Hydration of the Carbonyl Group. A Theoretical Study of the Cooperative Mechanism

Journal of the American Chemical Society

Volumn 117, Issue 15, 1995, Pages 4240-4260

  Wolfe, Saul ^a   Kim, Chan Kyung ^a,c   Yang, Kiyull ^b   Weinberg, Noham ^a   Shi, Zheng ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

^b Gyeongsang National University   (South Korea)

^c Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001710855     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00120a005     Document Type: Article

References (62)

1. Bell, R. P. Adv. Phys. Org. Chem. 1966, 4, 1–29.
2. Jencks, W. P. Catalysis in Chemistry and Enzymology; Dover Publications, Inc.: New York, 1987.
3. Zavitsas, A. A.; Coffiner, M.; Wiseman, T.; Zavitsas, L. R. J. Phys. Chem. 1970, 74, 2746-2750
4. 3dand application of the van't Hoff equation to the data of ref 3a.
5. Bell, R. P.; Evans, P. G. Proc. R. Soc. London, Ser. A. 1966, 291, 297-323
6. Valenta, P. Collect. Czech. Chem. Commun. 1960, 25, 853-861.
7. Bell, R. P.; Rand, M. H.; Wynne-Jones, K. M. A. Trans. Faraday Soc. 1956, 52, 1093–1102. Critchlow, J. E. J. Chem. Soc., Faraday Trans. 1 1972, 68, 1774–1992.
8. 4a
9. Pocker, Y. Proc. Chem. Soc. 1960, 17–18.
10. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 5444–5459. Sørensen. P. E.; Jencks, W. P. J. Am. Chem. Soc. 1987, 109, 4675–4690.
11. Eigen, M. Discuss. Faraday Soc. 1965, 39, 7-15.
12. Dahn, H.; Aubort, J.-D. Helv. Chim. Acta 1968, 51, 1348–1352. Haldna, U. L.; Erreline, L. E.-J.; Kuura, H. J. Org. React. (USSR) 1968, 5, 202; Sørensen, P. E. Acta Chem. Scand., Ser. A 1976, 30, 673-679.
13. Bell, R. P.; Millington, J. P.; Pink, J. M. Proc. R. Soc. London, Ser. A 1968, 303, 1-16. Bell, R. P.; Critchlow, J. E. Proc. R. Soc. London, Ser. A 1971, 325, 35-55. Bell, R. P.; Sörensen, P. E. J. Chem. Soc. Perkin Trans. 2, 1972, 1740–1743.
14. Grunwald, E.; Jumper, C. F.; Meiboom, S. J. Am. Chem. Soc. 1963, 85, 522–528. Grunwald, E.; Meiboom, S. J. Am. Chem. Soc. 1963, 85, 2047–2050. Luz., Z.; Meiboom, S. J. Am. Chem. Soc. 1963, 85, 3923.
15. β-Lactamases are divided into four classes (A, B, C, and D) on the basis of their structures and specificities. The class A are the most commonly encountered. See, e.g.: Ambler, R. P.; Coulson, A. F.; Frère, J.-M.; Ghuysen, J.-M.; Forsman, M.; Joris, B.; Levesque, R.; Tiraby, G.; Waley, S. G. Biochem. J. 1991, 276, 269–270. Joris, B.; Ledent, P.; Dideberg, O.; Fonzé, E.; Lamotte-Brasseur, J.; Kelly, J. A.; Ghuysen, J.-M.; Frère, J.-M. Antimicrob. Agents Chemother. 1991, 35, 2294-2301.
16. For the crystal structure of a β-lactamase from Staphylococcus aureus, see: Herzberg, O. J. Mol. Biol. 1991, 217, 701-719. For the β-lactamase from Bacillus licheniformis, see: Knox, J. R.; Moews, P. C. J. Mol. Biol. 1991, 220, 435–455. For the crystal structure of the RTEM-1 enzyme from Escherichia coli, see: Jelsch, C.; Lenfant, F.; Masson, J. M.; Samama, J. P. FEBS Lett. 1992, 299, 135–142. Strydnadka, N. C. J.; Adachi, H.; Jensen, S. E.; Johns, K.; Sielecki, A.; Betzel, C.; Sutoh, K.; James, M. N. G. Nature 1992, 359, 700–705.
