A computational study of the formation of 1,3,2-dioxaborolane from the reaction of dihydroxy borane with 1,2-ethanediol

Journal of Molecular Structure: THEOCHEM

Volumn 673, Issue 1-3, 2004, Pages 145-154

  Bhat, Krishna L ^a   Hayik, Seth ^a   Corvo, Joseph N ^a   Marycz, Damien M ^a   Bock, Charles W ^a  

^a THOMAS JEFFERSON UNIVERSITY   (United States)

Author keywords

Carbohydrates; Dehydration; Glycoprotein

Indexed keywords

1,3,2 DIOXABOROLANE; ACETONITRILE; BASE; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; DIHYDROXYBORANE; ESTER DERIVATIVE; ETHYLENE GLYCOL; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; MOLECULAR MECHANICS; PARAMETER; REACTION ANALYSIS; THERMODYNAMICS;

EID: 1442323981     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2003.11.045     Document Type: Article

References (96)

1. Yoon J., Czarnick A.W. J. Am. Chem. Soc. 114:1992;5874.
2. James T.D., Sandanayake K.R.A.S., Shinkai S. J. Chem. Soc., Chem. Commum. 1994;477.
3. Lavigne J.J., Anslyn E.V. Angew. Chem. Int. Ed. 38:1999;3666.
4. C.J. Ward, P. Patel, P.R. Ashton, T.D. James, Chem. Commun. (2000) 229.
5. James T.D., Shinkai S. Top. Curr. Chem. 218:2002;159.
6. James T.D., Sandanayake K.R.A.S., Iguchi R., Shinkai S. J. Am. Chem. Soc. 117:1995;8982.
7. Eggert H., Frederiksen J., Morin C., Norrild J.C. J. Org. Chem. 64:1999;3846.
8. James T.D., Sandanayake K.R.A.S., Shinkai S. Angew. Chem. Int. Ed. Engl. 35:1996;1910.
9. Wang W., Gao S., Wang B. Org. Lett. 1:1999;1209.
10. Yoon J., Czarnick A.W. J. Am. Chem. Soc. 114:1992;5874.
11. Adhikiri D.P., Heagy M.D. Tetrahedron Lett. 40:1999;7893.
12. Arimori S., Bosch L.I., Ward C.J., James T.D. Tetrahedron Lett. 42:2001;4553.
13. Cabell L.A., Monahan M.K., Anslyn E.V. Tetrahedron Lett. 40:1999;7753.
14. Yang W., He H., Drueckhammer D.G. Angew. Chem. Int. Ed. 40:2001;1714.
15. Draffin S.P., Duggan P.J., Duggan S.A.M. Org. Lett. 3:2001;917.
16. Gardiner S., Smith B., Duggan P., Karpa M., Griffin G. Tetrahedron. 55:1999;2857.
17. Karpa M., Duggan P., Griffin G., Freudigmann S. Tetrahedron. 53:1997;3669.
18. Mohler L.K., Czarnick A.W. J. Am. Chem. Soc. 115:1993;2998.
19. Paugam M.F., Bien J.T., Smith B.D., Chrisstoffels L.A.J., de Jong F., Reinhoudt D.N. J. Am. Chem. Soc. 118:1996;9820.
20. Riggs J.A., Hossler K.A., Smith B.D., Karpa M.J., Griffin G., Duggan P.J. Tetrahedron Lett. 37:1996;6303.
21. Smith B.D., Gardiner S.J., Munro T.A., Paugam M.F., Riggs J.A. J. Incl. Phenom. Mol. Recogn. Chem. 32:1998;121.
22. Westmark P.R., Gardiner S.J., Smith B. J. Am. Chem. Soc. 118:1996;11093.
23. Adamek V., Liu X.C., Zhang Y.A., Adamkova K., Scouten W.H. J. Chromatogr. 625:1992;91.
24. Bergold A., Scouten W.H. Chem. Anal. (NY). 66:1983;149.
25. Bouriotis V., Galpin J., Dean P.D.G. J. Chromatogr. 210:1981;267.
