Structure of 1-carboxymethylpyridinium-4-carboxylate inner salt studied by X-ray diffraction, DFT calculations, vibrational and NMR spectra

Journal of Molecular Structure

Volumn 933, Issue 1-3, 2009, Pages 20-29

  Barczynski P ^a   Katrusiak, A ^a   Koput, J ^a   Dega Szafran, Z ^a   Szafran, M ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

1 Carboxymethylpyridinium 4 carboxylate inner salt; DFT calculations; Electrostatic interactions; Hydrogen bonds; Spectroscopic methods; X ray diffraction

Indexed keywords

1-CARBOXYMETHYLPYRIDINIUM-4-CARBOXYLATE INNER SALT; B3LYP CALCULATIONS; CHARGED ATOMS; DFT CALCULATION; DFT CALCULATIONS; ELECTROSTATIC INTERACTIONS; ENERGY STABILIZATION; FT-IR SPECTRUM; FTIR; ISOTROPIC SHIELDING; LINEAR CORRELATION; NMR CHEMICAL SHIFTS; NMR SPECTRUM; RAMAN SPECTRUM; SPACE GROUPS; SPECTROSCOPIC METHODS; SPECTROSCOPIC TECHNIQUE; STABLE COMPLEXES; X RAY DATA;

ABSORPTION; ABSORPTION SPECTROSCOPY; BINDING SITES; CARBOXYLATION; COMPLEXATION; DIFFRACTION; ELECTROSTATICS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; RAMAN SPECTROSCOPY; SULFUR COMPOUNDS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS; X RAYS;

HYDROGEN BONDS;

EID: 67949098856     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.05.052     Document Type: Article

References (46)

1. Szafran M., Katrusiak A., Koput J., and Dega-Szafran Z. J. Mol. Struct. 846 (2007) 1
2. Cannon J.R., Edmonds J.S., Francesconi K.A., Raston C.L., Saunders J.B., Skelton B.W., and White A.H. Aust. J. Chem. 34 (1981) 787
3. Szafran M., Bartoszak-Adamska E., Koput J., and Dega-Szafran Z. J. Mol. Struct. 844-845 (2007) 140
4. Beilstein, 22(1) E III/IV, p. 330, 462.
5. In: Florkin M., and Stotz E.H. (Eds). Comprehensive Biochemistry (1965), Elsevier Publishing Company, Amsterdam 224
6. Szafran M., Katrusiak A., and Dega-Szafran Z. J. Mol. Struct. 827 (2007) 56
7. Szafran M., Dega-Szafran Z., Grundwald-Wyspiańska M., Barczyński P., and Pankowski M. Polish J. Chem. 76 (2002) 1191
8. Szafran M., Dega-Szafran Z., Katrusiak A., Stobiecka K., and Pankowski M. J. Mol. Struct. 649 (2003) 43
9. Szafran M., Koput J., Dega-Szafran Z., Katrusiak A., Pankowski M., and Stobiecka K. Chem. Phys. 289 (2003) 201
10. Szafran M., Koput J., Katrusiak A., and Dega-Szafran Z. J. Mol. Struct. 704 (2004) 45
11. Szafran M., Katrusiak A., Koput J., and Dega-Szafran Z. J. Mol. Struct. 784 (2006) 98
12. Szafran M., Koput J., Dega-Szafran Z., and Katrusiak A. J. Mol. Struct. 797 (2006) 66
13. Szafran M., Katrusiak A., and Dega-Szafran Z. J. Mol. Struct. 880 (2008) 77
14. Song L., Li H.-S., and Song B.-D. Acta Cryst. E62 (2006) o4656
15. Chen X.-M., and Mak T.C.W. J. Mol. Struct. 249 (1991) 135
16. Matsunaga S., Kamimura T., and Fusetani N. J. Nat. Prod. 61 (1998) 671
17. Wang X.-B., Dacres J.E., Yang X., Broadus K.M., Lis L., Wang L.-S., and Kass S.R. J. Am. Chem. Soc. 125 (2003) 296
18. KUMA KM4 CCD Software, version 161, Kuma Diffraction, Wrocław, Poland, 1999.
19. Sheldrick G.M. SHELXS-97, Program for Solution of Crystal Structures (1997), University of Göttingen, Germany
20. Sheldrick G.M. SHELXL-97, Program for Crystal Structure Refinement (1997), University of Göttingen, Germany
21. C.K. Johnson, ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976.
22. Stereochemical Workstation Operation Manual, Release 3.4, Siemens Analytical X-ray Instruments Inc. Madison, 1989.
23. 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..
24. Becke A.D. J. Chem. Phys. 98 (1993) 5648
25. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
26. Hehre W.J., Random L., Schleyer P.V.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1989), Wiley, New York
27. Speakman J.C. Struct. Bond. 12 (1972) 141
28. Chen X.-M., and Mak T.C.W. J. Mol. Struct. 221 (1990) 265
29. Szafran M., Katrusiak A., and Dega-Szafran Z. J. Mol. Struct. 794 (2006) 46
30. Morokuma K. J. Chem. Phys. 55 (1971) 1236
31. Kitaura K., and Morokuma K. Int. J. Quantum Chem. 10 (1976) 325
32. Umeyama H., and Morokuma K. J. Am. Chem. Soc. 99 (1977) 1316
33. Tomasi J. In: Ratajczak H., and Orville-Thomas W.J. (Eds). Molecular Interactions vol. 3 (1982), Wiley & Sons 119-181
34. Ramaeker R., Smith D.M.A., Smets J., and Adamowicz L. J. Mol. Struct. 513 (1999) 169
35. Novak A. Struct. Bond. 18 (1974) 177
36. Buder W.I., and Hopkins D.W. Photochem. Photobiol. 12 (1970) 439
37. Maddams W.F., and Southon M.J. Spectrochim. Acta 38A (1982) 459
38. Talsky G. Derivative Spectrophotometry (1994), VCR, Weinheim
39. Alcolea Palafox M., Gill M., Nunez N.J., Rastogi V.K., and Sharma L. Int. J. Quantum Chem. 103 (2005) 394 (and ref. cited therein)
40. Dichfield R. Mol. Phys. 27 (1974) 789
41. Forsyth D.A., and Sebag A.B. J. Am. Chem. Soc. 119 (1997) 9483
42. Ośmiałowski B., Kolehmainen E., and Gawinecki R. Magn. Res. Chem. 39 (2001) 334 (and ref. cited therein)
43. Dega-Szafran Z., Gdaniec M., Grundwald-Wyspiańska M., Kowalczyk I., and Szafran M. J. Mol. Struct. 322 (1994) 297
44. Szafran M., Katrusiak A., Kowalczyk I., Dega-Szafran Z., and Drozd M. J. Mol. Struct. 689 (2004) 213
45. Szafran M., Katrusiak A., and Dega-Szafran Z. J. Mol. Struct. 839 (2007) 99
46. Katrusiak A. J. Mol. Graph. Model. 19 (2001) 369