17. Abraham, E. P.; Chain, E. Nature 1940, 146, 837. Kelly, J.; Dideberg, O.; Charlier, P.; Wéry, J.; Libert, M.; Moews, P.; Knox, J.; Duez C.; Fraipont, C.; Joris, B.; Dusart, D.; Frère, J.-M.; Ghuysen, J.-M. Science 1986, 231, 1429–1431. Abraham, E. P. BioEssays 1990, 12, 601-606 Abraham, E. P. J. Chemother. 1991, 3, 67-74.
18. Escobar, W. A.; Tan, A. K.; Fink, A. L. Biochemistry 1991, 30, 10783–10787.
19. Madura, J. M.; Jorgensen, W. L. J. Am. Chem. Soc. 1986, 108, 2517-2527. Ventura, O. N.; Coitiño, E. L.; Irving, K.; Iglesias, A. J. Mol. Struct. (Theochem) 1990, 210, 427-440. Peeters, D.; Leroy, G. Can. J. Chem. 1991, 69, 1376–1387. Tachibana, A.; Fueno, H.; Yamato, M.; Yamabe, T. Int. J. Quantum Chem. 1991, 40, 435-456. Ventura, O. N.; Apostolova, E. S. J. Org. Chem. USSR 1991, 27, 573-579. Coitiño, E. L.; Lledós, A.; Bertran, J. J. Comput. Chem. 1992, 13, 1037-1046. For related work, see: Kozmutza, C.; Ozoróczy, Zs.; Kapuy, E. J. Mol. Struct. (Theochem) 1990, 204, 101–109.
20. Venkatasubban, K. S.; Schowen, R. L. CRC Crit. Rev. Biochem. 1981, 17, 1–44.
21. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986.
22. Eisenberg, D.; Kauzmann, W. The Structure and Properties of Water; Clarendon Press: Oxford, 1969; Franks, F., Ed. Water, A Comprehensive Treatise; Plenum Press: New York; Vols. 1-7.
23. Dimer: Dyke, T. R.; Mack, K. M.; Muenter, J. S. J. Chem. Phys. 1977, 66, 498–510. Odutola, J. A.; Hu, T. A.; Prinslow, D.; O'Dell, S. E.; Dyke, T. R. J. Chem. Phys. 1988, 88, 5352-5361. Slanina, Z. Ber. Bunsenenges. Phys. Chem. 1993, 97, 558-561. Pugliano, N.; Saykally, R. J. J. Chem. Phys. 1992, 96, 1832–1839. Cyclic trimer: Pugliano, N.; Saykally, R. J. Science 1992, 257, 1937–1940. Saykally, R. J.; Blake, G. A. Science 1993, 259, 1570-1575. Cyclic tetramer and cubic octamer: Benson, S. W.; Siebert, E. D. J. Am. Chem. Soc. 1992, 114, 4269–4276. Bertagnolli, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1577–1578.
24. Dimer: Slanina, Z. Chem. Phys. 1991, 150, 321–329. Bertran, J.; Ruiz-López, M. F.; Rinaldi, D.; Rivail, J. L. Theor. Chim. Acta 1992, 84, 181–194. Millot, C.; Stone, A. J. Mol. Phys. 1992, 77, 439–462.
25. Cyclic trimer: Mó, O.; Yáñez, M.; Elguero, J. J. Chem. Phys. 1992, 97, 6628–6638. Vegiri, A.; Farantos, S. C. J. Chem. Phys. 1993, 98, 4059–4075. Xantheas, S. S.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 8037–8040. Wales, D. J. J. Am. Chem. Soc. 1993, 115, 11180–11190. van Duijneveldt-van de Rijdt, J. G. C. M.; van Duijneveldt, F. B. Chem. Phys. 1993, 175, 271-281.
26. Cyclic tetramer: Koehler, J. E. H.; Saenger, W.; Lesyng, B. J. Comput. Chem. 1987, 8, 1090-1098. Ferrari, A. M.; Garrone, E.; Ugliengo, P. Chem. Phys. Lett. 1993, 212, 644–648 and references cited therein.
27. Octamer: Corongiu, G.; Clementi, E. Chem. Phys. Lett. 1993, 214, 367–372. Kim, J.; Mhin, B. J.; Lee, S. J.; Kim, K. S. Chem. Phys. Lett. 1994, 219, 243-246 and references cited therein.
28. Jorgensen, W. L. J. Phys. Chem. 1983, 87, 5304-5314. Dean, P. M. Molecular Foundations of Drug-Receptor Interaction; Cambridge University Press: Cambridge, UK, 1987; pp 211f. Jorgensen, W. L. Chemtracts: Org. Chem. 1991, 4, 91-119 and references cited.