26. Liu X., Hubbard J., Scouten W. J. Organomet. Chem. 493:1995;91.
27. Psotova J., Janiczek O. Chem. Listy. 89:1995;641.
28. Seliger H., Genrich V. Experientia. 30:1974;1480.
29. Singhal R., DeSilva S. Giddings J., Grushka E., Brown P. Advanced Chromatography. vol. 31:1992;293 Marcel Dekker, New York.
30. Westmark P.R., Valencia L.S., Smith B.D. J. Chromatogr. A. 664:1994;123.
31. Ranade V.V., Hollinger M.A. Drug Delivery Systems. 1995;CRC Press, Boca Raton, FL.
32. Friden P.M., Walus L.R., Musso G.F., Taylor M.A., Malfroy B., Starzyk R.M. Proc. Natl Acad. Sci. 88:1991;4771.
33. Kuan C.T., Pastan I. Proc. Natl Acad. Sci. 93:1996;974.
34. Bagshawe K.D. Drug Dev. Res. 34:1995;220.
35. Springer C.J., Niculescu-Duvaz I., Pedley R.B. J. Med. Chem. 37:1994;2361.
36. Tiefenauer L.X., Kuhne G., Andrea R.Y. Bioconjugate Chem. 4:1993;347.
37. Wu G.X., He G.R., Wu J.C., Ruan C.G. Chin. Med. J. 105:1992;553.
38. Butle J.W.M., Hoeckstra Y., Kamman R.L., Magin R.L., Webb A.G., Briggs R.W., Go K.G., Hulstaert C.E., Miltenyi S., The T.H., De Leij L. Magn. Reson. Med. 25:1992;148.
39. Gao S., Wang W., Wang B. Bioorg. Chem. 29:2001;308.
40. Morandi F., Caselli E., Morandi S., Focia P.J., Blazquez J., Shoichet B.K., Prati F. J. Am. Chem. Soc. 125:2003;685.
41. Van Duin M., Peters J.A., Kieboom A.P.G., Van Bekkum H. Tetrahedron. 40:1984;2901.
42. Van Duin M., Peters J.A., Kieboom A.P.G., Van Bekkum H. Tetrahedron. 41:1985;3411.
43. Kustin K., Pizer R.D. J. Am. Chem. Soc. 91:1969;317.
44. Pizer R.D., Ricatto P.J., Tihal C.A. Polyhedron. 12:1993;2137.
45. Pizer R.D., Tihal C.A. Inorg. Chem. 31:1992;3243.
46. Pizer R.D., Ricatto P.J. Inorg. Chem. 33:1994;2402.
47. Weser V. Struct. Bonding (Berlin). 2:1967;160.
48. Lauer M., Wulff G. J. Organomet. Chem. 256:1983;1.
49. Brown H.C., Vara J.V.N. Prasad. J. Org. Chem. 51:1986;4526.
50. Wiskur S.L., Lavigne J.L., Haddou H.A., Lynch V., Chiu Y.H., Canary J.W., Anslyn E.V. Org. Letts. 2:2001;1311.
51. Wulff G. Pure Appl. Chem. 54:1982;2093.
52. Bierdrzycki M., Scouten W.H., Biedrzycka Z. J. Organomet. Chem. 431:1992;255. and references cited therein.
53. Mozurkewich M., Benson S.W. J. Phys. Chem. 88:1984;6429.
54. Mozurkewich M., Lamb J.J., Benson S.W. J. Phys. Chem. 88:1984;6435.
55. Lamb J.J., Mozurkewich M., Benson S.W. J. Phys. Chem. 88:1984;6441.
56. Bhat K.L., Hayik S., Bock C.W. J. Mol. Struct. (Theochem). 638:2003;107.
57. S.H. Ross, Ph.D. Thesis, The Ohio State University, 1961.
58. Springsteen G., Wang B. Tetrahedron. 58:2002;5291.
59. Becke A.D. J. Chem. Phys. 98:1993;5648.
60. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785.
61. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Q. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Lui, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Kieth, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, P.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A-7, Gaussian Inc., Pittsburgh, PA, 1998.
