Structure and conformation of 2, 3-diethoxycarbonyl-1-methylpyridinium iodide studied by NMR, FTiR, Raman, X-ray diffraction and DFT methods

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 115, Issue , 2013, Pages 208-218

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

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

2,3 Diethoxycarbonyl 1 methylpyridinium; B3LYP 6 311G(d; Electrostatic Interactions; FTiR Raman and NMR spectra; Hydrogen bonds; Iodide; P) calculations; X ray diffraction

Indexed keywords

COMPLEXATION; COMPUTATION THEORY; COULOMB INTERACTIONS; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

2,3-DIETHOXYCARBONYL-1-METHYLPYRIDINIUM; IODIDE; ISOTROPIC SHIELDING; MOLECULAR GEOMETRIES; POSITIVELY CHARGED; RAMAN AND NMR SPECTRUM; SOLVATION MODELS; SPECTROSCOPIC PROPERTY;

CRYSTAL STRUCTURE;

1 METHYLPYRIDINIUM; 1-METHYLPYRIDINIUM; 2,3 DIETHOXYCARBONYL 1 METHYLPYRIDINIUM IODIDE; 2,3-DIETHOXYCARBONYL-1-METHYLPYRIDINIUM IODIDE; ANION; PYRIDINIUM DERIVATIVE;

ARTICLE; B3LYP/6-311G(D,P) CALCULATIONS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; ELECTROSTATIC INTERACTIONS; FTIR RAMAN AND NMR SPECTRA; HYDROGEN BONDS; INFRARED SPECTROSCOPY; MECHANICAL TORSION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; RAMAN SPECTROMETRY; THERMODYNAMICS; X RAY DIFFRACTION;

2,3-DIETHOXYCARBONYL-1-METHYLPYRIDINIUM IODIDE; B3LYP/6-311G(D,P) CALCULATIONS; ELECTROSTATIC INTERACTIONS; FTIR RAMAN AND NMR SPECTRA; HYDROGEN BONDS; X-RAY DIFFRACTION;

ANIONS; CRYSTALLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRIDINIUM COMPOUNDS; QUANTUM THEORY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS, RAMAN; THERMODYNAMICS; TORSION, MECHANICAL; X-RAY DIFFRACTION;

EID: 84880182766     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2013.05.046     Document Type: Article

References (46)

