Reaction pathways by quantum Monte Carlo: Insight on the torsion barrier of 1,3-butadiene, and the conrotatory ring opening of cyclobutene

BARBORINI, Matteo; Guidoni, Leonardo

doi:10.1063/1.4769791

Article (Scientific journals)

Reaction pathways by quantum Monte Carlo: Insight on the torsion barrier of 1,3-butadiene, and the conrotatory ring opening of cyclobutene

BARBORINI, Matteo; Guidoni, Leonardo

2012 • In Journal of Chemical Physics, 137 (22)

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https://hdl.handle.net/10993/65322

DOI
10.1063/1.4769791

PubMed
23249005

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Keywords :

Ground state geometry; Intramolecular reactions; Quantum monte carlo; Quantum Monte Carlo methods; Reaction barriers; Reaction pathways; Transition state geometry; Variational Monte Carlo; Physics and Astronomy (all); Physical and Theoretical Chemistry

Abstract :

[en] Quantum Monte Carlo (QMC) methods are used to investigate the intramolecular reaction pathways of 1,3-butadiene. The ground state geometries of the three conformers s-trans, s-cis, and gauche, as well as the cyclobutene structure are fully optimised at the variational Monte Carlo (VMC) level, obtaining an excellent agreement with the experimental results and other quantum chemistry high level calculations. Transition state geometries are also estimated at the VMC level for the s-trans to gauche torsion barrier of 1,3-butadiene and for the conrotatory ring opening of cyclobutene to the gauche-1,3-butadiene conformer. The energies of the conformers and the reaction barriers are calculated at both variational and diffusional Monte Carlo levels providing a precise picture of the potential energy surface of 1,3-butadiene and supporting one of the two model profiles recently obtained by Raman spectroscopy [Boopalachandran, J. Phys. Chem. A 115, 8920 (2011)10.1021/ jp2051596]. Considering the good scaling of QMC techniques with the system's size, our results also demonstrate how variational Monte Carlo calculations can be applied in the future to properly investigate the reaction pathways of large and correlated molecular systems. © 2012 American Institute of Physics.

Disciplines :

Chemistry

Author, co-author :

BARBORINI, Matteo ; University of Luxembourg > Faculty of Science, Technology and Medicine (FSTM) > HPC Platform ; Dipartimento di Matematica Pura Ed Applicata, Università Degli Studi dell'Aquila, 67100 L'Aquila, Italy ; Dipartimento di Scienze Fisiche e Chimiche, Università Degli Studi dell'Aquila, 67100 L'Aquila, Italy

Guidoni, Leonardo; Dipartimento di Matematica Pura Ed Applicata, Università Degli Studi dell'Aquila, 67100 L'Aquila, Italy

External co-authors :

yes

Language :

English

Title :

Reaction pathways by quantum Monte Carlo: Insight on the torsion barrier of 1,3-butadiene, and the conrotatory ring opening of cyclobutene

Publication date :

14 December 2012

Journal title :

Journal of Chemical Physics

ISSN :

0021-9606

eISSN :

1089-7690

Publisher :

American Institute of Physics Inc.

Volume :

137

Issue :

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://pubs.aip.org/aip/jcp/article-pdf/doi/10.1063/1.4769791/13999406/224309_1_online.pdf

Funding text :

The authors thank Professor Sandro Sorella for the development of the TURBORVB quantum Monte Carlo code, and Dr. Emanuele Coccia for the implementation of harmonic constraints in the code and for the accurate revision of this article. The authors acknowledge funding provided by the European Research Council (Project No. 240624) within the VII Framework Program of the European Union. For the availability of high performance computing resources and support we acknowledge the CINECA Award IscrB_QMC-BLA-2011, the PRACE Tier-0 Project PRA053, and the Caliban HPC center of the University of L'Aquila.

