Tetrazole acetic acid: Tautomers, conformers, and isomerization

Journal of Chemical Physics

Volumn 140, Issue 6, 2014, Pages

  Araujo Andrade, C ^a,b   Reva, I ^b   Fausto, R ^b  

^a UNIVERSIDAD AUTÓNOMA DE ZACATECAS   (Mexico)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ATOMS; CONFORMATIONS; HIGH ENERGY FORMING; INFRARED DEVICES; INFRARED SPECTROSCOPY; IRRADIATION; ISOMERS; MONOMERS; PH; POTENTIAL ENERGY; QUANTUM CHEMISTRY; SUBLIMATION;

CRYSTALLINE COMPOUNDS; ISOLATED MONOMERS; PROTON TUNNELING; RELATIVE ENERGIES; REVERSE TRANSFORMATION; SUBLIMATION TEMPERATURE; TAUTOMERIZATION PROCESS; VIBRATIONAL CALCULATIONS;

LINEAR TRANSFORMATIONS;

EID: 84907222809     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.4864119     Document Type: Article

References (77)

1. R. Haiges and K. O. Christe, Inorg. Chem. 52, 7249 (2013). 10.1021/ic400919n
2. T. Mavromoustakos, A. Kolocouris, M. Zervou, P. Roumelioti, J. Matsoukas, and R. Weisemann, J. Med. Chem. 42, 1714 (1999). 10.1021/jm980499w
3. K. Noda, Y. Saad, A. Kinoshita, T. P. Boyle, R. M. Graham, A. Husain, and S. S. Karnik, J. Biol. Chem. 270, 2284 (1995). 10.1074/jbc.270.5.2284
4. A. De Sarro, D. Ammendola, M. Zappala, S. Grasso, and G. B. De Sarro, Antimicrob. Agents Chemother. 39, 232 (1995). 10.1128/AAC.39.1.232
5. I. Alkorta and J. Elguero, Struct. Chem. 16, 507 (2005). 10.1007/s11224-005-4550-x
6. V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, and O. V. Denisko, Adv. Heterocycl. Chem. 76, 157 (2000). 10.1016/S0065-2725(00)76005-3
7. J. Elguero, " The tautomerism of heterocycles," Advances in Heterocyclic Chemistry (Academic Press Inc., 1976), 682 pp.
8. G. Rauhut, in Advances in Heterocyclic Chemistry, edited by A. R. Katritzky (Elsevier Academic Press Inc, San Diego, 2001), vol. 81, p. 1.
9. A. El Hammadi and M. El Mouhtadi, J. Mol. Struct.: THEOCHEM 497, 241 (2000). 10.1016/S0166-1280(99)00380-2
10. G. S. Li, M. F. Ruiz-López, M. S. Zhang, and B. Maigret, J. Mol. Struct.: THEOCHEM 422, 197 (1998). 10.1016/S0166-1280(97)00095-X
11. J. Catalán, J. L. G. de Paz, and J. Elguero, J. Chem. Soc., Perkin Trans. 2 1996, 57. 10.1039/p29960000057
12. F. Tomas, J. L. M. Abboud, J. Laynez, R. Notario, L. Santos, S. O. Nilsson, J. Catalán, R. M. Claramunt, and J. Elguero, J. Am. Chem. Soc. 111, 7348 (1989). 10.1021/ja00201a011
13. M. Pagacz-Kostrzewa, I. D. Reva, R. Bronisz, B. M. Giuliano, R. Fausto, and M. Wierzejewska, J. Phys. Chem. A 115, 5693 (2011). 10.1021/jp202925r
14. V. G. Kiselev, P. B. Cheblakov, and N. P. Gritsan, J. Phys. Chem. A 115, 1743 (2011). 10.1021/jp112374t
15. R. E. Trifonov, I. Alkorta, V. A. Ostrovskii, and J. Elguero, J. Mol. Struct.: THEOCHEM 668, 123 (2004). 10.1016/j.theochem.2003.10.019
