. Proton transport in water modeled by a quantum chemical dielectric cavity model. J. Phys. Chem. 92 (1988) 1318
116. Dijkman J.P., and van Duijnen P.T. Papain in aqueous solution and the role of Asp-158 in the mechanism: An ab initio SCF+DRF+BEM study. Int. J. Quantum Chem., QBS 18 (1991) 49
117. Tortonda F.R., Pascual-Ahuir J.-L., Silla E., and Tuñón I. Proton transfer between water molecules. A theoretical study of solvent effects using the continuum and the discrete-continuum models. J. Phys. Chem. 97 (1993) 11087
118. Tuñón I., Tortonda F.R., Pascual-Ahuir J.-L., and Silla E. Correlation effects in proton transfer reactions in solution. J. Mol. Struct. (Theochem) 371 (1996) 117
119. Scheiner S., and Duan X. Effect of intermolecular orientation upon proton transfer within a polarizable medium. Biophys. J. 60 (1991) 874
120. Tomasi J., Bonaccorsi R., Cammi R., and Olivartes del Valle F.J. Theoretical chemistry in solution. Some results and perspectives of the continuum methods and in particular of the polarizable continuum model. J. Mol. Struct. (Theochem) 234 (1991) 401
121. Furuki T., Hosokawa F., Sakurai M., Inoue Y., and Chujo R. Microscopic medium effects on a chemical reaction. A theoretical study of decarboxylation catalyzed by cyclodextrins as an enzyme model. J. Am. Chem. Soc. 115 (1993) 2903
122. Cramer C.J., and Truhlar D.G. Polarization of the nucleic acid bases in aqueous solution. Chem. Phys. Lett. 198 (1992) 74
123. - anion. A very short, symmetric hydrogen bond. J. Am. Chem. Soc. 101 (1979) 3688
124. Joswig W., Fuess H., and Ferraris G. Neutron diffraction study of the hydrogen bond in trisodium hydrogenbissulphate and a survey of very short O-H...O bonds. Acta Cryst. B38 (1982) 2798
125. Alder R.W. Strain effects on amine basicities. Chem. Rev. 89 (1989) 1215
126. Hibbert F., and Emsley J. Hydrogen bonding and chemical reactivity. Adv. Phys. Org. Chem. 26 (1990) 255
127. Steiner T., and Saenger W. Lengthening of the covalent O-H bond in O-H...O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds. Acta Cryst. B50 (1994) 348
128. Gilli P., Bertolasi V., Ferretti V., and Gilli G. Covalent nature of the strong homonuclear hydrogen bond. Study of the O-H...O system by crystal structure correlation methods. J. Am. Chem. Soc. 116 (1994) 909
129. Goncharov A.F., Struzhkin V.V., Somayazulu M.S., Hemley R.J., and Mao H.K. Compression of ice to 210 gigapascals: Infrared evidence for a symmetric hydrogen-bonded phase. Science 273 (1996) 218
130. Cleland W.W. Low-barrier hydrogen bonds and low fractionation factor bases in enzymatic reactions. Biochem. 31 (1992) 317
131. Gerlt J.A., and Gassman P.g. Understanding the rates of certain enzyme-catalyzed reactions: Proton abstraction from carbon acids, acyl-transfer reactions, and displacement reactions of phosphodiesters. Biochem. 32 (1993) 11943
132. Gerlt J.A., and Gassman P.G. An explanation for rapid enzyme-catalyzed proton abstraction from carbon acids: Importance of late transition states in concerted mechanisms. J. Am. Chem. Soc. 115 (1993) 11552
133. Cleland W.W., and Kreevoy M.M. Low-barrier hydrogen bonds and enzymic catalysis. Science 264 (1994) 1887
134. 5 -3-ketosteroid isomerase. Proc. Nat. Acad. Sci., USA 93 (1996) 8220
135. Frey P.A., Whitt S.A., and Tobin J.B. A low-barrier hydrogen bond in the catalytic triad of serine proteases. Science 264 (1994) 1927
136. Tobin J.B., Whitt S.A., Cassidy C.S., and Frey P.A. Low-barrier hydrogen bonding in molecular complexes analogous to histidine and aspartate in the catalytic triad of serine proteases. Biochem. 34 (1995) 6919
137. Ash E.L., Sudmeier J.L., De Fabo E.C., and Bachovchin W.W. A low-barrier hydrogen bond in the catalytic triad of serine proteases? Theory versus experiment. Science 278 (1997) 1128
138. Garcia-Viloca M., Gelabert R., González-Lafont A., Moreno M., and Lluch J.M. Is an extremely low-field proton signal in the NMR spectrum conclusive evidence for a low-barrier hydrogen bond?. J. Phys. Chem. A 101 (1997) 8727
