Hydrogen-tunneling in biologically relevant small molecules: The rotamerizations of α-ketocarboxylic acids

Journal of Physical Chemistry B

Volumn 119, Issue 3, 2015, Pages 693-703

  Gerbig, Dennis ^a   Schreiner, Peter R ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

QUANTUM THEORY;

ARYL CARBOXYLIC ACIDS; BIOLOGICALLY RELEVANT SMALL MOLECULES; CONFORMATIONAL PREFERENCES; CRYOGENIC TEMPERATURES; KETOCARBOXYLIC ACIDS; PHENYLGLYOXYLIC ACID; PHOTO-IRRADIATION; QUANTUM-MECHANICAL TUNNELING;

HYDROGEN;

CARBOXYLIC ACID; HYDROGEN;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTRON; KINETICS; QUANTUM THEORY; STEREOISOMERISM;

CARBOXYLIC ACIDS; ELECTRONS; HYDROGEN; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; STEREOISOMERISM;

EID: 84921494249     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp503633m     Document Type: Article

References (77)

1. Terhorst, J. P.; Jorgensen, W. L. E / Z Energetics for Molecular Modeling and Design J. Chem. Theory Comput. 2010, 6, 2762-2769
2. Pettersson, M.; Lundell, J.; Khriachtchev, L.; Räsänen, M. IR Spectrum of the Other Rotamer of Formic Acid, Cis -HCOOH J. Am. Chem. Soc. 1997, 119, 11715-11716
3. Pettersson, M.; Maçôas, E. M. S.; Khriachtchev, L.; Lundell, J.; Fausto, R.; Räsänen, M. Cis → Trans Conversion of Formic Acid by Dissipative Tunneling in Solid Rare Gases: Influence of Environment on the Tunneling Rate J. Chem. Phys. 2002, 117, 9095-9098
4. Pettersson, M.; Maçôas, E. M. S.; Khriachtchev, L.; Fausto, R.; Räsänen, M. Conformational Isomerization of Formic Acid by Vibrational Excitation at Energies Below the Torsional Barrier J. Am. Chem. Soc. 2003, 125, 4058-4059
5. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Fausto, R.; Räsänen, M. Rotational Isomerism in Acetic Acid: The First Experimental Observation of the High-Energy Conformer J. Am. Chem. Soc. 2003, 125, 16188-16189
6. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Juselius, J.; Fausto, R.; Räsänen, M. Reactive Vibrational Excitation Spectroscopy of Formic Acid in Solid Argon: Quantum Yield for Infrared Induced Trans → Cis Isomerization and Solid State Effects on the Vibrational Spectrum J. Chem. Phys. 2003, 119, 11765-11772
7. Maçôas, E. M. S.; Khriachtchev, L.; Fausto, R.; Räsänen, M. Photochemistry and Vibrational Spectroscopy of the Trans and Cis Conformers of Acetic Acid in Solid Ar J. Phys. Chem. A 2004, 108, 3380-3389
8. 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. 2004, 121, 1331-1338
9. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Fausto, R.; Räsänen, M. Internal Rotation in Propionic Acid: Near-Infrared-Induced Isomerization in Solid Argon J. Phys. Chem. A 2005, 109, 3617-3625
10. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Fausto, R.; Räsänen, M. Rotational Isomerization of Small Carboxylic Acids Isolated in Argon Matrices: Tunnelling and Quantum Yields for the Photoinduced Processes Phys. Chem. Chem. Phys. 2005, 7, 743-749
11. Marushkevich, K.; Khriachtchev, L.; Räsänen, M. High-Energy Conformer of Formic Acid in Solid Neon: Giant Difference between the Proton Tunneling Rates of Cis Monomer and Trans-Cis Dimer J. Chem. Phys. 2007, 126, 241102
12. Marushkevich, K.; Khriachtchev, L.; Räsänen, M. High-Energy Conformer of Formic Acid in Solid Hydrogen: Conformational Change Promoted by Host Excitation Phys. Chem. Chem. Phys. 2007, 9, 5748-5751
13. Domanskaya, A.; Marushkevich, K.; Khriachtchev, L.; Räsänen, M. Spectroscopic Study of Cis -to- Trans Tunneling Reaction of HCOOD in Rare Gas Matrices J. Chem. Phys. 2009, 130, 154509