16. A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano, and R. Fausto, J. Phys. Chem. A 109, 7967 (2005). 10.1021/jp0517706
17. A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano, and R. Fausto, J. Mol. Struct. 786, 182 (2006). 10.1016/j.molstruc.2005.08.019
18. L. M. T. Frija, I. V. Khmelinskii, C. Serpa, I. D. Reva, R. Fausto, and M. L. S. Cristiano, Org. Biomol. Chem. 6, 1046 (2008). 10.1039/b718104c
19. L. M. T. Frija, M. L. S. Cristiano, A. Gómez-Zavaglia, I. Reva, and R. Fausto, J. Photochem. Photobiol. C: Photochem. Rev. 18, 71 (2014). 10.1016/j.jphotochemrev.2013.09.001
20. A. Ismael, M. L. S. Cristiano, R. Fausto, and A. Gomez-Zavaglia, J. Phys. Chem. A 114, 13076 (2010). 10.1021/jp109215q
21. L. M. T. Frija, I. Reva, A. Ismael, D. V. Coelho, R. Fausto, and M. L. S. Cristiano, Org. Biomol. Chem. 9, 6040 (2011). 10.1039/c1ob05460k
22. S. C. S. Bugalho, L. Lapinski, M. L. S. Cristiano, L. M. T. Frija, and R. Fausto, Vib. Spectrosc. 30, 213 (2002). 10.1016/S0924-2031(02)00028-0
23. R. Goddard, O. Heinemann, and C. Krüger, Acta Crystallogr., Sect. C 53, 590 (1997). 10.1107/S0108270197000772
24. W. C. McCrone, D. Grabar, and E. Lieber, Anal. Chem. 23, 543 (1951). 10.1021/ac60051a052
25. C. Zhaoxu and X. Heming, J. Mol. Struct.: THEOCHEM 453, 65 (1998). 10.1016/S0166-1280(98)00177-8
26. R. N. Butler, V. C. Garvin, H. Lumbroso, and C. Liégeois, J. Chem. Soc., Perkin Trans. 2 1984, 721. 10.1039/p29840000721
27. A. P. Mazurek and N. Sadlej-Sosnowska, Chem. Phys. Lett. 330, 212 (2000). 10.1016/S0009-2614(00)01060-5
28. B. S. Jursic and Z. Zdravkovski, J. Mol. Struct.: THEOCHEM 337, 9 (1995). 10.1016/0166-1280(94)04116-A
29. S. C. S. Bugalho, E. M. S. Maçôas, M. L. S. Cristiano, and R. Fausto, Phys. Chem. Chem. Phys. 3, 3541 (2001). 10.1039/b103344c
30. P. T. Chou, C. Y. Wei, C. P. Chang, and C. H. Chiu, J. Am. Chem. Soc. 117, 7259 (1995). 10.1021/ja00132a032
31. K. C. Ingham, M. Abu-Elgheit, and M. A. El-Bayoumi, J. Am. Chem. Soc. 93, 5023 (1971). 10.1021/ja00749a007
32. K. C. Ingham and M. A. El-Bayoumi, J. Am. Chem. Soc. 96, 1674 (1974). 10.1021/ja00813a006
33. K. Tokumura, Y. Watanabe, M. Udagawa, and M. Itoh, J. Am. Chem. Soc. 109, 1346 (1987). 10.1021/ja00239a010
34. K. Fuke and K. Kaya, J. Phys. Chem. 93, 614 (1989). 10.1021/j100339a023
35. M. Negrerie, F. Gai, S. M. Bellefeuille, and J. W. Petrich, J. Phys. Chem. 95, 8663 (1991). 10.1021/j100175a046
36. Z. B. Yang and M. T. Rodgers, Phys. Chem. Chem. Phys. 6, 2749 (2004). 10.1039/b315089e
37. J. E. Combariza, B. Just, J. Manz, and G. K. Paramonov, J. Phys. Chem. 95, 10351 (1991). 10.1021/j100178a022
