Capture of hydroxymethylene and its fast disappearance through tunnelling

Nature

Volumn 453, Issue 7197, 2008, Pages 906-909

  Schreiner, Peter R ^a   Reisenauer, Hans Peter ^a   Pickard Iv, Frank C ^b   Simmonett, Andrew C ^b   Allen, Wesley D ^b   Mátyus, Edit ^c   Császár, Attila G ^c  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBENOID; CARBOHYDRATE DERIVATIVE; CARBON; FORMALDEHYDE; GLYOXYLIC ACID; HYDROXYMETHYLENE; TRANSITION ELEMENT;

CARBOHYDRATE; CARBON; FORMALDEHYDE; HYDROGEN; TUNNELING;

ARTICLE; ELECTRON TRANSPORT; PHOTOCATALYSIS; PRIORITY JOURNAL;

EID: 45149124881     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature07010     Document Type: Article

References (57)

1. Bourissou, D., Guerret, O., Gabbaï, F. P. & Bertrand, G. Stable carbenes. Chem. Rev. 100, 39-91 (2000).
2. Nolan, S. P. N-Heterocyclic Carbenes in Synthesis (Wiley-VCH, Weinheim, 2006).
3. Kemper, M. J. H., Vandijk, J. M. F. & Buck, H. M. Ab initio calculation on the photochemistry of formaldehyde. The search for a hydroxycarbene intermediate. J. Am. Chem. Soc. 100, 7841-7846 (1978).
4. Lucchese, R. R. & Schaefer, H. F. Metal-carbene complexes and the possible role of hydroxycarbene in formaldehyde laser photochemistry. J. Am. Chem. Soc. 100, 298-299 (1978).
5. Hoffmann, M. R. & Schaefer, H. F. Hydroxycarbene (HCOH) and protonated formaldehyde: Two potentially observable interstellar molecules. Astrophys. J. 249, 563-565 (1981).
6. Reid, D. L., Hernández-Trujillo, J. & Warkentin, J. A theoretical study of hydroxycarbene as a model for the homolysis of oxy- and dioxycarbenes. J. Phys. Chem. A 104, 3398-3405 (2000).
7. Goddard, J. D. & Schaefer, H. F. The photodissociation of formaldehyde: Potential energy surface features. J. Chem. Phys. 70, 5117-5134 (1979).
8. Baly, E. C. C., Heilbron, I. M. & Barker, W. F. CX. - Photocatalysis. Part I. The synthesis of formaldehyde and carbohydrates from carbon dioxide and water. J. Chem. Soc. Trans. 119, 1025-1035 (1921).
9. Sierra, M. A. Di- and polymetallic heteroatom stabilized (Fischer) metal carbene complexes. Chem. Rev. 100, 3591-3637 (2000).
10. Pau, C.-F. & Hehre, W. J. Relative thermochemical stabilities of hydroxymethylene and formaldehyde by ion cyclotron double resonance spectroscopy. J. Phys. Chem. 86, 1252-1253 (1982).
11. Fischer, E. O. & Maasböl, A. On existence of tungsten carbonyl carbene complex. Angew. Chem. Int. Edn Engl. 3, 580-581 (1964).
12. Weiner, B. R. & Rosenfeld, R. N. Pyrolysis of pyruvic acid in the gas phase. A study of the isomerization mechanism of a hydroxycarbene intermediate. J. Org. Chem. 48, 5362-5364 (1983).
13. Rosenfeld, R. N. & Weiner, B. Energy disposal in the photofragmentation of pyruvic acid in the gas phase. J. Am. Chem. Soc. 105, 3485-3488 (1983).
14. Jacox, M. E. The spectroscopy of molecular reaction intermediates trapped in the solid rare gases. Chem. Soc. Rev. 31, 108-115 (2002).
15. Evangelista, F. A., Allen, W. D. & Schaefer, H. F. Coupling term derivation and general implementation of state-specific multireference coupled cluster theories. J. Chem. Phys. 127, 024102 (2007).
16. Császár, A. G., Allen, W. D. & Schaefer, H. F. In pursuit of the ab initio limit for conformational energy prototypes. J. Chem. Phys. 108, 9751-9764 (1998).
