Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

Matthias K. Diedrich; Frank Gerrit Klärner; Brett R. Beno; K. N. Houk; Hanoch Senderowitz; W. Clark Still

doi:10.1021/ja9643331

Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

Matthias K. Diedrich, Frank Gerrit Klärner, Brett R. Beno, K. N. Houk, Hanoch Senderowitz, W. Clark Still

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Abstract

Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.

Original language	English
Pages (from-to)	10255-10259
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	119
Issue number	43
DOIs	https://doi.org/10.1021/ja9643331
State	Published - 1997
Externally published	Yes

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Diedrich, M. K., Klärner, F. G., Beno, B. R., Houk, K. N., Senderowitz, H., & Still, W. C. (1997). Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method. Journal of the American Chemical Society, 119(43), 10255-10259. https://doi.org/10.1021/ja9643331

Diedrich, Matthias K. ; Klärner, Frank Gerrit ; Beno, Brett R. et al. / Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method. In: Journal of the American Chemical Society. 1997 ; Vol. 119, No. 43. pp. 10255-10259.

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title = "Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method",

abstract = "Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.",

author = "Diedrich, {Matthias K.} and Kl{\"a}rner, {Frank Gerrit} and Beno, {Brett R.} and Houk, {K. N.} and Hanoch Senderowitz and Still, {W. Clark}",

year = "1997",

doi = "10.1021/ja9643331",

language = "אנגלית",

volume = "119",

pages = "10255--10259",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "43",

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Diedrich, MK, Klärner, FG, Beno, BR, Houk, KN, Senderowitz, H & Still, WC 1997, 'Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method', Journal of the American Chemical Society, vol. 119, no. 43, pp. 10255-10259. https://doi.org/10.1021/ja9643331

Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method. / Diedrich, Matthias K.; Klärner, Frank Gerrit; Beno, Brett R. et al.
In: Journal of the American Chemical Society, Vol. 119, No. 43, 1997, p. 10255-10259.

Research output: Contribution to journal › Article › peer-review

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AB - Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.

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Diedrich MK, Klärner FG, Beno BR, Houk KN, Senderowitz H, Still WC. Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method. Journal of the American Chemical Society. 1997;119(43):10255-10259. doi: 10.1021/ja9643331

Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

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