Structure and properties of the 1:2 complex of 1,4-dicarboxymethyl-1,4-dimethylpiperazinium inner salt (di-betaine) with p-hydroxybenzoic acid studied by X-ray, DFT, FTIR and NMR methods

Journal of Molecular Structure

Volumn 797, Issue 1-3, 2006, Pages 82-91

  Dega Szafran, Z ^a   Katrusiak, A ^a   Szafran, M ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

1,4 Dicarboxymethyl 1,4 dimethylpiperazinium inner salt; DFT calculations; FTIR; Hydrogen bonds; NMR spectra; p Hydroxybenzoic acid; X ray diffraction

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; X RAY DIFFRACTION ANALYSIS;

1,4-DICARBOXYMETHYL-1,4-DIMETHYLPIPERAZINIUM INNER SALT; CENTROSYMMETRIC TRIMOLECULAR COMPLEX; DFT CALCULATIONS; P-HYDROXYBENZOIC ACID;

ORGANIC COMPOUNDS;

EID: 33748710688     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2006.02.060     Document Type: Article

References (36)

1. In: Jauristi E. (Ed). Conformational Behavior of Six-Membered Rings Analysis Dynamic and SteVCH Publishers (1995), VCH Publishers, New York
2. Eliel E.L., Wilen S.H., and Mander L.N. Stereochemistry of Organic Compounds (1994), Wiley, New York
3. Freeman F., Tsegai Z.M., Kasner M.L., and Hehre W.J. J. Chem. Educ. 77 (2000) 661 and references cited therein
4. Lambert J.B., and Featherman S.I. Chem. Rev. 75 (1975) 611
5. Topsom R.D. Prog. Phys. Org. Chem. 12 (1976) 1
6. Kaloustian M.K., Denis N., Mager S., Evans S.A., Alcudia F., and Eliel E.L. J. Am. Chem. Soc. 98 (1976) 956
7. Szafran M., Dega-Szafran Z., Taimattam R., and Jaskólski M. J. Mol. Struct. 706 (2004) 49
8. Dega-Szafran Z., Tykarska E., Dulewicz E., and Szafran M. J. Mol. Struct. 605 (2002) 319
9. Dega-Szafran Z., Szafran M., Dulewicz E., Addlagatta A., and Jaskólski M. J. Mol. Struct. 654 (2003) 71
10. Belostotskii A.M., Gottlieb H.E., Aped P., and Hassner A. Chem. Eur. J. 5 (1999) 449 and references cited therein
11. Smith D.R., Curry J.W., and Eifert R.L. J. Am. Chem. Soc. 72 (1950) 2969
12. Baltzly R. J. Am. Chem. Soc. 76 (1954) 1164
13. Baltzly R., Ide W.S., and Lorz E. J. Am. Chem. Soc. 77 (1955) 4809
14. Harfenist M. J. Am. Chem. Soc. 79 (1957) 2211
15. Devinsky F., Lacko I., and Mlynarčik D. Coll. Czech. Chem. Commun. 47 (1982) 1130
16. Ziegler E., and Wittmann H. Monatsh. Chem. 116 (1985) 821
17. Dega-Szafran Z., Jaskólski M., Kurzyca I., Barczyński P., and Szafran M. J. Mol. Struct. 614 (2002) 23
18. Parkin A., Oswald I.D.H., and Parsons S. Acta Crystallogr. B 60 (2004) 219
19. Dega-Szafran Z., Katrusiak A., and Szafran M. J. Mol. Struct. 785 (2006) 160
20. Hermans J., Leach S.L., and Scheraga H.A. J. Am. Chem. Soc. 85 (1963) 1390
21. Sheldrick M.G. SHELXS-97. Program for the Solution of Crystal Structures (1997), University of Göttingen, Germany
22. Sheldrick M.G. SHELXL-97. Program for Crystal Structure Refinement (1997), University of Göttingen, Germany
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 C.01, Wallingford, CT, 2004.
24. Becke A.D. Phys. Rev. A 38 (1988) 3098
25. Becke A.D. J. Chem. Phys. 98 (1993) 5648
26. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
27. Hehre W.J., Radom L., Schleyer P.v.R., and Pople A.J. Ab Initio Molecular Orbital Theory (1989), Wiley, New York
28. Nelson J.H. Nuclear Magnetic Resonance Spectroscopy (2003), Pearson Educations, Inc, Upper Saddle River, NJ
29. Martin G.E., and Zektzer A.S. Two-Dimensional NMR Methods for Establishing Molecular Connectivity (1988), VCH, Weinheim
30. Williams D.H., and Fleming I. Spectroscopic Methods in Organic Chemistry. fifth ed. (1996), The McGraw-Hill Companies, London
31. Coddington J.M., and Taylor M.J. Spectrochim. Acta 46A (1990) 1487
32. Dega-Szafran Z., Szafran M., Szymusiak H., Zieliński R., and Przedwojska M. J. Mol. Struct. 744-747 (2005) 457
33. Dega-Szafran Z., Dutkiewicz D., Kosturkiewicz Z., Przedwojska M., and Szafran M. J. Mol. Struct. 649 (2003) 257
34. Forsyth D.A., and Sebag A.B. J. Am. Chem. Soc. 119 (1997) 9483
35. Sebag A.B., Forsyth D.A., and Plante M.A. J. Org. Chem. 66 (2001) 7967
36. Ośmiałowski B., Kolehmainen E., and Gawinecki R. Magn. Reson. Chem. 39 (2001) 334