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Thermal Stereomutations of Cyclopropane and of Isotopically Labeled Cyclopropanes Assessed through ab Initio Computational Methods and Kinetic Isotope Effect Calculations
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    Thermal Stereomutations of Cyclopropane and of Isotopically Labeled Cyclopropanes Assessed through ab Initio Computational Methods and Kinetic Isotope Effect Calculations
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    The Journal of Physical Chemistry

    Cite this: J. Phys. Chem. 1994, 98, 31, 7513–7522
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    https://doi.org/10.1021/j100082a021
    Published August 1, 1994

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    This article is cited by 36 publications.

    1. Weston Thatcher Borden . With a Little Help from My Friends: Forty Years of Fruitful Chemical Collaborations. The Journal of Organic Chemistry 2011, 76 (9) , 2943-2964. https://doi.org/10.1021/jo200213x
    2. Hongwei Zhou,, Ning-Bew Wong,, Kai-Chung Lau,, Anmin Tian, and, Wai-Kee Li. Discovery of Singlet Diradicals:  Theoretical Study on the Cage Species C14N12−H6 and Its Six Derivatives. The Journal of Physical Chemistry A 2007, 111 (39) , 9838-9847. https://doi.org/10.1021/jp072460l
    3. Jing Ma,, Yihong Ding,, Kazutaka Hattori, and, Satoshi Inagaki. Theoretical Designs of Singlet Localized 1,3-Diradicals. The Journal of Organic Chemistry 2004, 69 (12) , 4245-4255. https://doi.org/10.1021/jo035687v
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    5. William T. G. Johnson,, David A. Hrovat, and, Weston Thatcher Borden. Ab Initio Calculations on Spiropentane Stereomutations Lead to a Reinterpretation of the Experimental Results. Journal of the American Chemical Society 1999, 121 (34) , 7766-7772. https://doi.org/10.1021/ja9906305
    6. Kim Bolton and, William L. Hase, , Charles Doubleday, Jr.. A QM/MM Direct Dynamics Trajectory Investigation of Trimethylene Decomposition in an Argon Bath. The Journal of Physical Chemistry B 1999, 103 (18) , 3691-3698. https://doi.org/10.1021/jp982988d
    7. Anne Skancke,, David A. Hrovat, and, Weston Thatcher Borden. Ab Initio Calculations of the Effects of Geminal Silyl Substituents on the Stereomutation of Cyclopropane and on the Singlet−Triplet Splitting in Trimethylene. Journal of the American Chemical Society 1998, 120 (28) , 7079-7084. https://doi.org/10.1021/ja980720u
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    9. Feng Tian,, Scott B. Lewis,, Michael D. Bartberger,, William R. DolbierJr., and, Weston Thatcher Borden. Experimental Study of the Stereomutation of 1,1-Difluoro-2-ethyl-3-methylcyclopropane Confirms the Predicted Preference for Disrotatory Ring Opening and Closure. Journal of the American Chemical Society 1998, 120 (24) , 6187-6188. https://doi.org/10.1021/ja980969b
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    11. Faina Dubnikova and, Assa Lifshitz. Structural and Geometrical Isomerizations of Cyclopropane. Quantum Chemical and RRKM Calculations. The Journal of Physical Chemistry A 1998, 102 (19) , 3299-3306. https://doi.org/10.1021/jp980503f
    12. David A. Hrovat,, Shu Fang, and, Weston Thatcher Borden, , Barry K. Carpenter. Investigation of Cyclopropane Stereomutation by Quasiclassical Trajectories on an Analytical Potential Energy Surface. Journal of the American Chemical Society 1997, 119 (22) , 5253-5254. https://doi.org/10.1021/ja964238s
    13. Charles Doubleday, Jr., , Kim Bolton and, William L. Hase. Direct Dynamics Study of the Stereomutation of Cyclopropane. Journal of the American Chemical Society 1997, 119 (22) , 5251-5252. https://doi.org/10.1021/ja964250k
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    16. Faina Dubnikova, Assa Lifshitz. Quantum Chemical and Rate Constant Calculations of Thermal Isomerizations, Decompositions, and Ring Expansions of Organic Ring Compounds, Its Significance to Cohbusion Kinetics. 2011, 147-189. https://doi.org/10.1002/9781118166123.ch6
    17. John E. Baldwin. Thermal Stereomutations of Cyclopropanes and Vinylcyclopropanes. 2009https://doi.org/10.1002/9780470682531.pat0035
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    19. Yong Wang, Jing Ma, Satoshi Inagaki. Stable silicon‐centered localized singlet 1,3‐diradicals XSi(GeY 2 ) 2 SiX: theoretical predictions. Journal of Physical Organic Chemistry 2007, 20 (9) , 649-655. https://doi.org/10.1002/poc.1221