38. M. Pagacz-Kostrzewa, D. Jesariew, M. Podruczna, and M. Wierzejewska, Spectrochim. Acta A 108, 229 (2013). 10.1016/j.saa.2013.01.086
39. L. Lapinski, I. Reva, H. Rostkowska, A. Halasa, R. Fausto, and M. J. Nowak, J. Phys. Chem. A 117, 5251 (2013). 10.1021/jp402128g
40. C. M. Nunes, L. Lapinski, R. Fausto, and I. Reva, J. Chem. Phys. 138, 125101 (2013). 10.1063/1.4795823
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
42. A. Andrzejewska, L. Lapinski, I. Reva, and R. Fausto, Phys. Chem. Chem. Phys. 4, 3289 (2002). 10.1039/b203240f
43. C. Araujo-Andrade, A. Gómez-Zavaglia, I. D. Reva, and R. Fausto, J. Phys. Chem. A 116, 2352 (2012). 10.1021/jp212169b
44. S. Breda, I. Reva, and R. Fausto, Vib. Spectrosc. 50, 57 (2009). 10.1016/j.vibspec.2008.07.015
45. A. J. Lopes Jesus, M. T. S. Rosado, I. Reva, R. Fausto, M. E. Eusébio, and J. S. Redinha, J. Phys. Chem. A 110, 4169 (2006). 10.1021/jp0572737
46. A. Sharma, I. Reva, and R. Fausto, J. Am. Chem. Soc. 131, 8752 (2009). 10.1021/ja903211f
47. I. Reva, B. J. A. N. Almeida, L. Lapinski, and R. Fausto, J. Mol. Struct. 1025, 74 (2012). 10.1016/j.molstruc.2011.11.051
48. G. Bazsó, E. E. Najbauer, G. Magyarfalvi, and G. Tarczay, J. Phys. Chem. A 117, 1952 (2013). 10.1021/jp400196b
49. S. G. Stepanian, I. D. Reva, E. D. Radchenko, and L. Adamowicz, J. Phys. Chem. A 102, 4623 (1998). 10.1021/jp973479z
50. G. A. Zhurko, Chemcraft, 1.6., 2012, see http://www.chemcraftprog.com.
51. R. E. Trifonov and V. A. Ostrovskii, Russ. J. Org. Chem. 42, 1585 (2006). 10.1134/S1070428006110017
52. M. T. S. Rosado, A. J. Lopes Jesus, I. D. Reva, R. Fausto, and J. S. Redinha, J. Phys. Chem. A 113, 7499 (2009). 10.1021/jp900771g
53. I. D. Reva, A. J. Lopes Jesus, M. T. S. Rosado, R. Fausto, M. E. Eusébio, and J. S. Redinha, Phys. Chem. Chem. Phys. 8, 5339 (2006). 10.1039/b610962d
54. S. G. Stepanian, I. D. Reva, E. D. Radchenko, M. T. S. Rosado, M. L. T. S. Duarte, R. Fausto, and L. Adamowicz, J. Phys. Chem. A 102, 1041 (1998). 10.1021/jp973397a
55. M. T. Rosado, M. L. T. S. Duarte, and R. Fausto, Phosphorus Sulfur Silicon 116, 153 (1996). 10.1080/10426509608040477
56. E. M. S. Macaas, L. Khriachtchev, M. Pettersson, R. Fausto, and M. Räsänen, J. Phys. Chem. A 109, 3617 (2005).
57. A. Sharma, I. Reva, R. Fausto, S. Hesse, Z. Xue, M. A. Suhm, S. K. Nayak, R. Sathishkumar, R. Pal, and T. N. Guru Row, J. Am. Chem. Soc. 133, 20194 (2011). 10.1021/ja2030646
58. I. Reva, L. Lapinski, and R. Fausto, J. Mol. Struct. 976, 333 (2010). 10.1016/j.molstruc.2010.03.081
59. I. Reva, A. Simão, and R. Fausto, Chem. Phys. Lett. 406, 126 (2005). 10.1016/j.cplett.2005.02.067
60. I. Reva, M. J. Nowak, L. Lapinski, and R. Fausto, J. Chem. Phys. 136, 064511 (2012). 10.1063/1.3683217
