Spectroscopic and structural investigation of 2,5-dicarboxy-1- methylpyridinium inner salt

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 121, Issue , 2014, Pages 586-595

  Barczynski P ^a   Komasa, A ^a   Katrusiak, A ^a   Dega Szafran, Z ^a   Nowaczyk, Ł ^a   Ratajczak Sitarz, M ^a   Szafran, M ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

2,5 Dicarboxy 1 methylpyridinium inner salt; DFT calculations; FTIR and NMR spectra; Hydrogen bonds; X ray diffraction

Indexed keywords

ABSORPTION SPECTROSCOPY; CARBOXYLATION; DIMERS; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTIMIZATION; TITRATION; VOLTAMMETRY; X RAY DIFFRACTION;

CARBOXYLATE GROUPS; DFT CALCULATION; FTIR AND NMR SPECTRA; ISOTROPIC SHIELDING; NEIGHBORING MOLECULES; NMR CHEMICAL SHIFTS; POTENTIOMETRIC TITRATIONS; STRUCTURAL INVESTIGATION;

HYDROGEN BONDS;

1 METHYLPYRIDINIUM; 1-METHYLPYRIDINIUM; DRUG DERIVATIVE; NICOTINIC ACID; PYRIDINIUM DERIVATIVE;

2,5-DICARBOXY-1-METHYLPYRIDINIUM INNER SALT; ARTICLE; CHEMISTRY; CONFORMATION; DFT CALCULATIONS; FTIR AND NMR SPECTRA; HYDROGEN BOND; HYDROGEN BONDS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAMAN SPECTROMETRY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

2,5-DICARBOXY-1-METHYLPYRIDINIUM INNER SALT; DFT CALCULATIONS; FTIR AND NMR SPECTRA; HYDROGEN BONDS; X-RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; NIACIN; PYRIDINIUM COMPOUNDS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS, RAMAN; THERMODYNAMICS;

EID: 84888222756     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2013.10.123     Document Type: Article

References (77)