14. Marushkevich, K.; Räsänen, M.; Khriachtchev, L. Interaction of Formic Acid with Nitrogen: Stabilization of the Higher-Energy Conformer J. Phys. Chem. A 2010, 114, 10584-10589
15. Lopes, S.; Domanskaya, A. V.; Fausto, R.; Räsänen, M.; Khriachtchev, L. Formic and Acetic Acids in a Nitrogen Matrix: Enhanced Stability of the Higher-Energy Conformer J. Chem. Phys. 2010, 133, 144507
16. Marushkevich, K.; Siltanen, M.; Räsänen, M.; Halonen, L.; Khriachtchev, L. Identification of New Dimers of Formic Acid: The Use of a Continuous-Wave Optical Parametric Oscillator in Matrix Isolation Experiments J. Phys. Chem. Lett. 2011, 2, 695-699
17. 2 Complexes in Solid Argon: Stabilization of the Higher-Energy Conformer of Formic Acid J. Phys. Chem. A 2012, 116, 5305-5311
18. Lundell, J.; Räsänen, M.; Latajka, Z. Matrix Isolation FTIR and Ab Initio Study of Complexes between Formic Acid and Nitrogen Chem. Phys. 1994, 189, 245-260
19. Lundell, J.; Räsänen, M. Photochemistry of Formic Acid in Rare Gas Matrices: Double-Doping Experiments on the 193 nm Induced Photodecomposition J. Mol. Struct. 1997, 437, 349-358
20. Nishino, S.; Nakata, M. Intramolecular Hydrogen Atom Tunneling in 2-Chlorobenzoic Acid Studied by Low-Temperature Matrix-Isolation Infrared Spectroscopy J. Phys. Chem. A 2007, 111, 7041-7047
21. Maçôas, E. M. S.; Myllyperkiö, P.; Kunttu, H.; Pettersson, M. Vibrational Relaxation of Matrix-Isolated Carboxylic Acid Dimers and Monomers J. Phys. Chem. A 2009, 113, 7227-7234
22. Trakhtenberg, L. I.; Fokeyev, A. A.; Zyubin, A. S.; Mebel, A. M.; Lin, S. H. Matrix Reorganization with Intramolecular Tunneling of H Atom: Formic Acid in Ar Matrix J. Chem. Phys. 2009, 130, 144502
23. Amiri, S.; Reisenauer, H. P.; Schreiner, P. R. Electronic Effects on Atom Tunneling: Conformational Isomerization of Monomeric Para -Substituted Benzoic Acid Derivatives J. Am. Chem. Soc. 2010, 132, 15902-15904
24. Trakhtenberg, L. I.; Fokeyev, A. A.; Zyubin, A. S.; Mebel, A. M.; Lin, S. H. Effect of the Medium on Intramolecular H-Atom Tunneling: Cis-Trans Conversion of Formic Acid in Solid Matrixes of Noble Gases J. Phys. Chem. B 2010, 114, 17102-17112
25. Bazsó, G.; Góbi, S.; Tarczay, G. Near-Infrared Radiation Induced Conformational Change and Hydrogen Atom Tunneling of 2-Chloropropionic Acid in Low-Temperature Ar Matrix J. Phys. Chem. A 2012, 116, 4823-4832
26. Cao, Q.; Melavuori, M.; Lundell, J.; Räsänen, M.; Khriachtchev, L. Matrix-Isolation and Ab Initio Study of the Complex between Formic Acid and Xenon J. Mol. Struct. 2012, 1025, 132-139
27. Meyer, R.; Ha, T.-k.; Frei, H.; Günthard, H. Acetic Acid Monomer: Ab Initio Study, Barrier to Proton Tunnelling, and Infrared Assignment Chem. Phys. 1975, 9, 393-402
28. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Lundell, J.; Fausto, R.; Räsänen, M. Infrared-Induced Conformational Interconversion in Carboxylic Acids Isolated in Low-Temperature Rare-Gas Matrices Vib. Spectrosc. 2004, 34, 73-82
29. Maçôas, E. M. S.; Khriachtchev, L.; Pettersson, M.; Fausto, R.; Räsänen, M. Internal Rotation in Propionic Acid: Near-Infrared-Induced Isomerization in Solid Argon J. Phys. Chem. A 2005, 109, 3617-3625
30. Marushkevich, K.; Khriachtchev, L.; Lundell, J.; Räsänen, M. Cis-Trans Formic Acid Dimer: Experimental Observation and Improved Stability against Proton Tunneling J. Am. Chem. Soc. 2006, 128, 12060-12061
31. Isoniemi, E.; Khriachtchev, L.; Makkonen, M.; Räsänen, M. UV Photolysis Products of Propiolic Acid in Noble-Gas Solids J. Phys. Chem. A 2006, 110, 11479-11487
