The Influence of Water on the Rates of 1,3-Dipolar Cycloaddition Reactions:  Trigger Points for Exponential Rate Increases in Water−Organic Solvent Mixtures. Water-Super versus Water-Normal Dipolarophiles

Richard N. Butler; William J. Cunningham; Anthony G. Coyne; Luke A. Burke

doi:10.1021/ja040119y

journal article Sep 01, 2004

The Influence of Water on the Rates of 1,3-Dipolar Cycloaddition Reactions: Trigger Points for Exponential Rate Increases in Water−Organic Solvent Mixtures. Water-Super versus Water-Normal Dipolarophiles

Richard N. Butler William J. Cunningham Anthony G. Coyne Luke A. Burke

Journal of the American Chemical Society Vol. 126 No. 38 pp. 11923-11929 · American Chemical Society (ACS)

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References

40

[1]

Breslow R. Acc. Chem. Res. (1991) 10.1021/ar00006a002

[2]

Biscoe M. R. J. Am. Chem. Soc. (2003) 10.1021/ja0379924

[3]

Engberts J. B. F. N. J. Chem. Commun. (2001)

[4]

Breslow R. J. Am. Chem. Soc. (1980) 10.1021/ja00546a049

[5]

Otto S. Pure Appl. Chem. (2000) 10.1351/pac200072071365

[6]

Otto S. Org. Biomol. Chem. (2003) 10.1039/b305672d

[7]

Engberts J. B. F. N. Pure Appl. Chem. (1995)

[8]

Garner P. (1998)

[9]

Cave G. W. V. Chem. Commun. (2001)

[10]

van Mersbergen D. J. Org. Chem. (1998) 10.1021/jo980900m

[11]

Inoue Y. Bull. Chem. Soc. Jpn. (1991)

[12]

Dignam J. J. J. Org. Chem. (1978) 10.1021/jo00397a002

[13]

Molteni G. J. Chem. Soc., Perkin Trans. 1 (2000)

[14]

Ponti A. New J. Chem. (2002) 10.1039/b205071d

[15]

Molteni G. New J. Chem. (2002) 10.1039/b205063c

[16]

Butler R. N. J. Chem. Soc., Perkin Trans. 2 (2002)

[17]

Gholami M. R. J. Chem. Res.(S) (1999)

[18]

Blake J. F. J. Org. Chem. (1994) 10.1021/jo00083a021

[19]

QM/MM Simulations for Diels−Alder Reactions in Water: Contribution of Enhanced Hydrogen Bonding at the Transition State to the Solvent Effect

Jayaraman Chandrasekhar, Shane Shariffskul, William L. Jorgensen

The Journal of Physical Chemistry B 2002 10.1021/jp020326p

[20]

Furlani T. R. J. Org. Chem. (1996) 10.1021/jo9518011

[21]

Otto S. J. Org. Chem. (1994) 10.1021/jo00097a045

[22]

Breslow R. J. Am. Chem. Soc. (2002) 10.1021/ja012293h

[23]

Breslow R. Tetrahedron Lett. (1984)

[24]

Breslow R. J. Am. Chem. Soc. (1995)

[25]

Blokzigl W. J. Am. Chem. Soc. (1991)

[26]

Breslow R. J. Am. Chem. Soc. (1995)

[27]

Breslow R. J. Am. Chem. Soc. (1995)

[28]

Breslow R. J. Am. Chem. Soc. (1996)

[29]

Breslow R. J. Am. Chem. Soc. (1991) 10.1021/ja00011a053

[30]

Frisch M. J. (2003)

[31]

Becke A. D. J. Chem. Phys. (1993)

[32]

Lee C. Phys. Rev. (1988)

[33]

Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr

Burkhard Miehlich, Andreas Savin, Hermann Stoll et al.

Chemical Physics Letters 1989 10.1016/0009-2614(89)87234-3

[34]

Hehre W. J. J. Chem Phys. (1972)

[35]

The influence of polarization functions on molecular orbital hydrogenation energies

P. C. Hariharan, J. A. Pople

Theoretica Chimica Acta 1973 10.1007/bf00533485

[36]

Flükiger P. (2000)

[37]

How Strong Is the Cα−H···OC Hydrogen Bond?

Rubicelia Vargas, Jorge Garza, David A. Dixon et al.

Journal of the American Chemical Society 2000 10.1021/ja993600a

[38]

Domingo L. R. J. Org. Chem. (2003)

[39]

Butler R. N. J. Chem. Res. (S) (1996)

[40]

Vogel A. (1989)

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Details

Published: Sep 01, 2004
Vol/Issue: 126(38)
Pages: 11923-11929

Authors

R

Richard N. Butler

Chemistry Department, National University of Ireland, Galway, Ireland, and Chemistry Department, Rutgers University, Camden, New Jersey 08102

W

William J. Cunningham

Chemistry Department, National University of Ireland, Galway, Ireland, and Chemistry Department, Rutgers University, Camden, New Jersey 08102

A

Anthony G. Coyne

Chemistry Department, National University of Ireland, Galway, Ireland, and Chemistry Department, Rutgers University, Camden, New Jersey 08102

L

Luke A. Burke

Chemistry Department, National University of Ireland, Galway, Ireland, and Chemistry Department, Rutgers University, Camden, New Jersey 08102

Cite This Article

Richard N. Butler, William J. Cunningham, Anthony G. Coyne, et al. (2004). The Influence of Water on the Rates of 1,3-Dipolar Cycloaddition Reactions: Trigger Points for Exponential Rate Increases in Water−Organic Solvent Mixtures. Water-Super versus Water-Normal Dipolarophiles. Journal of the American Chemical Society, 126(38), 11923-11929. https://doi.org/10.1021/ja040119y

The Influence of Water on the Rates of 1,3-Dipolar Cycloaddition Reactions: Trigger Points for Exponential Rate Increases in Water−Organic Solvent Mixtures. Water-Super versus Water-Normal Dipolarophiles

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