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Bibliography

R. B. Scott, R. D. Rands Jr., C. H. Meyers, F. G. Brickwedde, and N. Bekkedahl, J. Res. Natl. Bur. Stand. 35, 39 (1945). 10.6028/jres.035.017
J. G. Aston, G. Szasz, H. W. Woolley, and F. G. Brickwedde, J. Chem. Phys. 14, 67 (1946). 10.1063/1.1724108
A. Almenningen, O. Bastiansen, and M. Traetteberg, Acta Chem. Scand. 12, 1221 (1958). 10.3891/acta.chem.scand.12-1221
W. Haugen and M. Traetteberg, Acta Chem. Scand. 20, 1726 (1966). 10.3891/acta.chem.scand.20-1726
K. Kuchisu, T. Fukuyama, and Y. Morino, J. Mol. Struct. 1, 463 (1968). 10.1016/0022-2860(68)87020-6
N. C. Craig, P. Groner, and D. C. McKean, J. Phys. Chem. A 110, 7461 (2006). 10.1021/jp060695b
M. E. Squillacote, R. S. Sheridan, O. L. Chapman, and F. A. L. Anet, J. Am. Chem. Soc. 101, 3657 (1979). 10.1021/ja00507a042
J. J. Fisher and J. Michl, J. Am. Chem. Soc. 109, 1056 (1987). 10.1021/ja00238a012
B. R. Arnold, V. Balaji, and J. Michl, J. Am. Chem. Soc. 112, 1808 (1990). 10.1021/ja00161a025
B. R. Arnold, V. Balaji, J. W. Downing, J. G. Radziszewski, J. J. Fisher, and J. Michl, J. Am. Chem. Soc. 113, 2910 (1991). 10.1021/ja00008a019
C. H. Choi, M. Kertesz, S. Dobrin, and J. Michl, Theor. Chem. Acc. 102, 196 (1999). 10.1007/s002140050491
K. B. Wiberg and R. E. Rosenberg, J. Am. Chem. Soc. 112, 1509 (1990). 10.1021/ja00160a033
R. L. Lipnick and E. W. Garbisch, J. Am. Chem. Soc. 95, 6370 (1973). 10.1021/ja00800a034
L. Radom and J. A. Pople, J. Am. Chem. Soc. 92, 4786 (1970). 10.1021/ja00719a005
U. Pincelli, B. Cadioli, and B. Lévy, Chem. Phys. Lett. 13, 249 (1972). 10.1016/0009-2614(72)85053-X
P. Skancke and J. E. Boggs, J. Mol. Struct. 16, 179 (1973). 10.1016/0022-2860(73)80060-2
B. Dumbacher, Theor. Chem. Acc. 23, 346 (1972). 10.1007/BF00526440
S. Skaarup, J. Boggs, and P. Skancke, Tetrahedron 32, 1179 (1976). 10.1016/0040-4020(76)85042-9
C. W. Bock, P. George, and M. Trachtman, Theor. Chem. Acc. 64, 293 (1984). 10.1007/BF00551014
M. A. Murcko, H. Castejon, and K. B. Wiberg, J. Phys. Chem. 100, 16162 (1996). 10.1021/jp9621742
X. Gong and H. Xiao, Int. J. Quantum Chem. 69, 659 (1998). 10.1002/(SICI)1097-461X(1998)69:5<659::AID-QUA4>3.0.CO;2-U
J. C. Sancho-García, A. J. Pérez-Jiménez, J. M. Pérez-Jordá, and F. Moscardó, Mol. Phys. 99, 47 (2001). 10.1080/00268970109483487
Y. N. Panchenko, J. V. Auwera, Y. Moussaoui, and G. R. De Maré, Struct. Chem. 14, 337 (2003). 10.1023/A:1024445810013
C. S. Page and M. Olivucci, J. Comput. Chem. 24, 298 (2003). 10.1002/jcc.10145
S. Saha, F. Wang, C. T. Falzon, and M. J. Brunger, J. Chem. Phys. 123, 124315 (2005). 10.1063/1.2034467
M. Boggio-Pasqua, M. J. Bearpark, M. Klene, and M. A. Robb, J. Chem. Phys. 120, 7849 (2004). 10.1063/1.1690756
