Fundamental thermochemical properties of amino acids: Gas-phase and aqueous acidities and gas-phase heats of formation

Journal of Physical Chemistry B

Volumn 116, Issue 9, 2012, Pages 2905-2916

  Stover, Michele L ^a   Jackson, Virgil E ^a   Matus, Myrna H ^a   Adams, Margaret A ^a   Cassady, Carolyn J ^a   Dixon, David A ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; FORECASTING;

ATOMIZATION ENERGIES; CALCULATED VALUES; ENERGY CONFORMERS; EXPERIMENTAL ERRORS; FREE-ENERGY DIFFERENCE; GAS-PHASE ACIDITIES; GASPHASE; HEATS OF FORMATION; ISODESMIC REACTIONS; L-AMINO ACIDS; NEUTRAL COMPOUNDS; PARAMETRIZATIONS; SELF-CONSISTENT REACTION FIELDS; THERMOCHEMICAL PROPERTIES;

AMINO ACIDS;

EID: 84858021409     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp207271p     Document Type: Article

References (91)

1. Ewing, N. P.; Cassady, C. J. J. Am. Soc. Mass Spectrom. 2001, 12, 105-116
2. Jai-nhuknan, J.; Cassady, C. J. Anal. Chem. 1998, 70, 5122-5128
3. Brinkworth, C. S.; Dua, S.; Bowie, J. H. Eur. J. Mass Spectrom. 2002, 8, 53-66
4. MacLean, M. J.; Brinkworth, C. S.; Bilusich, D.; Bowie, J. H.; Doyle, J. R.; Llewellyn, L. E.; Tyler, M. Toxicon Mass Spectrometry in Toxinology-A 21st-Century Technology for the Study of Biopolymers from Venoms 2006, 47, 664-675
5. Marzluff, E. M.; Campbell, S.; Rodgers, M. T.; Beauchamp, J. L. J. Am. Chem. Soc. 1994, 116, 7787-7796
6. Harrison, A. G. J. Am. Soc. Mass Spectrom. 2001, 12, 1-13
7. Bowie, J. H.; Brinkworth, C. S.; Dua, S. Mass Spectrom. Rev. 2002, 21, 87-107
8. Bilusich, D.; Bowie, J. H. Mass Spectrom. Rev. 2009, 28, 20-34
9. McLuckey, S. A.; Cameron, D.; Cooks, R. G. J. Am. Chem. Soc. 1981, 103, 1313-1317
10. Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F. Mass Spectrom. Rev. 1990, 9, 37-70
11. Hillenkamp, F.; Karas, M.; Beavis, R. C.; Chait, B. T. Anal. Chem. 1991, 63, 1193A-1203A
12. Wysocki, V. H.; Tsaprailis, G.; Smith, L. L.; Breci, L. A. J. Mass Spectrom. 2000, 35, 1399-1406
13. Cox, K. A.; Gaskell, S. J.; Morris, M.; Whiting, A. J. Am. Soc. Mass Spectrom. 1996, 7, 522-531
14. Johnson, R. S.; Martin, S. A.; Biemann, K. Int. J. Mass Spectrom. Ion Proc. 1988, 86, 137-154
15. Ghelis, C.; Yon, J. Protein Folding; Academic Press: New York, 1982.
16. McCammon, J. A.; Harvey, S. C. Dynamics of Proteins and Nucleic Acids; Cambridge University Press: Cambridge, 1987.
17. Margoulies, M.; Greenwood, F. C. Structure-Activity Relationships of Protein and Polypeptide Hormones; Excerpta Medica Foundation: Amsterdam, 1972.
18. Cassady, C. J.; Carr, S. R.; Zhang, K.; Chung-Phillips, A. J. Org. Chem. 1995, 60, 1704-1712
19. Carr, S. R.; Cassady, C. J. J. Am. Soc. Mass Spectrom. 1996, 7, 1203-1210
20. Wu, J.; Lebrilla, C. B. J. Am. Chem. Soc. 1993, 115, 3270-3275
21. Gorman, G. S.; Speir, J. P.; Turner, C. A.; Amster, I. J. J. Am. Chem. Soc. 1992, 114, 3986-3988
22. Wu, Z.; Fenselau, C. Rapid Commun. Mass Spectrom. 1992, 6, 403-405
23. Sun, W.; Kinsel, G. R.; Marynick, D. S. J. Phys. Chem. A 1999, 103, 4113-4117
24. Noguera, M.; Rodriguez-Santiago, L.; Sodupe, M.; Bertran, J. J. Mol. Struct. THEOCHEM 2001, 537, 307-318
