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Structural Systematics of the Anhydrous 1:1 Proton-Transfer Compounds of 3,5-Dinitrosalicylic Acid with Aniline and Monosubstituted Anilines

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Abstract

The crystal structures of the proton-transfer compounds of 3,5-dinitrosalicylic acid (DNSA) with a series of aniline-type Lewis bases (aniline, 2-hydroxyaniline, 2-methoxyaniline, 3-methoxyaniline, 4-fluoroaniline, 4-chloroaniline and 2-aminoaniline) have been determined and their hydrogen-bonding systems analysed. All are anhydrous 1:1 salts: [(C6H8N)+(C7H3N2O7)−] (1), [(C6H8NO)+(C7H3N2O7)−] (2), [(C7H10NO)+(C7H3N2O7)−] (3), [(C7H10NO)+(C7H3N2O7)−] (4), [(C6H7FN)+(C7H3N2O7)−] (5), [(C6H7ClN)+(C7H3N2O7)−] (6), and [(C6H9N2)+(C7H3N2O7)−] (7), respectively. Crystals of 1 and 6 are triclinic, space group P-1 while the remainder are monoclinic with space group either P21/n (2, 4, 5 and 7) or P21 (3). Unit cell dimensions and contents are: for 1, a = 7.2027(17), b = 7.5699(17), c = 12.9615(16) Å, α = 84.464(14), β = 86.387(15), γ = 75.580(14)°, Z = 2; for 2, a = 7.407(3), b = 6.987(3), c = 27.653(11) Å, β = 94.906(7)°, Z = 4; for 3, a = 8.2816(18), b = 23.151(6), c = 3.9338(10) Å, β = 95.255(19)°, Z = 2; for 4, a = 11.209(2), b = 8.7858(19), c = 15.171(3) Å, β = 93.717(4)°, Z = 4; for 5, a = 26.377(3), b = 10.1602(12), c = 5.1384(10) Å, β = 91.996(13)°, Z = 4; for 6, a = 11.217(3), b = 14.156(5), c = 4.860(3) Å, α = 99.10(4), β = 96.99(4), γ = 76.35(2)°, Z = 2; for 7, a = 12.830(4), b = 8.145(3), c = 14.302(4) Å, β = 102.631(6)°, Z = 4. In all compounds at least one primary linear intermolecular N+–H⋯O(carboxyl) hydrogen-bonding interaction is present which, together with secondary hydrogen bonding results in the formation of mostly two-dimensional network structures, exceptions being with compounds 4 and 5 (one-dimensional) and compound 6 (three-dimensional). In only two cases (compounds 1 and 4), are weak cation–anion or cation–cation π–π interactions found while weak aromatic C–H⋯O interactions are insignificant. The study shows that all compounds fit the previously formulated classification scheme for primary and secondary interactive modes for proton-transfer compounds of 3,5-dinitrosalicylic acid but there are some unusual variants.

Graphical Abstract

The crystal structure determinations of the anhydrous 1:1 proton-transfer compounds of 3,5-dinitrosalicylic acid with aniline and a set of six monosubstituted anilines (2-hydroxy-, 2-methoxy-, 3-methoxy-, 4-fluoro-, 4-chloro- and 2-aminoaniline) have allowed the hydrogen-bonding systematics to be examined.

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Acknowledgments

The authors acknowledge financial support from the Faculty of Science and Technology, Queensland University of Technology, the School of Biomolecular and Physical Sciences, Griffith University and the School of Chemistry, University of Melbourne.

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Authors and Affiliations

  1. Faculty of Science and Technology, Queensland University of Technology, G.P.O. Box 2434, Brisbane, QLD, 4001, Australia

    Graham Smith

  2. School of Biomolecular and Physical Sciences, Griffith University, Nathan, QLD, 4111, Australia

    Urs D. Wermuth & Peter C. Healy

  3. BIO-21, Molecular Science and Biotechnology, University of Melbourne, Parkville, VIC, 3010, Australia

    Jonathan M. White

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  1. Graham Smith
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Correspondence to Graham Smith.

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Smith, G., Wermuth, U.D., Healy, P.C. et al. Structural Systematics of the Anhydrous 1:1 Proton-Transfer Compounds of 3,5-Dinitrosalicylic Acid with Aniline and Monosubstituted Anilines. J Chem Crystallogr 41, 1649–1662 (2011). https://doi.org/10.1007/s10870-011-0153-0

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