1. M. Szafran, A. Katrusiak, J. Koput, Z. Dega-Szafran, J. Mol. Struct. 846 (2007) 1-12.
2. M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, J. Mol. Struct. 700 (2004) 109-125.
3. M. Szafran, A. Katrusiak, Z. Dega-Szafran, J. Mol. Struct. 827 (2007) 56-66.
4. M. Szafran, A. Katrusiak, Z. Dega-Szafran, J. Mol. Struct. 839 (2007) 99-106.
5. M. Szafran, J. Koput, Z. Dega-Szafran, M. Pankowski, J. Mol. Struct. 614 (2002) 97-108.
6. M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, M. Pankowski, K. Stobiecka, Chem. Phys. 289 (2003) 201-219.
7. M. Szafran, A. Katrusiak, J. Koput, Z. Dega-Szafran, J. Mol. Struct. 784 (2006) 98-108.
8. M. Szafran, A. Katrusiak, J. Koput, Z. Dega-Szafran, J. Mol. Struct. 704 (2004) 45-52.
9. M. Szafran, E. Bartoszak-Adamska, J. Koput, Z. Dega-Szafran, J. Mol. Struct. 844-845 (2007) 140-158.
10. M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, J. Mol. Struct. 797 (2006) 66-81.
11. M. Szafran, A. Katrusiak, Z. Dega-Szafran, J. Mol. Struct. 794 (2006) 46-53.
12. M. Szafran, A. Katrusiak, Z. Dega-Szafran, J. Mol. Struct. 880 (2008) 77-85.
13. P. Barczyński, A. Komasa, M. Ratajczak-Sitarz, A. Katrusiak, Z. Dega-Szafran, M. Szafran, J. Mol. Struct. 994 (2011) 216-222.
14. M. Szafran, A. Katrusiak, Z. Dega-Szafran, P. Barczyński, J. Mol. Struct. 934 (2009) 79-85.
15. P. Barczyński, M. Ratajczak-Sitarz, Ł. Nowaczyk, A. Katrusiak, Z. Dega-Szafran, M. Szafran, J. Mol. Struct. 1013 (2012) 1-10.
16. P. Barczyński, M. Szafran, M. Ratajczak-Sitarz, Ł. Nowaczyk, Z. Dega-Szafran, A. Katrusiak, J. Mol. Struct. 1018 (2012) 21-27.
17. P. Barczyński, M. Ratajczak-Sitarz, Ł. Nowaczyk, A. Katrusiak, Z. Dega-Szafran, M. Szafran, J. Mol. Struct. 1035 (2013) 348-357.
18. G.M. Sheldrick, Acta Crystallogr. A64 (2008) 112-122.
19. C.K. Johnson, ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, Berlin, 1976.
20. Stereochemical Workstation Operation Manual, Release 3.4, Siemens Analytical X-ray instruments INC. Madison, 1989.
21. 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 B.05, Gaussian, Inc., Pittsburgh PA, 2003.
22. A.D. Becke, J. Chem. Phys 107 (1997) 8554-8580 (and ref. cited therein).
23. C. Lee, W. Yang, C.R. Part, Phys. Rev. B 37 (1988) 785-789.
24. W.J. Hehre, L. Random, P.V.R. Schleyer, J.A. Pople, Abinitio Molecular Orbital Theory, Wiley, New York, 1989.
25. D. Feller, J. Comp. Chem. 17 (1996) 1571-1586.
26. K.L. Schuchardt, B.T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, T.L. Windus, J. Chem. inf. Model 47 (2007) 1045-1052.
27. M.N. Glukhovtsev, A. Pross, M.P. McGrath, L. Radom, J. Chem. Phys. 103 (1995) 1878-1885.
28. V. Barone, M. Cossi, J. Phys. Chem. A 102 (1998) 1995-2001.
29. G. Brancato, N. Rega, V. Barone, J. Chem. Phys. 125 (2006) 164515-164525.
30. K. Wolinski, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112 (1990) 8251-8260.
31. P. Pulay, X. Zhou, F. Fogarasi, in: R. Fausto (Ed.), Recent Experimental and Computational Advances in Molecular Spectroscopy, Kluver, Academic, Netherlands, 1993, pp. 88-111.
32. A. Klam, COSMO-RS from Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design, Elsevier, Amsterdam, 2005.
33. P. Scott, L. Radom, J. Phys. Chem. 100 (1996) 16502-16513.
34. M. Alcolea Palafox, Int. J. Quant. Chem. 77 (2000) 661-684.
35. M. Alcolea Palafox, V.K. Rastogi, Spectrochim. Acta A 58 (2002) 411-440.
36. K. Szczepaniak, M.M. Szcześniak, W.B. Person, J. Phys. Chem. A 104 (2000) 3852-3863.
37. K. Szczepaniak, W.B. Person, D. Hadži, J. Phys. Chem. A 109 (2005) 6710-6724.
38. M. Alcolea Palafox, M. Gill, N.J. Nunez, V.K. Rastogi, L. Mittal, R. Sharma, Int. J. Quant. Chem. 103 (2005) 394-421.
39. Y.I. Binev, M.K. Georgieva, L.I. Daskalova, Spectrochim. Acta A 60 (2004) 2601-2610.
40. R. Dennington II, T. Keith, J. Millam, Gauss View, Version 4.1.2, Semichem. Inc., Shawnee Mission, KS, 2007.
41. J.H. Simpson, Organic Structure Determination Using 2-D NMR Spectroscopy, Academic Press, Elsevier, Amsterdam, 2008.
42. E. Pretsch, P. Bühlmann, C. Affolter, Structure Determination of Organic Compounds, Table of Spectral Data, Springer Verlag, Berlin, Heildelberg, 2000.
43. S.A. Richarsa, J.C. Hollerton, Essential Practical NMR for Organic Chemistry, John Wiley & Sons Ltd., 2011.
44. R. Dichfield, Mol. Phys. 27 (1974) 789-807.
45. B. OśmiaŁowski, E. Kolehmainen, R. Gawinecki, Magn. Res. Chem. 39 (2001) 334-340.
46. A. Katrusiak, J. Mol. Graph. Model 19 (2001) 363-367.