A. Karpfen and V. Parasuk, Mol. Phys. 102, 819 (2004). 10.1080/00268970410001726863
D. C. McKean, N. C. Craig, and Y. N. Panchenko, J. Phys. Chem. A 110, 8044 (2006). 10.1021/jp060566v
D. Feller and N. C. Craig, J. Phys. Chem. A 113, 1601 (2009). 10.1021/jp8095709
R. Engeln, D. Consalvo, and J. Reuss, Chem. Phys. 160, 427 (1992). 10.1016/0301-0104(92)80010-S
P. Boopalachandran, N. Craig, P. Groner, and J. Laane, J. Phys. Chem. A 115, 8920 (2011). 10.1021/jp2051596
W. Cooper and W. D. Walters, J. Am. Chem. Soc. 80, 4220 (1958). 10.1021/ja01549a025
W. P. Hauser and W. D. Walters, J. Phys. Chem. 67, 1328 (1963). 10.1021/j100800a039
R. W. Carr and W. D. Walters, J. Phys. Chem. 69, 1073 (1965). 10.1021/j100887a510
K. B. Wiberg and R. A. Fenoglio, J. Am. Chem. Soc. 90, 3395 (1968). 10.1021/ja01015a018
D. C. Spellmeyer and K. N. Houk, J. Am. Chem. Soc. 110, 3412 (1988). 10.1021/ja00219a012
M. A. McAllister and T. T. Tidwell, J. Am. Chem. Soc. 116, 7233 (1994). 10.1021/ja00095a028
J. Baker, M. Muir, and J. Andzelm, J. Chem. Phys. 102, 2063 (1995). 10.1063/1.468728
P. Celani, F. Bernardi, M. Olivucci, and M. A. Robb, J. Chem. Phys. 102, 5733 (1995). 10.1063/1.469304
O. Wiest, D. C. Montiel, and K. N. Houk, J. Phys. Chem. A 101, 8378 (1997). 10.1021/jp9717610
L. Deng and T. Ziegler, J. Phys. Chem. 99, 612 (1995). 10.1021/j100002a025
P. K. Chattaraj, P. Fuentealba, B. Gómez, and R. Contreras, J. Am. Chem. Soc. 122, 348 (2000). 10.1021/ja992337a
P. Deng, L.-C. Li, A.-M. Tian, and N.-B. Wong, Int. J. Quantum Chem. 100, 288 (2004). 10.1002/qua.20159
L. Guidoni and U. Rothlisberger, J. Chem. Theory Comput. 1, 554 (2005). 10.1021/ct050081v
M. Jaccob, I. Sheeba Jem, S. Giri, P. Venuvanalingam, and P. K. Chattaraj, J. Phys. Org. Chem. 24, 460 (2011). 10.1002/poc.1785
E. Coccia and L. Guidoni, J. Comput. Chem. 33, 2332 (2012). 10.1002/jcc.23071
S. Sorella and S. Capriotti, J. Chem. Phys. 133, 234111 (2010). 10.1063/1.3516208
M. Barborini, S. Sorella, and L. Guidoni, J. Chem. Theory Comput. 8, 1260 (2012). 10.1021/ct200724q
O. Valsson, C. Angeli, and C. Filippi, Phys. Chem. Chem. Phys. 14, 11015 (2012). 10.1039/C2CP41387F
E. Coccia, D. Varsano, and L. Guidoni, " Protein field effect on the dark state of 11-cis retinal in rhodopsin by quantum Monte Carlo/molecular mechanics.," J. Chem. Theory Comput. (published online). 10.1021/ct3007502
J. C. Grossman, W. A. Lester, and S. G. Louie, J. Am. Chem. Soc. 122, 705 (2000). 10.1021/ja983879f
C. Filippi, S. B. Healy, P. Kratzer, E. Pehlke, and M. Scheffler, Phys. Rev. Lett. 89, 166102 (2002). 10.1103/PhysRevLett.89.166102
A. C. Kollias, O. Couronne, and J. W. A. Lester, J. Chem. Phys. 121, 1357 (2004). 10.1063/1.1756863
