The structure of 4-(trimethylammonium)benzoic acid chloride studied by X-ray diffraction, DFT calculations, NMR and FTIR spectroscopy

Journal of Molecular Structure

Volumn 996, Issue 1-3, 2011, Pages 75-81

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

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

4 (trimethylammonium)benzoic acid chloride; DFT calculations; Electrostatic interactions; Hydrogen bonds; NMR and FTIR spectra; X ray diffraction

Indexed keywords

BENZOIC ACID; CARBOXY GROUPS; CHLORIDE IONS; DFT CALCULATION; FTIR; FTIR SPECTROSCOPY; ISOTROPIC SHIELDING; LINEAR CORRELATION; PROTONATED;

CARBOXYLIC ACIDS; CHEMICAL SHIFT; CHLORINE; CHLORINE COMPOUNDS; CRYSTAL STRUCTURE; DIFFRACTION; ELECTROSTATICS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN; IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

HYDROGEN BONDS;

EID: 79958027613     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2011.04.019     Document Type: Article

References (50)

1. X. Domingo, in: E.G. Lomax (Ed.), Amphoteric Surfactants Marcel Dekker, Inc. New York, Basel 1996, pp. 73-189.
2. R.G. Laughlin Langmuir 7 1991 842
3. E. Alcalde Adv. Heterocycl. Chem. 60 1994 197 259
4. A. Schmidt Adv. Heterocycl. Chem. 85 2003 67 171
5. Z. Dega-Szafran, E. Dulewicz, and M. Szafran Magn. Reson. Chem. 38 2000 43
6. R. Ruder, B. Schulz, G. Reck, D. Vollhardt, and J. Kriwanek Acta Cryst. B 56 2000 124
7. M. Szafran, I. Kowalczyk, A. Katrusiak, and Z. Dega-Szafran J. Mol. Struct. 651-653 2003 621
8. M. Szafran, A. Katrusiak, Z. Dega-Szafran, S. Dymarska, and M. Grundwald-Wyspiańska J. Mol. Struct. 609 2002 19
9. W.D. Ollis, S.P. Stanforth, and C.A. Ramsden Tetrahedron 41 1985 2239
10. G. Schaack Ferroelectrics 104 1990 147 (and references cited therein)
11. M. Szafran, J. Koput, Z. Dega-Szafran, and A. Katrusiak J. Mol. Struct. 700 2004 109
12. M. Szafran, A. Katrusiak, and Z. Dega-Szafran J. Mol. Struct. 827 2007 56
13. M. Szafran, A. Katrusiak, and Z. Dega-Szafran J. Mol. Struct. 839 2007 99
14. M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, M. Pankowski, and K. Stobiecki Chem. Phys. 289 2003 201
15. M. Szafran, A. Katrusiak, J. Koput, and Z. Dega-Szafran J. Mol. Struct. 704 2004 45
16. M. Szafran, J. Koput, Z. Dega-Szafran, and A. Katrusiak J. Mol. Struct. 797 2006 66
17. M. Szafran, A. Katrusiak, and Z. Dega-Szafran J. Mol. Struct. 794 2006 46
18. J. Picha, R. Cibulka, F. Liseka, P. Parik, and O. Pytela Collect. Czech. Chem. Commun. 69 2004 2239
19. J.T. Edsall, and J. Wyman Jr. J. Am. Chem. Soc. 57 1935 1964
20. M. Hojo, M. Utaka, and Z. Yoshida Tetrahedron 27 1971 4255
21. K.M. Broadus, and S.R. Kass J. Am. Chem. Soc. 122 2000 9014 (and references cited therein)
22. KUMA KM4 CCD Software, Version 161, Kuma Diffraction, Wroclaw, Poland 1999.
23. CrysAlis 162, Kuma Diffraction, Wroclaw, Poland, 1999.
24. G.M. Sheldrick Acta Crystallogr. A64 2008 112
25. C.K. Johnson ORTEPII. Report ORNL-5138 1976 Oak Ridge National Laboratory Tennessee, USA
26. Stereochemical Workstation Operation Manual, Release 3.4, Siemens Analytical X-ray Instruments Inc., Madison, 1989.
27. 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
28. A.D. Becke J. Chem. Phys. 98 1993 5648
29. A.D. Becke J. Chem. Phys. 107 1997 8554
30. C. Lee, W. Yang, and C.R. Parr Phys. Rev. B 37 1988 785
31. W.J. Hehre, L. Random, P.v.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1989 Wiley New York
32. V. Barone, and M. Cossi J. Phys. Chem. A 112 1998 1995
33. G. Brancato, N. Rega, and V. Barone J. Chem. Phys. 125 2006 164515
34. K. Wolinski, J.F. Hilton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 (and references cited therein)
35. A.P. Scott, and L. Radom J. Phys. Chem. 100 1996 16502
36. P. Pulay, X. Zhou, and G. Fogarasi R. Fausto, In Recent Experimental and Computational Advances in Molecular Spectroscopy 1993 Kluver Academic Netherlands 88 111
37. M. Alcolea Palafox Recent Res. Dev. Phys. Chem. 2 1998 213 (Transworld Research Network; Trivandrum, India)
38. M. Alcolea Palafox Int. J. Quantum. Chem. 77 2000 661
39. M. Alcolea Palafox, and V.K. Rastogi Spectrochim. Acta A 58 2002 411
40. K. Szczepaniak, M.M. Szczesniak, and W.B. Person J. Phys. Chem. A 104 2000 3852
41. K. Szczepaniak, W.B. Person, and D. Hadži J. Phys. Chem. A 109 2005 6710
42. M. Alcolea Palafox, M. Gill, N.J. Nunez, V.K. Rastogi, L. Mittal, and R. Sharma Int. J. Quantum Chem. 103 2005 394
43. Y.I. Binev, M.K. Georgieva, and L.I. Daskalova Spectrochim. Acta A 60 2004 2601
44. R. Dennington II, T. Keith, and J. Millan Gauss View, Version 4.1.2 2007 Semichem. Inc. Shawnee Mission, KS
45. J.H. Simpson Organic Structure Determination Using 2-D NMR Spectroscopy 2008 Academic Press, Elsevier, Amsterdam
46. R. Ditchfield Mol. Phys. 27 1974 789
47. A. Forsyth, and A.B. Sabag J. Am. Chem. Soc. 119 1997 9483
48. B. Ośmiałowski, E. Kolehmainen, and R. Gawinecki Magn. Res. Chem. 39 2001 334 (and references cited therein)
49. A.R. Katritzky, N.G. Akhmedov, A. Güven, E.F.V. Scriven, S. Majumder, R.G. Akhmedova, and C.D. Hall J. Mol. Struct. 783 2006 191
50. A. Katrusiak J. Mol. Graph. Model 19 2001 363