Structure, vibrational spectra and DFT characterization of the intra- and inter-molecular interactions in 2-hydroxy-5-methylpyridine-3-carboxylic acid - Normal modes of the eight-membered HB ring

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 120, Issue , 2014, Pages 304-313

  Godlewska, P ^a   Janczak J ^b   Kucharska, E ^a   Hanuza, J ^a,b   Lorenc, J ^a   Michalski, J ^a   Dyminska L ^a   Weglinski Z ^a  

^a WROCLAW UNIVERSITY OF ECONOMICS   (Poland)

^b INSTITUTE OF LOW TEMPERATURE AND STRUCTURE RESEARCH   (Poland)

Author keywords

DFT; Dimer; HB ring; Hydrogen bridge; Vibrational spectra; X ray

Indexed keywords

CARBOXYLIC ACIDS; DIMERS; MOLECULAR STRUCTURE; QUANTUM CHEMISTRY; SOFTWARE PACKAGES; VIBRATIONAL SPECTRA; X RAYS;

CRYSTALLOGRAPHIC PLANE; DFT; GEOMETRY OPTIMIZATION; HYDROGEN BRIDGES; INTERMOLECULAR INTERACTIONS; IR AND RAMAN SPECTRA; QUANTUM CHEMICAL CALCULATIONS; VIBRATIONAL PROPERTIES;

HYDROGEN BONDS;

CARBOXYLIC ACID; DIMER; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DFT; DIMERIZATION; HB RING; HYDROGEN BOND; HYDROGEN BRIDGE; METHYLATION; QUANTUM THEORY; VIBRATIONAL SPECTRA; X RAY CRYSTALLOGRAPHY; X-RAY;

DFT; DIMER; HB RING; HYDROGEN BRIDGE; VIBRATIONAL SPECTRA; X-RAY;

CARBOXYLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; HYDROGEN BONDING; METHYLATION; MODELS, MOLECULAR; PYRIDINES; QUANTUM THEORY;

EID: 84886733772     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2013.09.130     Document Type: Article

References (48)