25. Dinadayalane, T. C.; Sastry, G. N.; Leszczynski, J. Int. J. Quantum Chem. 2006, 106, 2920-2933
26. Bleiholder, C.; Shuai, S.; Paizs, B. J. Am. Soc. Mass Spectrom. 2006, 17, 1275-1281
27. Harrison, A. G. Mass Spectrom. Rev. 1997, 16, 201-217
28. Gronert, S.; Simpson, D. C.; Conner, K. M. J. Am. Soc. Mass Spectrom. 2009, 20, 2116-2123
29. Locke, M. J.; McIver, R. T., Jr. J. Am. Chem. Soc. 1983, 105, 4226-4232
30. Meot-Ner, M.; Hunter, E. P.; Field, F. H. J. Am. Chem. Soc. 1979, 101, 686-689
31. Tian, Z.; Poutsma, J. C.; Pawlow, A.; Kass, S. R. J. Am. Chem. Soc. 2007, 129, 5403-5407
32. Woo, H. K.; Lau, K. C.; Wang, X. B.; Wang, L. S. J. Phys. Chem. A 2006, 110, 12603-12606
33. Caldwell, G.; Renneboog, R.; Kebarle, P. Can. J. Chem. 1989, 67, 611-618
34. O'Hair, R. A. J.; Bowie, J. H.; Gronert, S. Int. J. Mass Spectrom. Ion Proc. 1992, 117, 23-36
35. Li, Z.; Velazquez, H. A.; Hernandez-Matus, M.; Dixon, D. A.; Cassady, C. J. Int. J. Mass Spectrom. 2007, 265, 213-223
36. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703-4709
37. Gutowski, K. E.; Dixon, D. A. J. Phys. Chem. A 2006, 110, 12044-12054
38. Fournier, F.; Afonso, Cl; Fagin, A. E.; Gronert, S.; Tabet, J-C J. Am. Soc. Mass. Spectrom 2008, 19, 1887-1897
39. Jones, C. M.; Bernier, M.; Carson, E.; Colyer, K. E.; Metz, R.; Pawlow, A.; Wischow, E. D.; Webb, I.; Andriole, E. J.; Poutsma, J. C. Int. J. Mass Spectrom. 2007, 267, 54-62
40. Miao, R.; Jin, C.; Yang, G.; Hong, J.; Zhao, C.; Zhu, L. J. Phys. Chem. A 2005, 109, 2340-2349
41. Tian, Z.; Wang, X.-B.; Wang, L.-S.; Kass, S. R. J. Am. Chem. Soc. 2009, 131, 1174-1181
42. Tian, Z.; Kass, S. R. J. Am. Chem. Soc. 2008, 130, 10842-10843
43. Oomens, J.; Steill, J. D.; Redlich, B. J. Am. Chem. Soc. 2009, 131, 4310-4319
44. Skurski, P.; Gutowski, M.; Barrios, R.; Simons, J. Chem. Phys. Lett. 2001, 337, 143-150
45. Rak, J.; Skurski, P.; Simons, J.; Gutowski, M. J. Am. Chem. Soc. 2001, 123, 11695-11707
46. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
47. Klamt, A.; Schüürmann, G. J. Chem. Soc. Perkin Trans. 1993, 2, 799-805
48. Lehninger, A. L. Biochemistry, 2 nd ed.; Worth Publishers Inc.: New York, 1970.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuna, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowshi, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
51. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
52. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571
53. Sun, W.; Kinsel, G. R.; Marynick, D. S. J. Phys. Chem. A 1999, 103, 4113-4117
54. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796-6806
55. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703-4709
56. Bartmess, J. E.; Linstrom, P. J.; Mallard, W. G., Eds.; Negative Ion Energetics Data; NIST Chemistry WebBook, NIST Standard Reference Database Number 69; National Institute of Standards and Technology: Gaithersburg MD, 2005; http://webbook.nist.gov.
57. Feller, D.; Dixon, D. A. J. Chem. Phys. 2001, 115, 3484-3496