17. Schreiner, P. R. & Reisenauer, H. P. The "non-reaction" of ground-state triplet carbon atoms with water revisited. ChemPhysChem 7, 880-885 (2006).
18. Venkateswarlu, P. & Gordy, W. Methyl alcohol II. Molecular structure. J. Chem. Phys. 23, 1200-1202 (1955).
19. Reisenauer, H. P., Romanski, J., Mloston, G. & Schreiner, P. R. Dimethoxycarbene: Conformational analysis of a reactive intermediate. Eur. J. Org. Chem. 4813-4818 (2006).
20. Sodeau, J. R. & Lee, E. K. C. Intermediacy of hydroxymethylene (HCOH) in the low temperature matrix photochemistry of formaldehyde. Chem. Phys. Lett. 57, 71-74 (1978).
21. Miller, W. H. Tunneling corrections to unimolecular rate constants, with application to formaldehyde. J. Am. Chem. Soc. 101, 6810-6814 (1979).
22. Miller, W. H., Handy, N. C. & Adams, J. E. Reaction path Hamiltonian for polyatomic molecules. J. Chem. Phys. 72, 99-112 (1980).
23. Carrington, T. Jr, Hubbard, L. M., Schaefer, H. F. & Miller, W. H. Vinylidene: Potential energy surface and unimolecular reaction dynamics. J. Chem. Phys. 80, 4347-4354 (1984).
24. Johnston, H. S. Gas Phase Reaction Rate Theory (Ronald Press, New York, 1966).
25. McMahon, R. J. & Chapman, O. L. Direct spectroscopic observation of intramolecular hydrogen shifts in carbenes. J. Am. Chem. Soc. 109, 683-692 (1987).
26. Zuev, P. S. & Sheridan, R. S. Tunneling in the C-H insertion of a singlet carbene: tert-Butylchlorocarbene. J. Am. Chem. Soc. 116, 4123-4124 (1994).
27. Pettersson, M. et al. Cis → trans conversion of formic acid by dissipative tunneling in solid rare gases: Influence of environment on the tunneling rate. J. Chem. Phys. 117, 9095-9098 (2002).
28. Maçôas, E. M. S., Khriachtchev, L., Pettersson, M., Fausto, R. & Räsänen, M. Rotational isomerism of acetic acid isolated in rare-gas matrices: Effect of medium and isotopic substitution on IR-induced isomerization quantum yield and cis → trans tunneling rate. J. Chem. Phys. 121, 1331-1338 (2004).
29. Zou, S., Bowman, J. M. & Brown, A. Full-dimensionality quantum calculations of acetylene-vinylidene isomerization. J. Chem. Phys. 118, 10012-10023 (2003).
30. Mátyus, E., Czakó, G., Sutcliffe, B. T. & Császár, A. G. Vibrational energy levels with arbitrary potentials using the Eckart-Watson Hamiltonians and the discrete variable representation. J. Chem. Phys. 127, 084102 (2007).
31. Allen, W. D., East, A. L. L. & Császár, A. G. in Structures and Conformations of Non-Rigid Molecules (eds Laane, J., Dakkouri, M., van der Veken, B. & Oberhammer, H.) 343-373 (NATO ASI Series C, Kluwer, Dordrecht, 1993).
32. Császár, A. G. et al. in Spectroscopy from Space (eds Demaison, J., Sarka, K. & Cohen, E. A.) 317-339 (NATO Science Series II, Vol. 20, Kluwer, Dordrecht, 2001).
33. Schuurman, M. S., Muir, S. R., Allen, W. D. & Schaefer, H. F. Toward subchemical accuracy in computational thermochemistry: Focal point analysis of the heat of formation of NCO and [H,N,C,O] isomers. J. Chem. Phys. 120, 11586-11599 (2004).
34. 2). Chem. Eur. J. 9, 2173-2192 (2003).
35. Dunning, T. H. Jr. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J. Chem. Phys. 90, 1007-1023 (1989).
