First-principles study of salicylideneaniline molecular crystals: Tautomerization reaction involving intermolecular hydrogen bonds

Physical Review B - Condensed Matter and Materials Physics

Volumn 69, Issue 13, 2004, Pages

  Mikami, Masayoshi ^a   Nakamura, Shinichiro ^a  

^a MITSUBISHI CHEMICAL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; SALICYLALDEHYDE; SALICYLIDENEANILINE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTRICITY; HYDROGEN BOND; REFRACTION INDEX; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 42749099753     PISSN: 01631829     EISSN: None     Source Type: Journal    
DOI: 10.1103/PhysRevB.69.134205     Document Type: Article

References (44)

1. Molecular Electronics: Science and Technology, edited by A. Aviram and M. Ratner (The New York Academy of Sciences, New York, 1998).
2. M. Irie, Chem. Rev. (Washington, D.C.).100, 1685 (2000).
3. T. Fukaminato, S. Kobatake, T. Kawai, and M. Irie, Proc. Jpn. Acad., Ser. B: Phys. Biol. Sci. 77, 30 (2001).
4. Organic Photochromic and Thermochromic Compounds, edited by J.C. Crano and R.J. Guglielmetti (Plenum Press, New York, 1999).
5. Molecular Switches, edited by B.L. Feringa (Wiley-VCH, Weinheim, 2001).
6. M. Irie, S. Kobatake, and M. Horichi, Science 291, 1769 (2001).
7. J. Harada, H. Uekusa, and Y. Ohashi, J. Am. Chem. Soc. 121, 5809 (1999).
8. T. Kawato, H. Koyama, H. Kanatomi, and M. Isshiki, J. Photochem. 28, 103 (1985).
9. K. Ogawa, J. Harada, T. Fujiwara, and S. Yoshida, J. Phys. Chem. A 105, 3425 (2001).
10. K. Ogawa, J. Harada, I. Tamura, and Y. Noda, Chem. Lett. 29, 528 (2000).
11. K. Ogawa, Y. Kasahara, Y. Ohtani, and J. Harada, J. Am. Chem. Soc. 120, 7107 (1998).
12. I. Frank, D. Marx, and M. Parrinello, J. Phys. Chem. A 103, 7341 (1999).
13. S. Baroni, S. de Gironcoli, A. DalCorso, and P. Giannozzi, Rev. Mod. Phys. 73, 515 (2001), see also references therein.
14. M. Mikami, S. Nakamura, M. Itoh, K. Nakajima, and T. Shishido, Phys. Rev. B 65, 094302 (2002).
15. M. Mikami, S. Nakamura, O. Kitao, and H. Arakawa, Phys. Rev. B 66, 155213 (2002).
16. M. Mikami, S. Nakamura, M. Itoh, K. Nakajima, and T. Shishido, J. Lumin. 102-103, 7 (2003).
17. The ABINIT code (URL: http://www.abinit.org/) is a common project of the Université Catholique de Louvain, Coming Incorporated, the Université de Liège, the Commissariat à l'Energie Atomique, Mitsubishi Chemical Corporation and other contributors.
18. X. Gonze et al., Comput. Mater. Sci. 25, 478 (2002).
19. M. Payne, M. Teter, D. Allan, T. Arias, and I. Ioannopoulos, Rev. Mod. Phys. 64, 1045 (1992).
20. X. Gonze, Phys. Rev. B 54, 4383 (1996).
21. J.P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett. 77, 3865 (1996).
22. W. Koch and M.C. Holthausen, A Chemist's Guide to Density Functional Theory, 2nd ed. (Wiley-VCH, Weinheim, 2001).
23. D.R. Hamann, Phys. Rev. B 55, R10157 (1997).
24. N. Troullier and J.L. Martins, Phys. Rev. B 43, 1993 (1991).
25. H. Monkhorst and J. Pack, Phys. Rev. B 13, 5188 (1976).
26. 3, R =0.045, and GOF=1.129. Note that the occupancy of the trans-keto molecule was converged to 0.104 (2).
27. W.H. Press, S.A. Teukolsky, W.T. Vetterling, and B.P. Flannery, Numerical Recipes in Fortran: The Art of Scientific Computing, 2nd ed. (Cambridge University Press, Cambridge, 1992).
28. X. Gonze, Phys. Rev. B 55, 10 337 (1997).
29. X. Gonze and C. Lee, Phys. Rev. B 55, 10 355 (1997).
30. The calculations were performed at B3LYP/6-31G** level using GAUSSIAN98 package. GAUSSIAN98, Revision A.7, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C, Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople (Gaussian, Pittsburgh, PA, 1998).
31. K. Ogawa and T. Fujiwara, Chem. Lett. 28, 657 (1999).
32. 3) have also been calculated; the NH-form molecule is less stable than the OH-form molecule by 13.2 kcal/mol. We notice that the energy difference between the one-molecular case of the OH (NH) form and the corresponding isolated molecule in the cubic unit cell is about 2.4 kcal/mol (1.2 kcal/mol), respectively. This slight difference, which almost appears the order of the "chemical accuracy" (Ref. 22), may come from the effect of the limited size of the cubic cells. Due to the limitation of our compuational resource for larger supercells and the inability for van der Waals interaction in the present exchange-correlation functional, the reliable estimation of the cohesive energies was beyond our present study; the cohesive energies have not been experimentally known, either. Thus the present authors focus on the intermolecular interaction by comparison between twice the energy for one-molecular case and the energy of two-molecular case, expecting the same conditions of the k-point sampling of the Brillouin zone as well as the cancellation of the van der Waals interactions between the two forms.
33. M.Z. Zgierski and A. Grabowska, J. Chem. Phys. 112, 6329 (2000).
34. J. Bernstein, Polymorphism in Molecular Crystals (Oxford University Press, Oxford, 2002).
35. A. Kokalj, J. Mol. Graphics Modell. 17, 176 (1999); A. Kokalj, Comput. Mater. Sci. 28, 155 (2003).
36. A. Kokalj, J. Mol. Graphics Modell. 17, 176 (1999); A. Kokalj, Comput. Mater. Sci. 28, 155 (2003).
37. 60 face-centered cubic (fcc) solid greatly depends on the choice of k point for one-point samplings of the Brillouin zone; 4.72 for (1/2, 1/2, 1/2) while 5.64 for Γ point within local density approximation. It should be noted that the point (1/2, 1/2, 1/2) is the special k point of fcc cells for the one-point sampling (Ref. 42). Experimental evaluation of the dielectric constant is reported as 4.4 in Ref. 43.
38. From the present GAUSSIAN98 calculation, the HOMO-LUMO gap of the enol form is 0.128 18 a.u., while that of the trans-keto form is 0.10061 a.u.
39. Y. Zhang and Z.-H. Lu, Mater. Chem. Phys. 63, 188 (2000).
40. T. Kawai, N. Fukuda, D. Gröschl, S. Kobatake, and M. Irie, Jpn. J. Appl. Phys., Part 2 38, L1194 (1999).
41. J. Chauvin, T. Kawai, and M. Irie, Jpn. J. Appl. Phys., Part 1 40, 2518 (2001).
42. M. J. Weber, Handbook of Optical Materials (CRC Press, Boca Raton, 2003).
43. D.J. Chadi and M.L. Cohen, Phys. Rev. B 8, 5747 (1973).
44. A.F. Hebard, R.C. Haddon, R.M. Fleming, and A.R. Kortan, Appl. Phys. Lett. 59, 2109 (1991).