1. W. Brzyska, and W. Ozga Pol. J. Chem. 71 1997 436 440
2. D.C. Crans, L. Yang, T. Jakusch, and T. Kiss Inorg. Chem. 39 2000 4409 4416
3. M.J.O. Neil The Merck Index 13th ed. 2001 Merck & Co. Whitehouse Station, New Jersey
4. S. Ferraro, P. Passamonti, V. Bartocci, and F. Pucciarelli J. Chem. Soc. Faraday Trans. 93 1997 289 294
5. B.D. Dawis, R. Dulbecco, H.N. Eisen, H.S. Ginsberg, and W.B. Wood Microbiology second ed. 1973 Herper & Row Hagerstown
6. E. Norkus, I. Stalnioniene, and D.C. Crans Heteroat. Chem. 14 2003 625 632 and references therein
7. D.C. Crans J. Inorg. Biochem. 80 2000 123 131
8. L.Q. Yang, D.C. Crans, S.M. Miller, A. la Cour, O.P. Anderson, P.M. Kaszynski, M.E. Godzala, L.D. Austin, and G.R. Willsky Inorg. Chem. 41 2002 4859 4871
9. Z. Wȩgliński, and T. Talik Ann. Soc. Chim. Polonorum 51 1977 2401 2409
10. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision A.1, Gaussian Inc., Pittsburgh PA, 2003.
11. A.D. Becke J. Chem. Phys. 104 1996 1040 1046
12. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B37 1988 785 789
13. M.A. Palafox, and V.K. Rastogi Spectrochim. Acta A 58 2002 411 440
14. M.J. Nowak, L. Lapinski, BALGA computer program for PED calculations; H. Rostkowska, L. Lapinski, M.J. Nowak; Vibr. Spectrosc. 49 (2009) 43-51).
15. M.M. Szczesniak, D. Maślanka, Animol-computer Program, Infrared and Raman Spectroscopy Teaching and Research Tool, Version 3.2.1., 1995-1997.
16. P. Pulay, G. Fogarasi, F. Pang, and J.E. Boggs J. Am. Chem. Soc. 101 10 1979 2550 2560
17. G. Fogarasi, X. Zhou, P.W. Taylor, and P. Pulay J. Am. Chem. Soc. 114 1992 8191
18. E.D. E.D. Glengening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1, TCI, University of Visconsin, Madison, 1998.
19. Kuma Diffraction, KM-4 CCD Software. Version 171.23 (2004), Kuma Diffraction, Wrocław, Poland, 2004.
20. G.M. Sheldrick Acta Cryst. A46 1990 467 473
21. G.M. Sheldrick, SHELXS97 and SHELXL97 (1997), Program for the Solution and Refinement of Crystal Structures. University of Göttingen, Germany, 1997.
22. R.J. Gillespie Chem. Soc. Rev. 21 1992 59 69
23. F.H. Allen Acta Cryst. B58 2002 380 388
24. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Tailor J. Chem. Soc. Perkin Trans. 2 1987 S1 S19
25. K.B. Wilberg, V.A. Walters, K.N. Wong, and S.D. Colson J. Phys. Chem. 88 1984 6067 6075
26. F. Partal Urena, M. Fernandez Gomez, J.J. Lopez Gonzales, and E. Martinez Torres Spectrochim. Acta A 59 2003 2815 2839
27. G.A. Babu, P. Ramasamy, and J. Philip Mater. Res. Bull. 46 2011 631 634
28. E. Kucharska, W. Sa̧siadek, J. Janczak, H. Ban-Oganowska, J. Lorenc, Z. Wȩgliński, Z. Talik, K. Hermanowicz, and J. Hanuza Vib. Spec. 53 2010 189 198
29. M. Wandas, E. Kucharska, J. Michalski, Z. Talik, J. Lorenc, and J. Hanuza J. Mol. Struct. 1004 2011 156 162
30. J. Lorenc, I. Bryndal, M. Marchewka, W. Sa̧siadek, T. Lis, and J. Hanuza J. Raman Spectrosc. 39 2008 569 581
31. E. Kucharska, J. Hanuza, M. Ma̧czka, and Z. Talik Vib. Spectrosc. 39 2005 1 14
32. G. Socrates Infrared Raman Characteristic Group Frequencies 2001 Wiley and Sons Ltd. and references therein
33. D. Lin-vien, N.B. Cothup, W.G. Fateley, and J.G. Graselli The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules 1991 Academic Press Boston
34. J. Michalski, J. Hanuza, M. Ma̧czka, Z. Talik, T. Głowiak, A. Szemik-Hojniak, and J.H. Van der Maas J. Mol. Struct. 596 2001 109 121
35. M. Diem Introduction to Modern Vibrational Spectroscopy 1993 Wiley New York
36. E. Fan, C. Vincent, S.J. Geib, and A.D. Hamilton Chem. Mater. 6 1994 1113 1117
37. O. Ermer, and A. Eling J. Chem. Soc. Perkin Trans. 2 1994 925 944
38. S. Coe, J.J. Kane, T.L. Nguyen, L.M. Toledo, E. Wininger, F.F. Fowler, and J.W. Laugher J. Am. Chem. Soc. 119 1997 86 93
39. G.T.R. Palmore, and M.T. McBride Chem. Commun. 1998 145 146
40. Y. Ducharme, and J.D. Wuest J. Org. Chem. 53 1988 5787 5789
41. M. Simard, D. Su, and J.D. Wuest J. Am. Chem. Soc. 113 1991 4696 4698
42. C.B. Aakeröy, A.M. Beatty, M. Nieuwenhuyzen, and M. Zou Tetrahedron 56 2000 6693 6699
43. J. Lorenc, J. Bryndal, W. Syska, M. Wandas, M. Marchewka, A. Pietraszko, T. Lis, M. Ma̧czka, K. Hermanowicz, and J. Hanuza Chem. Phys. 374 2010 1 14
44. Z. Li, J. Huang, and A. Meng J. Chem. Crystallogr. 41 2011 481 484
45. L. Leiserowitz Acta Crystallogr. B32 1976 775 802
46. M.C. Etter, J.C. McDonald, and J. Bernstein Acta Crystallogr. B46 1990 256 262
47. A.F. Reed, L.A. Curtiss, and J. Weinhold Chem. Rev. 88 1988 899
48. I. Bryndal, E. Kucharska, W. Sa̧siadek, M. Wandas, T. Lis, J. Lorenc, and J. Hanuza Spectrochim. Acta A 96 2012 952 962