1. Y. Song, B. Yan, and Z. Chen J. Coord. Chem. 58 2005 811 816
2. H.-L. Gao, C. Cheng, B. Ding, W. Shi, H.-B. Song, P. Cheng, D.-Z. Liao, S.-P. Yan, and Z.-H. Jiang J. Mol. Struct. 738 2005 105 111
3. Y. Wei, H. Hou, L. Li, Y. Fan, and Y. Zhu Cryst. Growth Des. 5 2005 1405 1413
4. S. Yan, X. Li, and X. Zheng J. Mol. Struct. 929 2009 105 111
5. A.T. Çolak, O.Z. Yeşilel, and O. Büyükgü ngör J. Mol. Struct. 991 2011 68 72
6. H. Nishitani, K. Nishitsuji, K. Okumura, and H. Taguchi Phytochemistry 42 1996 1 6
7. H. Taguchi, M. Maeda, H. Nishitani, K. Okumura, Y. Shimabayashi, and K. Iwai Biosci. Biotech. Biochem. 56 1992 1921 1923
8. H. Taguchi, A. Kashimoto, H. Nishitani, Y. Shimabayashi, and K. Iwai Agric. Biol. Chem. 52 1988 85 89
9. P. Sengupta, S. Ghosh, and T.C.W. Mak Polyhedron 20 2001 975 980
10. R.I. Dowell, and E.M. Hadley J. Med. Chem. 35 1992 800 804
11. H. Tucker, and D.F. Thomas J. Med. Chem. 35 1992 804 807
12. J.S. Lee, H.S. Shim, Y.K. Park, Y.S. Shin, W.Y. Yang, H.D. Lee, W.J. Park, Y.H. Chung, and S.W. Lee Bioorg. Med. Chem. Lett. 12 2002 2715 2717
13. M.R. Silva, P.S.P. Silva, A.M. Beja, J.A. Paixão, L.L.G. Justino, and A.J.F.N. Sobral J. Mol. Struct. 837 2007 58 62
14. D.C. Coomber, D.J. Tucker, and A.M. Bond Analyst 122 1997 1587 1591
15. F.M. Menger, A.L. Galloway, and D. Lundberg J. Am. Chem. Soc. 127 2005 1915 11914 11915
16. J. Wang, G.-W. Li, Y.-C. Lin, S.-N. Zhou, and S.W. Ng Acta Cryst. E 61 2005 o1515 o1516
17. A.T. Çolak, F. Çolak, D. Akduman, O.Z. Yeşilel, and O. Büyükgüngör Solid State Sci. 11 2009 1908 1918
18. A.T. Çolak, O.Z. Yeşilel, and O. Büyükgü ngör Polyhedron 29 2010 2127 2133
19. A.T. Çolak, O.Z. Yeşilel, G. Pamuk, H. Günay, and O. Büyükgüngör Polyhedron 30 2011 1012 1022
20. J. Jin, X. Han, Q. Meng, D. Li, Y.-X. Chi, and S.-Y. Niu J. Solid State Chem. 197 2013 92 102
21. A.C. Wibowo, M.D. Smith, and H.-C. zur Loye Solid State Sci. 13 2011 607 615
22. A.C. Wibowo, S.A. Vaughn, M.D. Smith, and H.-C. zur Loye Inorg. Chem. 49 2010 11001 11008
23. A.C. Wibowo, M.D. Smith, and H.-C. zur Loye Chem. Commun. 47 2011 7371 7373
24. A.C. Wibowo, M.D. Smith, and H.-C. zur Loye Cryst. Growth Des. 11 2011 4449 4457
25. G.M. Rakić, S. Grgurić-Šipka, G.N. Kalucrossed d signerović, M. Bette, L. Filipović, S. Arancrossed d signelović, S. Radulović, and Ž.Lj. Tešić Eur. J. Med. Chem. 55 2012 214 219
26. N. Ma, T. Zhang, and G.-R. Yang Acta Cryst. E68 2012 m41 m42
27. Y.-G. Huang, X.-T. Wang, F.-L. Jiang, S. Gao, M.-Y. Wu, Q Gao, W. Wei, and M.-C. Hong Chem. Eur. J. 14 2008 10340 10347
28. H. Kumagai, and H. Sobukawa J. Mater. Sci. 43 2008 2123 2130
29. C. Qin, X.-L. Wang, E.-B. Wang, and Z.-M. Su Inorg. Chem. 44 2005 7122 7129
30. C. Yang, J. Wang, W. Wang, and W. Zhan J. Solid State Chem. 184 2011 2485 2489
31. A. Schmidt Adv. Heterocycl. Chem. 85 2003 67 171
32. E. Alcaide Adv. Heterocycl. Chem. 60 1994 197 259
33. J.A. Zoltewicz, and L.W. Deady Adv. Heterocycl. Chem. 22 1978 71 121
34. X-B. Wang, J.E. Dacres, X. Yang, K.M. Broadus, L. Lis, L-S. Wang, and S.R. Kass J. Am. Chem. Soc 125 2003 296 304
35. E.E. Smissman, and G. Hite J. Am. Chem. Soc. 81 1959 1201 1203
36. E.M. Kosower, and J.W. Patton J. Org. Chem. 26 1961 1318 1319
37. R.E. Phillips, and R.L. Soulen J. Chem. Educ. 72 1995 624 625
38. P. Barczyński, A. Katrusiak, J. Koput, and M. Szafran J. Mol. Struct. 889 2008 394 401
39. P. Barczyński, M. Szafran, M. Ratajczak-Sitarz, Ł. Nowaczyk, Z. Dega-Szafran, and A. Katrusiak J. Mol. Struct. 1018 2012 21 27