58. Ruscic, B.; Wagner, A. F.; Harding, L. B.; Asher, R. L.; Feller, D.; Dixon, D. A.; Peterson, K. A.; Song, Y.; Qian, X.; Ng, C.; Liu, J.; Chen, W.; Schwenke, D. W. J. Phys. Chem. A 2002, 106, 2727-2747
59. Dixon, D. A.; Feller, D.; Peterson, K. A. J. Chem. Phys. 2001, 115, 2576-2581
60. Pollack, L.; Windus, T. L.; de Jong, W. A.; Dixon, D. A. J. Phys. Chem. A 2005, 109, 6934-6938
61. Feller, D.; Peterson, K. A.; Dixon, D. A. J. Chem. Phys. 2008, 129, 204015-204046
62. Purvis, G. D., III; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918
63. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479-483
64. Watts, J. D.; Gauss, J.; Bartlett, R. J. J. Chem. Phys. 1993, 98, 8718-8733
65. Bartlett, R. J.; Musial, M. Rev. Mod. Phys. 2007, 79, 291-352
66. Deegan, M. J. O.; Knowles, P. J. Chem. Phys. Lett. 1994, 227, 321-326
67. Knowles, P. J.; Hampel, C.; Werner, H.-J. J. Chem. Phys. 1993, 99, 5219-5227
68. Rittby, M.; Bartlett, R. J. J. Phys. Chem. 1988, 92, 3033-3036
69. Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 7410-7415
70. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1995, 103, 4572-4585
71. Peterson, K. A.; Dunning, T. H., Jr. J. Chem. Phys. 2002, 117, 10548-10560
72. Davidson, E. R.; Ishikawa, Y.; Malli, G. L. Chem. Phys. Lett. 1981, 84, 226-229
73. Moore, C. E. Atomic Energy Levels as Derived from the Analysis of Optical Spectra; Vol. 1, H to V; U.S. National Bureau of Standards Circular 467; U.S. Department of Commerce, National Technical Information Service: Washington, DC, 1949.
74. Chase, M. W., Jr. NIST-JANAF Thermochemical Tables, 4 th ed.; J. Phys. Chem. Ref. Data, Mono. 9; American Institute of Physics: Woodbury, NY, 1998; Suppl 1.
75. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063-1079
76. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 1999, 110, 7650-7657
77. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 2007, 126, 84108-84108•12
78. Lee, T. J.; Rice, J. E.; Scuseria, G. E.; Schaefer, H. F. Theor. Chim. Acta 1989, 75, 81-89
79. Lee, T. J.; Taylor, P. R. Int. J. Quantum Chem. Symp. 1989, 23, 199-207
80. Lee, T. J. Chem. Phys. Lett. 2003, 372, 362-367
81. Price, W. D.; Jockusch, R. A.; Williams, E. R. J. Am. Chem. Soc. 1997, 119, 11988-11989
82. Forbes, M. W.; Bush, M. F.; Polfer, N. C.; Oomens, J.; Dunbar, R. C.; Williams, E. R.; Jockusch, R. A. J. Phys. Chem. A 2007, 111, 11759-11770
83. Bush, M. F.; Prell, J. S.; Saykally, R. J.; Williams, E. R. J. Am. Chem. Soc. 2007, 129, 13544-13553
84. O'Brien, J. T.; Prell, J. S.; Berden, G.; Oomens, J.; Williams, E. R. Int. J. Mass Spec 2010, 297, 116-123
85. Mangold, M.; Rolland, L.; Costanzo, F.; Sprik, M.; Sulpizi, M.; Blumberger J. Chem. Theory Comput. 2011, 7, 1951-1961
86. Harris, D. C. Quantitative Chemical Analysis; W. H. Freeman: New York, 2007; Chapter 10, pp 180-183.
87. Ho, J. M.; Coote, M. L. J. Chem. Theory Comput. 2009, 5, 295-306
88. Ngauv, S. N.; Sabbah, R.; Laffitte, M. Thermochim. Acta 1977, 20, 371-380
89. Sabbah, R.; Laffitte, M. Bull. Soc. Chim. Fr. 1978, 1, 50-52
90. Sabbah, R.; Laffitte, M. Thermochim. Acta 1978, 23, 192-195
91. Sagadeev, E. V.; Gimadeev, A. A.; Barabanov, V. P. Russ. J. Phys. Chem. A 2010, 84, 209-214