Theoretical predictions and comparison with experiment

Molecules

Volumn 18, Issue 2, 2013, Pages 2281-2296

  Fong, Aaron ^a   Meyer, Matthew P ^b   O'Leary, Daniel J ^a  

^a POMONA COLLEGE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Bigeleisen Mayer formalism; Conformational kinetic isotope effect; Enthalpy entropy contributions to isotope effects; Steric isotope effect

Indexed keywords

1,1' BINAPHTHYL; 1,1'-BINAPHTHYL; BIPHENYL; BIPHENYL DERIVATIVE; ISOTOPE; NAPHTHALENE DERIVATIVE; PHENANTHRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; COMPUTER SIMULATION; CONFORMATION; ENTROPY; KINETICS; THEORETICAL MODEL;

BIPHENYL COMPOUNDS; COMPUTER SIMULATION; ENTROPY; ISOTOPES; KINETICS; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR CONFORMATION; NAPHTHALENES; PHENANTHRENES;

MLCS; MLOWN;

EID: 84874582042     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18022281     Document Type: Article

References (28)

1. Perrin, C.L.; Thoburn, J.D.; Kresge, A.J. Secondary kinetic isotope effects in C-N rotation of amides. J. Am. Chem. Soc. 1992, 114, 8800-8807.
2. Olson, L.P.; Li, Y.; Houk, K.N.; Kresge, A.J.; Schaad, L.J. Theoretical analysis of secondary kinetic isotope effects in C-N rotation of amides. J. Am. Chem. Soc. 1995, 117, 2992-2997.
3. Parkin, G. Applications of deuterium isotope effects for probing aspects of reactions involving oxidative addition and reductive elimination of H-H and C-Hh bonds. J. Labelled Compd. Rad. 2007, 50, 1088-1114.
4. O'Leary, D.J.; Hickstein, D.D.; Hansen, B.K.; Hansen, P.E. Theoretical and NMR studies of deuterium isotopic perturbation of hydrogen bonding in symmetrical dihydroxy compounds. J. Org. Chem. 2010, 75, 1331-1342.
5. O'Leary, D.J.; Rablen, P.R.; Meyer, M.P. On the origin of conformational kinetic isotope effects. Angew Chem. Int. Ed. 2011, 50, 2564-2567.
6. Bartell, L.S. Role of non-bonded repulsions in secondary isotope effects. 1. Alpha and beta substitution effects. J. Am. Chem. Soc. 1961, 83, 3567-3571.
7. Bigeleisen, J.; Mayer, M.G. Calculation of equilibrium constants for isotopic exchange reactions. J. Chem. Phys. 1947, 15, 261-267.
8. Saunders, M.; Laidig, K.E.; Wolfsberg, M. Theoretical calculation of equilibrium isotope effects using abinitio force-constants: Application to NMR isotopic perturbation studies. J. Am. Chem. Soc. 1989, 111, 8989-8994. (Pubitemid 20067519)
9. Mislow, K.; Simon, E.; Hopps, H.B. A secondary kinetic isotope effect in conformational racemization. Tetrahedron Lett. 1962, 1011-1014.
10. Mislow, K.; Simon, E.; Glass, M.A.W.; Wahl, G.H.; Hopps, H.B. Stereochemistry of doubly bridged biphenyls: Synthesis, spectral properties, and optical stability. J. Am. Chem. Soc. 1964, 86, 1710-1733.
11. Dunitz, J.D.; Ibberson, R.M. Is deuterium always smaller than protium? Angew. Chem. Int. Ed. 2008, 47, 4208-4210.
12. Mislow, K.; Graeve, R.; Gordon, A.J.; Wahl, G.H. A note on steric isotope effects. Conformational kinetic isotope effects in the racemization of 9,10-dihydro-4,5-dimethylphenanthrene. J. Am. Chem. Soc. 1963, 85, 1199-1200.
13. Mislow, K.; Wahl, G.H.; Gordon, A.J.; Graeve, R. Conformational kinetic isotope effects in racemization of 9,10-dihydro-4,5-dimethylphenanthrene. J. Am. Chem. Soc. 1964, 86, 1733-1741.
14. Hayama, T.; Baldridge, K.K.; Wu, Y.T.; Linden, A.; Siegel, J.S. Steric isotope effects gauged by the bowl-inversion barrier in selectively deuterated pentaarylcorannulenes. J. Am. Chem. Soc. 2008, 130, 1583-1591. (Pubitemid 351214076)
15. Mugridge, J.S.; Bergman, R.G.; Raymond, K.N., Does size really matter? The steric isotope effect in a supramolecular host-guest exchange reaction. Angew. Chem. Int. Ed. 2010, 49, 3635-3637.
16. West, J.D.; Stafford, S.E.; Meyer, M.P. A mechanistic probe for asymmetric reactions: Deuterium isotope effects at enantiotopic groups. J. Am. Chem. Soc. 2008, 130, 7816-7817. (Pubitemid 351875044)
17. Meyer, M.P. Nonbonding interactions and stereoselection in the Corey-Bakshi-Shibata reduction. Org. Lett. 2009, 11, 4338-4341.
18. Giagou, T.; Meyer, M.P. Kinetic isotope effects in asymmetric reactions. Chem.-Eur. J. 2010, 16, 10616-10628.
19. Sherrod, S.A.; Boekelheide, V. Unusually large conformational kinetic isotope-effect in [2.2]metaparacyclophane. J. Am. Chem. Soc. 1972, 94, 5513-5515.
20. Sherrod, S.A.; Costa, R.L.D.; Barnes, R.A.; Boekelheide, V. Study of steric effects in [2.2]metaparacyclophanes: Steric isotope-effect, remote substituent effects on a steric barrier, and other steric phenomena. J. Am. Chem. Soc. 1974, 96, 1565-1577.
21. Irikura, K.K.; Johnson, R.D.; Kacker, R.N.; Kessel, R. Uncertainties in scaling factors for ab initio vibrational zero-point energies. J. Chem. Phys. 2009, 130, 114102-114111.
22. Carter, R.E.; Dahlgren, L. Steric isotope effects. 3. The deuterium isotope effect in racemization of (-)-1,1'-binaphthyl-2,2'-d2. Acta Chem. Scand. 1969, 23, 504-514.
23. Melander, L.; Carter, R.E. Steric isotope effects. The isotope effect on racemization of 2,2'-dibromo-4,4'-dicarboxybiphenyl. J. Am. Chem. Soc. 1964, 86, 295-296.
24. Hall, D.M.; Harris, M.M. Some racemisation data for compounds owing their optical activity to restricted rotation. J. Chem. Soc. 1960, 490-494.
25. Heitner, C.; Leffek, K.T. Deuterium isotope effect on racemization of a highly hindered biphenyl derivative. Can. J. Chem. 1966, 44, 2567-2570.
26. Carter, R.E.; Dahlgren, L. Steric isotope effects. 4. Deuterium isotope effect in racemization of (+)-2-(N,N,N-trimethyl)-2'-(N,N-dimethyl)-diamino- biphenyl-6,6'-d2 cation. Acta Chem. Scand. 1970, 24, 633-643.
27. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; et al. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, USA, 2009.
28. Hirschi, J.S.; Takeya, T.; Hang, C.; Singleton, D.A. Transition-state geometry measurements from C-13 isotope effects. The experimental transition state for the epoxidation of alkenes with oxaziridines. J. Am. Chem. Soc. 2009, 131, 2397-2403.