40. P. Barczyński, M. Ratajczak-Sitarz, Ł. Nowaczyk, A. Katrusiak, Z. Dega-Szafran, and M. Szafran J. Mol. Struct. 1013 2012 1 10
41. M.L. Peterson J. Org. Chem. 25 1960 565 569
42. G.M. Sheldrick Acta Crystallogr. A 64 2008 112 122
43. C.K. Johnson, ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976.
44. Stereochemical Workstation Operation Manual, Release 3.4, Siemens Analytical X-ray Instruments INC. Madison, 1989.
45. 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, and J.A. Pople GAUSSIAN 03. Revision B.05 2003 Gaussian, Inc. Pittsburgh, PA
46. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
47. A.D. Becke J. Chem. Phys. 107 1997 8554 8580
48. C. Lee, W. Yang, and C.R. Parr Phys. Rev. B 37 1988 785 789
49. W.J. Hehre, L. Random, P.V.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1989 Wiley New York
50. V. Barone, and M. Cossi J. Phys. Chem. A 102 1998 1995 2001
51. G. Brancato, N. Rega, and V. Barone J. Chem. Phys. 125 2006 164515 164525
52. A. Klamt COSMO-RS. From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design 2005 Elsevier Amsterdam
53. K. Wolinski, J.F. Hinton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260 (and ref. cited therein)
54. E. Norkus, E. Gaidamauskas, I. Stalnioniene, and D.C. Crans Heteroatom Chem. 16 2005 285 291
55. C. Petitfaux, and R. Fournaise Bull. Soc. Chim. France 1972 914 926
56. A. Novak Struct. Bond. 18 1974 177 214
57. J. Baran, M. Drozd, T. Głowiak, M. Śledź, and H. Ratajczak J. Mol. Struct. 372 1995 131 144
58. P. Barczyński, A. Komasa, M. Ratajczak-Sitarz, A. Katrusiak, Z. Dega-Szafran, and M. Szafran J. Mol. Struct. 994 2011 216 222
59. J. Emsley Chem. Soc. Revs. 9 1980 91 124
60. G. Talsky Derivative Spectrophotometry 1994 Wiley-VCH Weinheim, Germany
61. M. Szafran, Z. Dega-Szafran, M. Jaskólski, A. Addlagatta, and E. Dulewicz J. Mol. Struct. 741 2005 171 181
62. L.B. Jerzykiewicz, Z. Malarski, L. Sobczyk, T. Lis, and E. Grech J. Mol. Struct. 440 1998 175 185
63. A.E. Frisch, R.D. Dennington, T.A. Keith, A.B. Neilsen, and A.J. Holder Gauss View 3.0.9 2003 Gaussian Inc. Pittsburg, PA
64. P. Scott, and L. Radom J. Phys. Chem. 100 1996 16502 16513
65. M. Alcolea Palafox Int. J. Quant. Chem. 77 2000 661 684
66. M. Alcolea Palafox, and V.K. Rastogi Spectrochim. Acta A 58 2002 411 440
67. K. Szczepaniak, M.M. Szcześniak, and W.B. Person J. Phys. Chem. A 104 2000 3852 3863
68. K. Szczepaniak, W.B. Person, and D. Hadži J. Phys. Chem. A 109 2005 6710 6724
69. M. Alcolea Palafox, M. Gill, N.J. Nunez, V.K. Rastogi, L. Mittal, and R. Sharma Int. J. Quant. Chem. 103 2005 394 421
70. Y.I. Binev, M.K. Georgieva, and L.I. Daskalova Spectrochim. Acta A 60 2004 2601 2610
71. F. Fretsch, P. Bühlman, and C. Affolter Structure Determination of Organic Compounds, Tables of Spectral Data 2000 Springer-Verlag Berlin
72. P.M. Tolstoy, P. Schah-Mohammedi, S.N. Smirnov, N.S. Golubev, G.S. Denisov, and H.-H. Limbach J. Am. Chem. Soc. 126 2004 5621 5634
73. P.M. Tolstoy, J. Guo, B. Koeppe, N.S. Golubev, G.S. Denisov, S.N. Smirnov, and H.-H. Limbach J. Phys. Chem. A 114 2010 10775 10782
74. J. Guo, P.M. Tolstoy, B. Koeppe, N.S. Golubev, G.S. Denisov, S.N. Smirnov, and H.-H. Limbach J. Phys. Chem. A 116 2012 11180 11188
75. A. Forsyth, and A.B. Sebag J. Am. Chem. Soc. 119 1997 9483 9494
76. B. Ośmiałowski, E. Kolehmainen, and R. Gawinecki Magn. Res. Chem. 39 2001 334 340 (and references cited therein)
77. A. Katrusiak J. Mol. Graph. Model. 19 2001 363 367