29. Born, M. Z. Phys. 1920, 1, 45–48. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127–6129.
30. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351–361.
31. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486–1493.
32. Tapia, O.; Goscinski, O. Mol. Phys. 1975, 29, 1653-1661. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. Pascual-Ahuir, J. L.; Silla, E.; Tomasi, J.; Bonaccorsi, R. J. Comp. Chem. 1987, 8, 778–787. Bianco, R.; Miertuš, S.; Persico, M.; Tomasi, J. Chem. Phys. 1992, 168, 281–292. Milne, G. W. A.; Nicklaus, M. C.; Hodoš ek, M. J. Mol. Struct. 1993, 291, 89–103. Olivares del Valle, F. J.; Aguilar, M. A.; Contador, J. C. Chem. Phys. 1993, 170, 161–165. Aguilar, M.; Bianco, R.; Miertus, S.; Persico, M.; Tomasi, J. Chem. Phys. 1993, 174, 397-407. Mingos, D. M. P.; Rohl, A. L.; Burgess, J. J. Chem. Soc., Dalton Trans. 1993, 423–426. Honig, B.; Sharp, K.; Yang, A.-S. J. Phys. Chem. 1993, 97, 1101–1109. Kim, H. J.; Bianco, R.; Gertner, B. J.; Hynes, J. T. J. Phys. Chem. 1993, 97, 1723–1728. Bachs, M.; Luque, F. J.; Orozco, M. J. Comput. Chem. 1994, 15, 446–454.
33. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991–8998. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776–4782.
34. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, S.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision B; Gaussian, Inc.: Pittsburgh, PA, 1992.
35. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645–1652. Cieplak, A. S.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 9226–9227. Parchment, O. G.; Hillier, I. H.; Green, D. V. S.; Burton, N. A.; Morley, J. O.; Schaefer, H. F., III J. Chem. Soc., Perkin Trans. 2 1992, 1681–1684. McDouall, J. J. W. J. Org. Chem. 1992, 57, 2861–2864. Wiberg, K. B.; Wong, M. W. J. Am. Chem. Soc. 1993, 115, 1078–1084. Tuñón, I.; Silla, E.; Tomasi, J. J. Phys. Chem. 1992, 96, 9043-9048. Parchment, O. G.; Green, D. V. S.; Taylor, P. J.; Hillier, I. H. J. Am. Chem. Soc. 1993, 115, 2352–2356. Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465–2472. Luque, F. J. J. Phys. Chem. 1993, 97, 9380–9384. Olivares del Valle, F. J.; Aguilar, M. A.; Tolosa, S. J. Mol. Struct. (Theochem) 1993, 279, 223-231. Young, P. E.; Hillier, I. H. Chem. Phys. Lett. 1993, 215, 405–408. Gould, I. R.; Hillier, I. H. J. Chem. Soc., Perkin Trans 2 1993, 1771–1773. Tortonda, F. R.; Pascual-Ahuir, J.-L.; Silla, E.; Tuñón, I. J. Phys. Chem. 1993, 97, 11087–11091.
36. Orozco, M.; Jorgensen, W. L.; Luque, F. J. J. Comput. Chem. 1993, 14, 1498-1503. Wiberg, K. B.; Marquez, M. J. Am. Chem. Soc. 1994, 116, 2197–2198.
37. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939–947.
38. Bigeleisen, J. J. Chem. Phys. 1949, 17, 675–678.
39. Wolfe, S.; Hoz, S.; Kim, C.-K.; Yang, K. J. Am. Chem. Soc. 1990, 112, 4186–4191.
40. Wolfe, S.; Kim, C.-K. J. Am. Chem. Soc. 1991, 113, 8056–8061.
41. Boyd, R. J.; Kim, C.-K.; Shi, Z.; Weinberg, N.; Wolfe, S. J. Am. Chem. Soc. 1993, 115, 10147–10152.
42. Aljibury, A. L.; Snyder, R. G.; Strauss, H. L.; Raghavachari, K. J. Chem. Phys. 1986, 84, 6872–6878.