    20. David K. Lewis, Steven V. Hughes, Justine D. Miller, Jessica Schlier, Kevin A. Wilkinson, Sara R. Wilkinson, Bansi L. Kalra. Kinetics of the thermal isomerization of 1,1,2‐trimethylcyclopropane. International Journal of Chemical Kinetics 2006, 38 (8) , 475-482. https://doi.org/10.1002/kin.20184
    21. John E. Baldwin, Jean-Marie Fedé. Thermal Isomerizations of 2- d -1-( E )-Propenylcyclobutanes to 4- d -3-Methylcyclohexenes. Journal of the American Chemical Society 2006, 128 (17) , 5608-5609. https://doi.org/10.1021/ja0586586
    22. John E Baldwin, Stephanie R Singer. Deuterium kinetic isotope effects on the thermal isomerizations of deuteriocyclopropane to deuterium-labeled propenes. Canadian Journal of Chemistry 2005, 83 (9) , 1510-1515. https://doi.org/10.1139/v05-167
    23. Yong Wang, Jing Ma, Satoshi Inagaki. Theoretical design of singlet localized σ-diradicals: C(MH2)3C (M=Si, Ge, Sn, Pb). Tetrahedron Letters 2005, 46 (33) , 5567-5571. https://doi.org/10.1016/j.tetlet.2005.06.064
    24. Christine Isborn, David A. Hrovat, Weston Thatcher Borden. Does Formation of Singlet Propane-1,3-diyl from Propane Deviate from Bond Enthalpy Additivity? Results of Ab Initio Calculations That Bear on the Existence of the Benson Barrier to Diradical Ring Closure. The Journal of Physical Chemistry A 2004, 108 (15) , 3024-3029. https://doi.org/10.1021/jp036867b
    25. Barry K. Carpenter. Nonexponential decay of reactive intermediates: new challenges for spectroscopic observation, kinetic modeling and mechanistic interpretation. Journal of Physical Organic Chemistry 2003, 16 (11) , 858-868. https://doi.org/10.1002/poc.672
    26. Mayra B. Reyes, Emil B. Lobkovsky, Barry K. Carpenter. Interplay of Orbital Symmetry and Nonstatistical Dynamics in the Thermal Rearrangements of Bicyclo[ n .1.0]polyenes. Journal of the American Chemical Society 2002, 124 (4) , 641-651. https://doi.org/10.1021/ja017083j
    27. Wilhelm Graf von der Schulenburg, Henning Hopf, Robin Walsh. Alkyl-Wanderungstendenzen bei der Vinyliden-Acetylen-Umlagerung und Isotopeneffekt in der Vinylidenbildung aus einem deuterierten Cyclopropen. Angewandte Chemie 1999, 111 (8) , 1200-1203. https://doi.org/10.1002/(SICI)1521-3757(19990419)111:8<1200::AID-ANGE1200>3.0.CO;2-W
    28. Scott B. Lewis, David A. Hrovat, Stephen J. Getty, Weston Thatcher Borden. Ab Initio calculations of the potential surfaces for rearrangement of methylenecyclopropane and 2,2-difluoromethylenecyclopropane. Why do the geminal fluorines have little effect on lowering the activation energy? †. J. Chem. Soc., Perkin Trans. 2 1999, 14 (11) , 2339-2347. https://doi.org/10.1039/A902739D
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    32. Kang-Nian Fan, Zhen-Hua Li, Wen-Ning Wang, Hsing-Hua Huang, Wei Huang. A theoretical study on the isomerization of cyclopropane to propene with ab initio and DFT methods. Chemical Physics Letters 1997, 277 (1-3) , 257-263. https://doi.org/10.1016/S0009-2614(97)00905-6
    33. Per N. Skancke, David A. Hrovat, Weston Thatcher Borden. Ab Initio Calculations on the Preferred Mode of Ring Opening in Silacyclopropane. Journal of the American Chemical Society 1997, 119 (34) , 8012-8014. https://doi.org/10.1021/ja964384y
    34. Kim Bolton, William L. Hase, Charles Doubleday. Isomerisation of deuterated cyclopropanes — The possibility for stereochemical control. Berichte der Bunsengesellschaft für physikalische Chemie 1997, 101 (3) , 414-422. https://doi.org/10.1002/bbpc.19971010314
    35. John E. Baldwin, Teresa B. Freedman, Yukio Yamaguchi, Henry F. Schaefer. Secondary Deuterium Kinetic Isotope Effects on the Isomerization of the Trimethylene Diradical to Cyclopropane. Journal of the American Chemical Society 1996, 118 (44) , 10934-10935. https://doi.org/10.1021/ja962083i
    36. S. Pedersen, J. L. Herek, A. H. Zewail. The Validity of the "Diradical" Hypothesis: Direct Femtoscond Studies of the Transition-State Structures. Science 1994, 266 (5189) , 1359-1364. https://doi.org/10.1126/science.266.5189.1359

    The Journal of Physical Chemistry

    Cite this: J. Phys. Chem. 1994, 98, 31, 7513–7522
    Click to copy citationCitation copied!
    https://doi.org/10.1021/j100082a021
    Published August 1, 1994

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