Hydrogen-bonding network in the organic salts of 4-nitrobenzoic acid

• Authors: Yurii Chumakov , Yurii Simonov , Mata Grozav , Manuela Crisan , Gabriele Bocelli , Andrey Yakovenko , Dmitry Lyubetsky
• Languages of publication: EN

Abstracts

EN

The crystal structures of six novel salts of 4-nitrobenzoic acid - namely, 2-hydroxyethylammonium 4-nitrobenzoate (I), 2-hydroxypropylammonium 4-nitrobenzoate (II), 1-(hydroxymethyl)propylammonium 4-nitrobenzoate (III), 3-hydroxypropylammonium 4-nitrobenzoate (IV), bis-(2-hydroxyethylammonium) 4-nitrobenzoate (V), morpholinium 4-nitrobenzoate (VI) - containing the same anion but different cations have been studied. The ionic forms of I-VI serve as building blocks of the supramolecular architecture, and in crystals they are held together via ionic N-H···O and O-H···O hydrogen bonds. In the crystal packing the building blocks of I-III are self-assembled via N-H...O, O-H···O and C-H...O hydrogen bonds to form the chains which are further consolidated into two-dimensional layers by the same type of interactions. In IV-VI the chain-like structures have been generated by building blocks.

Keywords

EN

Hydrogen bonding; salts of 4-nitrobenzoic acid; molecular building blocks

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2006
• Volume: 4
• Issue: 3
• Pages: 458-475

Dates

published

1 - 9 - 2006

online

1 - 9 - 2006

Contributors

author

Yurii Chumakov

• Institute of Applied Physics, Academy of Sciences of Moldova, MD-2028, Kishinev, Moldova

author

Yurii Simonov

• Institute of Applied Physics, Academy of Sciences of Moldova, MD-2028, Kishinev, Moldova

author

Mata Grozav

• Institute of Chemistry Timisoara, Romanian Academy, RO-300223, Timisoara, Romania

author

Manuela Crisan

• Institute of Chemistry Timisoara, Romanian Academy, RO-300223, Timisoara, Romania

author

Gabriele Bocelli

• IMEM-CNR, Parco Area dele Scienze, I-43010, Fontanini-Parma, Italy

author

Andrey Yakovenko

• Institute of Organoelement Compounds, Russian Academy of Sciences, R-117 813, Moscow, Russia

author

Dmitry Lyubetsky

• Institute of Organoelement Compounds, Russian Academy of Sciences, R-117 813, Moscow, Russia

References

• [1] J.C. McDonald, P.C. Dorrestein and M.M. Pilley: “Design of Supramolecular Layers via Self-Assembly of Imidazole and Carboxylic Acids”, Crys. Growth Des., Vol. 1, (2001), pp. 29–38. http://dx.doi.org/10.1021/cg000008k[Crossref]
• [2] K.M. O’Connor and O.I. Corrigan: “Preparation and Charactersation of a Range of Diclofenac salts”, Int. J. Pharm., Vol. 226, (2001), pp. 163–179. http://dx.doi.org/10.1016/S0378-5173(01)00800-6[Crossref]
• [3] M. Laichici and M. Goian: “The Auxin Activity of some Benzoic Acid Salts with Ethanolamines on Plants”, Proc. Rom. Acad. B, Vol. 5, (2003), pp. 162–164.
• [4] M. Laichici, M. Mercea, M. Grozav, Gh. Ilia: “The Study of the Growth Regulating Effect of 2-Hydroxyethyldimethyl-ammonium-3,5-Diaminobenzoate (XIIa) on the Monocotyledonous and Dicotyledonous Plants”, In: 4 th International Conference of the Chemical Societies of the South-East European Countries, Belgrade, July 18–21, 2004, B-P 26, Vol. II, Serbian Chemical Society, 2004, p. 186.
• [5] K. Jayaraman, A. Chounhury and C.N.R. Rao: “Sulfates of Organic Diamines: Hydrogen-Bonded Structures and Properties”, Sol. State Sci., Vol. 4, (2002), pp. 413–422. http://dx.doi.org/10.1016/S1293-2558(02)01269-4[Crossref]
• [6] A. Ballabh, D.R. Trivedi and P. Dastidar: “Ascertaining the 1D Hydrogen-Bonded Network in Organic Ionic Solids”, Cryst. Growth Des., Vol. 5, (2005), pp. 1545–1553. http://dx.doi.org/10.1021/cg050020i[Crossref]
• [7] J.-M. Lehn: “Perspectives in Supramolecular Chemistry-From Molecular Recognition towards Molecular Information Processing and Self-Organization”, Angew. Chem. Int. Ed. Engl., Vol. 29, (1990), pp. 1304–1319. http://dx.doi.org/10.1002/anie.199013041[Crossref]
• [8] M. Grozav and M. Crisan: “Ammonium Salts of Halogeno-Substituted Benzoic Acids with Ethanolamine, Potential Bioregulators”, e-J. Environ. Agr. Food Chem., Vol. 3, (2004), http://ejeafche.uvigo.es.
• [9] M. Grozav, I. Neamtiu, M. Dorosencu, M. Mercea and M. Laichici: “New Quinoline Salts of the Carboxylic Acids with Potential Biological Activity. 2. Salts of Acetic, Chloroacetic Acids and Oxalic Acid”, Rev. Chim. (Bucharest), Vol. 55, (2004), pp. 36–38.
• [10] M. Dorosencu, R. Rad, M. Grozav and I. Neamtiu: “The Quantitative Determination of some Quaternary Ammonium Salts of Benzoic Acids” Ann. West Univ. Timisoara, Vol. 10, (2001), pp. 337–341.
• [11] SHELXTL-NT 5.1, Bruker Axs Inc., 6300 Enterprise Lane, Madison, Wi 53719-1173, USA.
• [12] G.M. Sheldrick: SHELXL-97 Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997.
• [13] J. Grell, J. Bernstein and G. Tinhofer: “Graph-set analysis of hydrogen-bond patterns: some mathematical concepts”, Acta Crystallogr., Vol. B56, (2000), pp. 166–180. [Crossref]
• [14] A.L. Spek: “Single-Crystal Structure Validation with the Program PLATON”, J. Appl. Cryst., Vol. 36, (2003), pp. 7–13. http://dx.doi.org/10.1107/S0021889802022112[Crossref]
• [15] C.A. Hunter, K.R. Lawson, J. Perkins and J. Urch: “Aromatic Interactions”, J. Chem. Soc., Perkin Trans. 2, (2001), pp. 651–669.
• [16] D.E. Lynch and I. McClenaghan: “Three 2-aminopurine derivatives”, Acta Crystallogr., Vol. C59, (2003), pp. 53–56.

Identifiers

DOI

10.2478/s11532-006-0023-3