43. Pupyshev, V. I.; Panchenko, Y. N.; Bock, C. W.; Pongor, G. J. Chem. Phys. 1991, 94, 1247–1252.
44. N2 Mechanism; Wiley-Interscience: New York, 1992; pp 80–84.
45. 0= x(HOH) + x(HOD)[k(DH)/2k(HH) + k(HD)/2k(HH)] + x(DOD)-k(DD)/k(HH), which is a more general version of eq 23 (vide infra), and used the mole fractions x calculated at the different atom fractions n, with K = 4.00 and 3.78, to obtain the proton inventories. There was no difference. (a) Friedman, L.; Shiner, V. J. J. Chem. Phys. 1966, 44, 4639-4640. Van Hook, W. A. J. Chem. Soc., Chem. Commun. 1972, 479–480.
46. Albery, W. J.; Davies, M. H. Trans. Faraday Soc. 1969, 65, 1059–1065.
47. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
48. Ventura, O. N.; Coitiño, E. L.; Irving, K.; Iglesias, A.; LLedós, A. J. Mol. Struct. (Theochem) 1990, 210, 427–440. Cook, D. B.; Sordo, T. L.; Sordo, J. A. J. Chem. Soc., Chem. Commun. 1990, 185–186. Åstrand, P.-O.; Wallqvist, A.; Karlström, G. J. Phys. Chem. 1991, 95, 6395–6396. Eggenberger, R.; Gerber, S.; Huber, H.; Searles, D. Chem. Phys. Lett. 1991, 183, 223–226. Valiron, P.; Vibók, A.; Mayer, I. J. Comput. Chem. 1993, 14, 401-409. Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 2488–2490. Dobado, J. A.; Molina, J. M. J. Phys. Chem. 1993, 97, 7499–7504. Davidson, E. R.; Chakravorty, S. J. Chem. Phys. Lett. 1993, 217, 48-56. Mayer, I.; Vibók, A.; Valiron, P. Chem. Phys. Lett. 1994, 224, 166–174. Wind, P.; Heully, J.-L. Chem. Phys. Lett. 1994, 230, 35-40. Neuheuser, T.; Hess, B. A.; Reutel, C.; Weber, E. J. Phys. Chem. 1994, 98, 6459–6467. Kieninger, M.; Suhai, S.; Mayer, I. Chem. Phys. Lett. 1994, 230, 485-490.
49. Wolfe, S.; Kim, C.-K. Isr. J. Chem. 1993, 33, 295–305.
50. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1936, 32, 877–879. Gross, P. Z. Elektrochem. 1938, 44, 299–301.
51. Orr, W. J. C.; Butler, J. A. V. J. Chem. Soc. 1937, 330–335.
52. Kresge, A. J. Pure Appl. Chem. 1964, 8, 243-258.
53. Gold, V. Adv. Phys. Org. Chem. 1969, 7, 259–331.
54. Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065–3067.
55. Mitchell, D. J.; Schlegel, H. B.; Shaik, S. S.; Wolfe, S. Can. J. Chem. 1985, 63, 1642–1648.
56. The authors are grateful to a Referee for drawing the work of Gandour (Gandour, R. D. Tetrahedron Lett. 1974, 295–298) to our attention.
57. Scheiner, S. Acc. Chem. Res. 1994, 27, 402–408.
58. Wolfe, S.; Kim, C.-K.; Yang, K. Can. J. Chem. 1994, 72, 1033-1043. For the application of these findings to the design of a novel antibacterial agent, see: Wolfe, S. Can. J. Chem. 1994, 72, 1014-1032. Wolfe, S.; Hoz, T. Can. J. Chem. 1994, 72, 1044–1050. Wolfe, S.; Jin, H.; Yang, K.; Kim, C.-K.; McEachern, E. Can. J. Chem. 1994, 72, 1051–1065. Wolfe, S.; Zhang, C.; Johnston, B. D.; Kim, C.-K. Can. J. Chem. 1994, 72, 1066–1075.
59. Hirschfelder, J. O.; Curtis, C. F.; Bird, R. B. Molecular Theory of Gases and Liquids: Wiley, New York, 1954.
60. Williams, I. H. J. Am. Chem. Soc. 1987, 109, 6299–6307.
61. Wertz, D. H. J. Am. Chem. Soc. 1980, 102, 5316–5322. See also: Abraham, M. H. J. Am. Chem. Soc. 1981, 103, 6742–6744.
62. Kubo, R. Statistical Mechanics; North Holland Publishers: Amsterdam, 1965.