62. Gordon M.S. Chem. Phys. Lett. 76:1980;163.
63. Hariharan P.C., Pople J.A. Theor. Chim. Acta. 28:1973;213.
64. Hehre W.J., Ditchfield R., Pople J.A. J. Chem. Phys. 56:1972;2257.
65. Hehre W.J., Radom L., Schleyer P.V.R., Pople J.A. Ab Initio Molecular Orbital Theory. 1986;Wiley, New York.
66. Møller C., Plesset M.S. Phys. Rev. 46:1934;618.
67. Cizek J. Adv. Chem. Phys. 14:1969;35.
68. Purvis G.D., Bartlet R.J. J. Chem. Phys. 76:1982;1910.
69. Scuseria G.E., Janssen C.L., Scheafer H.F. III. J. Chem. Phys. 89:1988;7382.
70. Scuseria G.E., Schaefer H.F. III. J. Chem. Phys. 90:1989;3700.
71. Pople J.A., Head-Gordon M., Raghavachari K. J. Chem. Phys. 87:1987;5968.
72. Carpenter J.E., Weinhold F. J. Mol. Struct. (Theochem). 169:1988;41.
73. Foster J.P., Weinhold F. J. Am. Chem. Soc. 102:1980;7211.
74. Reed A.E., Weinhold F. J. Chem. Phys. 78:1983;4066.
75. Reed A.E., Weinstock R.B., Weinhold F. J. Chem. Phys. 83:1985;735.
76. Reed A.E., Curtiss L.A., Weinhold F. Chem. Rev. 88:1988;899.
77. Jaguar 4.1, Release 45, Schrödinger, Inc., Portland, OR, 1991-2000.
78. McKee M. J. Phys. Chem. 100:1996;8260.
79. Kawashima Y., Takeo H., Matsumura C. J. Chem. Phys. 74:1981;5430.
80. Kawashima Y., Takeo H., Matsumura C. Chem. Phys. Lett. 57:1978;145.
81. 2 can form a hydrogen-bonded dimer (as opposed to a diborane-like dimer) which is bound by some 11.4 kcal/ mol in vacuo. We have only considered monomeric forms of the boron compounds in this study to simplify the underlying PES.
82. Wong M.W., Frisch M.J., Wiberg K.B. J. Am. Chem. Soc. 113:1991;4776.
83. Wong M.W., Wiberg K.B., Frisch M.J. J. Am. Chem. Soc. 114:1992;523.
84. Wong M.W., Wiberg K.B., Frisch M.J. J. Am. Chem. Soc. 114:1992;1645.
85. Cieplak A.S., Wiberg K.B. J. Am. Chem. Soc. 115:1993;1078.
86. Foresman J.B., Wong M.W., Wiberg K.B., Frisch M.J. J. Am. Chem. Soc. 115:1993;2220.
87. Wiberg K.B., Marquez M. J. Am. Chem. Soc. 116:1994;2197.
88. Wiberg K.B., Keith T.A., Frisch M.J., Murcko M.J. J. Phys. Chem. 99:1995;9072.
89. Wiberg K.B., Rablen P.R., Rush D.J., Keith T.A. J. Am. Chem. Soc. 117:1995;4261.
90. Wiberg K.B., Castejon H., Keith T.A. J. Comp. Chem. 17:1996;185.
91. Gonzalez C., Restrepo-Cossio A., Marquez M., Wiberg K.B. J. Am. Chem. Soc. 118:1996;8291.
92. Castejon H., Wiberg K.B. J. Am. Chem. Soc. 121:1999;2139.
93. Castejon H., Wiberg K.B., Skenak S., Hinz W. J. Am. Chem. Soc. 123:2001;6092.
94. 0, +4.6 and -3.3 kcal/mol, respectively, are only slightly lower than the corresponding values in vacuo.
95. Wade L.G. Organic Chemistry. 5th ed. 2000;Prentice Hall, Upper Saddle River, NJ. p. 814.
96. ‡ from +32.5 to +33.0 kcal/mol.