A. Zen, D. Zhelyazov, and L. Guidoni, J. Chem. Theory Comput. 8, 4204 (2012). 10.1021/ct300576n
L. K. Wagner and J. C. Grossman, Phys. Rev. Lett. 104, 210201 (2010). 10.1103/PhysRevLett.104.210201
S. Sorella, M. Casula, and D. Rocca, J. Chem. Phys. 127, 14105 (2007). 10.1063/1.2746035
G. Mazzola, A. Zen, and S. Sorella, J. Chem. Phys. 137, 134112 (2012). 10.1063/1.4755992
C. J. Umrigar, Int. J. Quantum Chem. 36, 217 (1989). 10.1002/qua. 560360826
R. Assaraf and M. Caffarel, J. Chem. Phys. 119, 10536 (2003). 10.1063/1.1621615
O. Valsson and C. Filippi, J. Chem. Theory Comput. 6, 1275 (2010). 10.1021/ct900692y
C. Attaccalite and S. Sorella, Phys. Rev. Lett. 100, 114501 (2008). 10.1103/PhysRevLett.100.114501
M. Casula, C. Filippi, and S. Sorella, Phys. Rev. Lett. 95, 100201 (2005). 10.1103/PhysRevLett.95.100201
M. Casula, S. Moroni, S. Sorella, and C. Filippi, J. Chem. Phys. 135, 154113 (2010). 10.1063/1.3653229
M. Casula and S. Sorella, J. Chem. Phys. 119, 6500 (2003). 10.1063/1.1604379
L. Pauling, The Nature of the Chemical Bond, 3rd ed. (Cornell University Press, Itaca, New York, 1960), pp. 230-240.
J. A. Pople, Proc. R. Soc. London, Ser. A 202, 323 (1950). 10.1098/rspa.1950.0103
M. Casula, M. Marchi, S. Azadi, and S. Sorella, Chem. Phys. Lett. 477, 255 (2009). 10.1016/j.cplett.2009.07.005
F. Sterpone, L. Spanu, L. Ferraro, S. Sorella, and L. Guidoni, J. Chem. Theory Comput. 4, 1428 (2008). 10.1021/ct800121e
E. Coccia, O. Chernomor, M. Barborini, S. Sorella, and L. Guidoni, J. Chem. Theory Comput. 8, 1952 (2012). 10.1021/ct300171q
M. Marchi, S. Azadi, C. Casula, and S. Sorella, J. Chem. Phys. 131, 154116 (2009). 10.1063/1.3249966
N. D. Drummond, M. D. Towler, and R. J. Needs, Phys. Rev. B 70, 235119 (2004). 10.1103/PhysRevB.70.235119
S. Sorella, TURBORVB quantum Monte Carlo package, see http://people.sissa.it/~sorella/web/index.html.
M. Burkatzki, C. Filippi, and M. Dolg, J. Chem. Phys. 126, 234105 (2007). 10.1063/1.2741534
J. R. Trail and R. J. Needs, J. Chem. Phys. 122, 174109 (2005). 10.1063/1.1888569
K. Kveseth, R. Seip, and D. A. Kohl, Acta Chem. Scand., Ser. A 34, 31 (1980). 10.3891/acta.chem.scand.34a-0031
W. Caminati, G. Grassi, and A. Bauder, Chem. Phys. Lett. 148, 13 (1988). 10.1016/0009-2614(88)87251-8
T. H. Dunning, J. Chem. Phys. 90, 1007 (1989). 10.1063/1.456153
J. Saltiel, D. F. Sears, and A. M. Turek, J. Phys. Chem. A 105, 7569 (2001). 10.1021/jp011493c
B. Bak, J. Led, L. Nygaard, J. Rastrup-Andersen, and G. Sorensen, J. Mol. Struct. 3, 369 (1969). 10.1016/0022-2860(69)87033-X
M. Olivucci, I. N. Ragazos, F. Bernardi, and M. A. Robb, J. Am. Chem. Soc. 115, 3710 (1993). 10.1021/ja00062a042