61. L. Lapinski, M. J. Nowak, I. Reva, H. Rostkowska, and R. Fausto, Phys. Chem. Chem. Phys. 12, 9615 (2010). 10.1039/c0cp00177e
62. S. Lopes, A. V. Domanskaya, R. Fausto, M. Räsänen, and L. Khriachtchev, J. Chem. Phys. 133, 144507 (2010).
63. N. Kus, A. Sharma, I. Peña, M. C. Bermúdez, C. Cabezas, J. L. Alonso, and R. Fausto, J. Chem. Phys. 138, 144305 (2013). 10.1063/1.4799456
64. E. M. S. Maç̂as, L. Khriachtchev, M. Pettersson, R. Fausto, and M. Räsänen, J. Am. Chem. Soc. 125, 16188 (2003).
65. M. Pettersson, E. M. S. Maç̂as, L. Khriachtchev, J. Lundell, R. Fausto, and M. Räsänen, J. Chem. Phys. 117, 9095 (2002).
66. E. M. S. Maç̂as, L. Khriachtchev, M. Pettersson, R. Fausto, and M. Räsänen, J. Chem. Phys. 121, 1331 (2004).
67. G. Bazsó, G. Magyarfalvi, and G. Tarczay, J. Phys. Chem. A 116, 10539 (2012). 10.1021/jp3076436
68. G. Bazsó, S. Gobi, and G. Tarczay, J. Phys. Chem. A 116, 4823 (2012). 10.1021/jp212597y
69. S. Amiri, H. P. Reisenauer, and P. R. Schreiner, J. Am. Chem. Soc. 132, 15902 (2010). 10.1021/ja107531y
70. S. Nishino and M. Nakata, J. Phys. Chem. A 111, 7041 (2007). 10.1021/jp0717600
71. I. D. Reva, S. G. Stepanian, L. Adamowicz, and R. Fausto, J. Phys. Chem. A 105, 4773 (2001). 10.1021/jp0101458
72. I. D. Reva, S. Jarmelo, L. Lapinski, and R. Fausto, J. Phys. Chem. A 108, 6982 (2004). 10.1021/jp0483627
73. I. D. Reva, S. Jarmelo, L. Lapinski, and R. Fausto, Chem. Phys. Lett. 389, 68 (2004). 10.1016/j.cplett.2004.03.062
74. I. D. Reva, A. M. Plokhotnichenko, S. G. Stepanian, A. Yu. Ivanov, E. D. Radchenko, G. G. Sheina, and Yu. P. Blagoi, Chem. Phys. Lett. 232, 141 (1995). 10.1016/0009-2614(95)90630-B
75. I. D. Reva, A. M. Plokhotnichenko, S. G. Stepanian, A. Yu. Ivanov, E. D. Radchenko, G. G. Sheina, and Yu. P. Blagoi, Chem. Phys. Lett. 235, 617 (1995). 10.1016/0009-2614(95)00190-F
76. L. Duarte, B. M. Giuliano, I. Reva, and R. Fausto, J. Phys. Chem. A 117, 10671 (2013). 10.1021/jp405061b
77. 2 matrix, recorded at 13 K before and after of annealing up to 24 K; Table S1 presenting internal coordinates used in the normal mode analysis of 1ccc and 1cct conformers of 1 H -TAA; Table S2 presenting internal coordinates used in the normal mode analysis of 2pcc and 2pct conformers of 2 H -TAA; Tables S3-S6 presenting B3LYP/6-311++G(d,p) calculated wavenumbers, absolute intensities, and potential energy distributions for the conformers 1ccc and 1cct of 1 H -TAA, as well as 2pcc and 2pct conformers of 2 H -TAA; Tables S7-S9 presenting Cartesian coordinates for the geometries of conformers of 1 H-and 2 H-tautomers of TAA optimized at the B3LYP, MP2, and QCISD levels with the 6-311++G(d,p) basis set.