32. Marushkevich, K.; Khriachtchev, L.; Lundell, J.; Domanskaya, A.; Räsänen, M. Matrix Isolation and Ab Initio Study of Trans-Trans and Trans-Cis Dimers of Formic Acid J. Phys. Chem. A 2010, 114, 3495-3502
33. Marushkevich, K.; Khriachtchev, L.; Räsänen, M.; Melavuori, M.; Lundell, J. Dimers of the Higher-Energy Conformer of Formic Acid: Experimental Observation J. Phys. Chem. A 2012, 116, 2101-2108
34. Marushkevich, K.; Khriachtchev, L.; Lundell, J.; Domanskaya, A. V.; Räsänen, M. Vibrational Spectroscopy of Trans and Cis Deuterated Formic Acid (HCOOD): Anharmonic Calculations and Experiments in Argon and Neon Matrices J. Mol. Spectrosc. 2010, 259, 105-110
35. Fleury, G.; Tabacik, V. Acide Glyoxylique: Symétrie De La Molécule Libre, Spectres De Vibration Et Attribution J. Mol. Struct. 1971, 10, 359-372
36. Fleury, G.; Tabacik, V. Acide Glyoxylique: Symétrie De La Molécule Libre, Spectres De Vibration Et Attribution J. Mol. Struct. 1971, 10, 359-379 Erratum: J. Mol. Struct. 1972, 12, 156
37. Marstokk, K. M.; Møllendal, H. Microwave Spectrum, Conformation, Dipole Moment and Centrifugal Distortion of Glyoxylic Acid J. Mol. Struct. 1973, 15, 137-150
38. McMurry, J.; Begley, T. The Organic Chemistry of Biological Pathways, 1 st ed.; Roberts and Company Publishers: Greenwood Village, CO, 2005.
39. Bazsó, G.; Magyarfalvi, G.; Tarczay, G. Tunneling Lifetime of the ttc /VIp Conformer of Glycine in Low-Temperature Matrices J. Phys. Chem. A 2012, 116, 10539-10547
40. Najbauer, E. E.; Bazsó, G.; Góbi, S.; Magyarfalvi, G.; Tarczay, G. Exploring the Conformational Space of Cysteine by Matrix Isolation Spectroscopy Combined with Near-Infrared Laser Induced Conformational Change J. Phys. Chem. B 2014, 118, 2093-2103
41. Gerbig, D.; Reisenauer, H. P.; Wu, C.-H.; Ley, D.; Allen, W. D.; Schreiner, P. R. Phenylhydroxycarbene J. Am. Chem. Soc. 2010, 132, 7273-7275
42. Maçôas, E. M. S.; Lundell, J.; Pettersson, M.; Khriachtchev, L.; Fausto, R.; Räsänen, M. Vibrational Spectroscopy of Cis-and Trans -Formic Acid in Solid Argon J. Mol. Spectrosc. 2003, 219, 70-80
43. Ley, D.; Gerbig, D.; Wagner, J. P.; Reisenauer, H. P.; Schreiner, P. R. Cyclopropylhydroxycarbene J. Am. Chem. Soc. 2011, 133, 13614-13621
44. Cremer, D. Møller-Plesset Perturbation Theory: From Small Molecule Methods to Methods for Thousands of Atoms Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1, 509-530
45. Fukui, K. A Formulation of the Reaction Coordinate J. Phys. Chem. 1970, 74, 4161-4163
46. Fukui, K. The Path of Chemical Reactions Acc. Chem. Res. 1981, 14, 363-368
47. Hratchian, H. P.; Schlegel, H. B. Accurate Reaction Paths Using a Hessian Based Predictor-Corrector Integrator J. Chem. Phys. 2004, 120, 9918-9924
48. Hratchian, H. P. Using Efficient Predictor-Corrector Reaction Path Integrators for Studies Involving Projected Frequencies J. Chem. Theory Comput. 2012, 8, 5013-5019
49. Hratchian, H. P.; Kraka, E. Improved Predictor-Corrector Integrators for Evaluating Reaction Path Curvature J. Chem. Theory Comput. 2013, 9, 1481-1488
50. Becke, A. D. Density-Functional Exchange-Energy: Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38, 3098-3100
51. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
52. Perdew, J. P. Density-Functional Approximation for the Correlation Energy of the Inhomogeneous Electron Gas Phys. Rev. B 1986, 33, 8822-8824
53. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
54. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1997, 78, 1396
55. Perdew, J. P.; Burke, K.; Wang, Y. Generalized Gradient Approximation for the Exchange-Correlation Hole of a Many-Electron System Phys. Rev. B 1996, 54, 16533-16539
56. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Atoms, Molecules, Solids, and Surfaces: Applications of the Generalized Gradient Approximation for Exchange and Correlation Phys. Rev. B 1992, 46, 6671-6687
57. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Erratum: Atoms, Molecules, Solids, and Surfaces: Applications of the Generalized Gradient Approximation for Exchange and Correlation Phys. Rev. B 1993, 48, 4978
58. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167
59. Zhao, Y.; Truhlar, D. G. Exploring the Limit of Accuracy of the Global Hybrid Meta Density Functional for Main-Group Thermochemistry, Kinetics, and Noncovalent Interactions J. Chem. Theory Comput. 2008, 4, 1849-1868
60. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06 Functionals and Twelve Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
61. Baboul, A. G.; Schlegel, H. B. Improved Method for Calculating Projected Frequencies Along a Reaction Path J. Chem. Phys. 1997, 107, 9413-9417
62. Čížek, J. On the Correlation Problem in Atomic and Molecular Systems. Calculation of Wavefunction Components in Ursell-Type Expansion Using Quantum-Field Theoretical Methods J. Chem. Phys. 1966, 45, 4256-4266
63. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. A Fifth-Order Perturbation Comparison of Electron Correlation Theories Chem. Phys. Lett. 1989, 157, 479-483
64. Bartlett, R. J.; Watts, J. D.; Kucharski, S. A.; Noga, J. Non-Iterative Fifth-Order Triple and Quadruple Excitation Energy Corrections in Correlated Methods Chem. Phys. Lett. 1990, 165, 513-522
65. Stanton, J. F. Why CCSD(T) Works: A Different Perspective Chem. Phys. Lett. 1997, 281, 130-134
66. 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. Gaussian09, revision D.01. Gaussian Inc.: Wallingford, CT, 2013.
67. Neese, F. The Orca Program System Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 73-78
68. Kiselev, V. G.; Swinnen, S.; Nguyen, V. S.; Gritsan, N. P.; Nguyen, M. T. Fast Reactions of Hydroxycarbenes: Tunneling Effect Versus Bimolecular Processes J. Phys. Chem. A 2010, 114, 5573-5579
69. Gerbig, D.; Ley, D.; Reisenauer, H. P.; Schreiner, P. R. Intramolecular Hydroxycarbene C-H-Insertion: The Curious Case of (o -Methoxyphenyl)hydroxycarbene Beilstein J. Org. Chem. 2010, 6, 1061-1069
70. Gerbig, D.; Ley, D.; Schreiner, P. R. Light- and Heavy-Atom Tunneling in Rearrangement Reactions of Cyclopropylcarbenes Org. Lett. 2011, 13, 3526-3529
71. Mathematica 9.0; Wolfram Research, Inc.: Champaign, IL, 2013, (http://www.wolfram.com).
72. Olbert-Majkut, A.; Lundell, J.; Wierzejewska, M. Light-Induced Opening and Closing of the Intramolecular Hydrogen Bond in Glyoxylic Acid J. Phys. Chem. A 2014, 118, 350-357
73. Reva, I. D.; Stepanian, S. G.; Adamowicz, L.; Fausto, R. Combined FTIR Matrix Isolation and Ab Initio Studies of Pyruvic Acid: Proof for Existence of the Second Conformer J. Phys. Chem. A 2001, 105, 4773-4780
74. Lundell, J.; Olbert-Majkut, A. Isolated Glyoxylic Acid-Water 1:1 Complexes in Low Temperature Argon Matrices. Spectrochim. Acta, Part A 2013, in press (http://dx.doi.org/10.1016/j.saa.2013.1008.1120).
75. Khriachtchev, L.; Maçôas, E.; Pettersson, M.; Räsänen, M. Conformational Memory in Photodissociation of Formic Acid J. Am. Chem. Soc. 2002, 124, 10994-10995
76. Schreiner, P. R.; Reisenauer, H. P.; Ley, D.; Gerbig, D.; Wu, C.-H.; Allen, W. D. Methylhydroxycarbene: Tunneling Control of a Chemical Reaction Science 2011, 332, 1300-1303
77. Ley, D.; Gerbig, D.; Schreiner, P. R. Tunnelling Control of Chemical Reactions: The Organic Chemist's Perspective Org. Biomol. Chem. 2012, 10, 3781-3790