139. Usher K.C., Remington S.J., Martin D.P., and Drueckhammer D.G. A very short hydrogen bond provides only moderate stabilization of an enzyme-inhibitor complex of citrate synthase. Biochem. 33 (1994) 7753
140. Kato Y., Toledo L.M., and Rebek Jr. J. Energetics of a low barrier hydrogen bond in nonpolar solvents. J. Am. Chem. Soc. 118 (1996) 8575
141. Schwartz B., and Drueckhammer D.G. A simple method for determining the relative strengths of normal and low-barrier hydrogen bonds in solution: Implications to enzyme catalysis. J. Am. Chem. Soc. 117 (1995) 11902
142. Garcia-Viloca M., González-Lafont A., and Lluch J.M. Theoretical study of the low-barrier hydrogen bond in the hydrogen maleate anion in the gas phase. Comparison with normal hydrogen bonds. J. Am. Chem. Soc. 119 (1997) 1081
143. 15 N NMR and theoretical studies of primary and secondary geometric H/D isotope effects on low-barrier NHN-hydrogen bonds. J. Am. Chem. Soc. 120 (1998) 2939
144. Scheiner S., and Kar T. The nonexistence of specially stabilized hydrogen bonds in enzymes. J. Am. Chem. Soc. 117 (1995) 6970
145. Warshel A., Papazyan A., and Kollman P.A. On low-barrier hydrogen bonds and enzyme catalysis. Science 269 (1995) 102
146. Warshel A., and Papazyan A. Energy considerations show that low-barrier hydrogen bonds do not offer a catalytic advantage over ordinary hydrogen bonds. Proc. Nat. Acad. Sci., USA 93 (1996) 13665
147. a matching as a requirement to form a low-barrier hydrogen bond. A theoretical study in the gas phase. J. Phys. Chem. A 101 (1997) 3880
148. Pan Y., and McAllister M.A. Characterization of low-barrier hydrogen bonds. 1. Microsolvation effects. An ab initio and DFT investigation. J. Am. Chem. Soc. 119 (1997) 7561
149. McAllister M.A. Characterization of low-barrier hydrogen bonds. 3. hydrogen maleate. An ab initio and DFT investigation. Can. J. Chem. 75 (1997) 1195
150. Pan Y., and McAllister M.A. Characterization of low-barrier hydrogen bonds 6. Effects on the formic acid-formate anion model system. An ab initio and DFT investigation. J. Am. Chem. Soc. 120 (1998) 166
151. Smallwood C.J., and McAllister M.A. Characterization of low-barrier hydrogen bonds 7. Relationship between strength and geometry of short-strong hydrogen bonds. An ab initio and DFT investigation. J. Am. Chem. Soc. 119 (1997) 11277
152. Perrin C.L., and Nielson J.B. "Strong" hydrogen bonds in chemistry and biology. Annu. Rev. Phys. Chem. 48 (1997) 511
153. Scheiner S. Hydrogen Bonding. A Theoretical Perspective (1997), Oxford University Press, New York
154. Yamdagni R., and Kebarle P. Hydrogen-bonding energies to negative ions from gasphase measurements of ionic equilibria. J. Am. Chem. Soc. 93 (1971) 7139
155. Yamdagni R., and Kebarle P. Gas-phase basicities of amines. Hydrogen bonding in proton-bound amine dimers and proton-induced cyclization of α,ω-diamines. J. Am. Chem. Soc. 95 (1973) 3504
156. Caldwell G., Rozeboom M.D., Kiplinger J.P., and Bartmess J.E. Anion-alcohol hydrogen bond strengths in the gas phase. J. Am. Chem. Soc. 106 (1984) 4660
157. + ...O bonds. Correlations with proton affinity. Deviations due to structural effects. J. Am. Chem. Soc. 106 (1984) 1257
158. - bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions. J. Am. Chem. Soc. 108 (1986) 7525
159. Meot-Ner M. Models for strong interactions in proteins and enzymes. 2. Interactions of ions with the peptide link and with imidazole. J. Am. Chem. Soc. 110 (1988) 3075
160. Feng W.Y., Ling Y., and Lifshitz C. Reactivity of mixed and neat proton bound dimers of acetonitrile and methyl acetate. J. Phys. Chem. 100 (1996) 35
161. Shan S., Loh S., and Herschlag D. The energetics of hydrogen bonds in model systems: Implications for enzymatic catalysis. Science 272 (1996) 97
162. Shan S., and Herschlag D. The change in hydrogen bond strength accompanying charge rearrangement: Implications for enzymatic catalysis. Proc. Nat. Acad. Sci., USA 93 (1996) 14474