36. Woon, D. E. & Dunning, T. H. Jr. Gaussian basis sets for use in correlated molecular calculations. V. Core-valence basis sets for boron through neon. J. Chem. Phys. 103, 4572-4585 (1995).
37. Perera, A. S. & Bartlett, R. J. Relativistic effects at the correlated level. An application to interhalogens. Chem. Phys. Lett. 216, 606-612 (1993).
38. Balasubramanian, K. Relativistic Effects in Chemistry Part A, Theory and Techniques (Wiley, New York, 1997).
39. Tarczay, G., Császár, A. G., Klopper, W. & Quiney, H. M. Anatomy of relativistic energy corrections in light molecular systems. Mol. Phys. 99, 1769-1794 (2001).
40. Bomble, Y. J., Stanton, J. F., Kállay, M. & Gauss, J. Coupled-cluster methods including noniterative corrections for quadruple excitations. J. Chem. Phys. 123, 054101 (2005).
41. Kállay, M. & Gauss, J. Approximate treatment of higher excitations in coupled-cluster theory. J. Chem. Phys. 123, 214105 (2005).
42. Evangelista, F. A., Allen, W. D. & Schaefer, H. F. High-order excitations in state-universal and state-specific multireference coupled cluster theories: Model systems. J. Chem. Phys. 125, 154113 (2006).
43. Watson, J. K. G. in Vibrational Spectra and Structure, Vol. 6 (ed. Durig, J. R.) 1-89 (Elsevier, New York and Amsterdam, 1977).
44. Mills, I. M. in Molecular Spectroscopy: Modern Research (eds Rao, K. N. & Mathews, C. W.) 1-115 (Academic, New York, 1972).
45. Papoušek, D. & Aliev, M. R. Molecular Vibrational- Rotational Spectra (Elsevier, Amsterdam, 1982).
46. Nielsen, H. H. The vibration-rotation energies of molecules. Rev. Mod. Phys. 23, 90-136 (1951).
47. Clabo, D. A. Jr, Allen, W. D., Remington, R. B., Yamaguchi, Y. & Schaefer, H. F. A systematic study of molecular vibrational anharmonicity and vibration-rotation interaction by self-consistent-field higher-derivative methods. Asymmetric top molecules. Chem. Phys. 123, 187-239 (1988).
48. Allen, W. D. et al. A systematic study of molecular vibrational anharmonicity and vibration-rotation interaction by self-consistent-field higher-derivative methods. Linear polyatomic molecules. Chem. Phys. 145, 427-466 (1990).
49. 3. J. Comput. Chem. 26, 1106-1112 (2005).
50. DeKock, R. L. et al. The electronic structure and vibrational spectrum of trans-HNOO. J. Phys. Chem. A 108, 2893-2903 (2004).
51. Czakó, G., Furtenbacher, T., Császár, A. G. & Szalay, V. Variational vibrational calculations using high-order anharmonic force fields. Mol. Phys. 102, 2411-2423 (2004).
52. Fukui, K. A formulation of the reaction coordinate. J. Phys. Chem. 74, 4161-4163 (1970).
53. Gonzales, C. & Schlegel, H. B. Reaction path following in mass-weighted internal coordinates. J. Phys. Chem. 94, 5523-5527 (1990).
54. Allen, W. D., Bodi, A., Szalay, V. & Császár, A. G. Adiabatic approximations to internal rotation. J. Chem. Phys. 124, 224310 (2006).
55. Liboff, R. L. Introductory Quantum Mechanics (Addison-Wesley, Reading, Massachusetts, 2003).
56. Razavy, M. Quantum Theory of Tunneling (World Scientific, Singapore, 2003).
57. Gray, S. K., Miller, W. H., Yamaguchi, Y. & Schaefer, H. F. Reaction path Hamiltonian: Tunneling effects in the unimolecular isomerization HNC → HCN. J. Chem. Phys. 73, 2733-2739 (1980).