JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 68 No 1 (2023): Journal of the Chilean Chemical Society
Original Research Papers

8-(DI­METHYL­AMINO)-N,N-DI­METHYL­NAPHTHALEN-1-AMINIUM AND HYDROGENTEREPHTHALATE AS SYNTHONS FOR SUPRAMOLECULAR ARCHITECTURE

Andres Vega
Universidad Nacional Andres Bello
Bio
Duval Donoso
Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. Quillota 980, Viña del Mar, Chile
Carolina Muñoz
Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. Quillota 980, Viña del Mar, Chile
Nicolás Aravena
Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. Quillota 980, Viña del Mar, Chile
Published May 3, 2023
Keywords
  • hydrogenterephthalate,
  • Proton Sponge,
  • packing structure
How to Cite
Vega, A., Donoso, D., Muñoz, C., & Aravena, N. (2023). 8-(DI­METHYL­AMINO)-N,N-DI­METHYL­NAPHTHALEN-1-AMINIUM AND HYDROGENTEREPHTHALATE AS SYNTHONS FOR SUPRAMOLECULAR ARCHITECTURE . Journal of the Chilean Chemical Society, 68(1), 5745-5747. Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/2163

Abstract

8-(dimethylamino)-N,N-dimethyl­naphthalen-1-aminium hydrogenterephthalate (PSH+TPAH-) and 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium hydrogen-terephthalate hydrate (PSH+TPAH-·H2O) were prepared by the direct reaction of N1,N1,N8,N8-tetra­methyl­naphthalene-1,8-di­amine, Proton Sponge (PS) © and terephthalic acid (TPAH2) in a 1:1 stoichiometric relation. The structure of both salts is constructed on the base of 1D chains defined by hydrogen bonding of the anionic carboxylate end and the carboxylic acid of TPAH- anion. Additionally for the structure of PSH+TPAH-·H2O the water molecules connect this 1D chains through hydrogen bonds, then defining a 1D-belt. In both cases the PSH+ provides balance of charge among the chains.

2163.JPG

References

  1. Benoit, R.L., D. Lefebvre, and M. Fréchette, Basicity of 1,8-bis(dimethylamino)naphthalene and 1,4-diazabicyclo[2.2.2]octane in water and dimethylsulfoxide. Canadian Journal of Chemistry, 1987. 65(5): p. 996-1001.
  2. Cox, C., H. Wack, and T. Lectka, Strong Hydrogen Bonding to the Amide Nitrogen Atom in an “Amide Proton Sponge”: Consequences for Structure and Reactivity. Angewandte Chemie International Edition, 1999. 38(6): p. 798-800.
  3. CRC Handbook of Chemistry and Physics, ed. D.R. Lide. 2003, 2000 N. W. Corporate Blvd., Boca Raton, FL 33431: CRC Press.
  4. Cheng, Z., et al., Ultralong Phosphorescence from Organic Ionic Crystals under Ambient Conditions. Angewandte Chemie International Edition, 2018. 57(3): p. 678-682.
  5. Shi, C., et al., Geometric isotope effect of deuteration in a hydrogen-bonded host–guest crystal. Nature Communications, 2018. 9(1): p. 481.
  6. Mallinson, P.R., et al., From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene. Journal of the American Chemical Society, 2003. 125(14): p. 4259-4270.
  7. Sheldrick, G.M.S.N.V., Bruker AXS Inc., Madison, WI, USA, 2000.
  8. Sheldrick, G.M., A short history of SHELX. Acta Crystallogr A, 2008. 64(Pt 1): p. 112-22.
  9. Sheldrick, G.M., Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem, 2015. 71(Pt 1): p. 3-8.
  10. Parkin, A., K. Wozniak, and C.C. Wilson, From Proton Disorder to Proton Migration: A Continuum in the Hydrogen Bond of a Proton Sponge in the Solid State. Crystal Growth & Design, 2007. 7(8): p. 1393-1398.
  11. Fitzgerald, L.J. and R.E. Gerkin, Hydrogen bonding and C—H⋯O interactions in bis(8-dimethylamino-1-dimethylammonionaphthalene) [(DMANH+)2] 4,8-dicarboxynaphthalene-1,5-dicarboxylate dihydrate. Acta Crystallographica Section C, 1999. 55(9): p. 1556-1559.
  12. Fisher, M.G., et al., Hydrogen bonded networks in N–alkyl substituted thiourea platinum (II) oxocarbodianion and carboxylate salts. CrystEngComm, 2008. 10(9): p. 1180-1190.
  13. Cobbledick, R.E. and R.W.H. Small, The crystal structure of ammonium hydrogen terephthalate. Acta Crystallographica Section B, 1972. 28(10): p. 2924-2928.
  14. Kaduk, J., Terephthalate salts: salts of monopositive cations. Acta Crystallographica Section B, 2000. 56(3): p. 474-485.
  15. Jones, P.G., et al., Three Crystal Structures of Terephthalic Acid Salts of Simple Amines. Zeitschrift für Naturforschung B, 2009. 64(7): p. 865-870.
  16. Bellucci, L., et al., Luminescent sequence-dependent materials through a step by step assembly of RE1–1,4-benzendicarboxylate–RE2 (REx = Y3+, Eu3+ and Tb3+) architectures on a silica surface. Journal of Materials Chemistry C, 2019. 7(15): p. 4415-4423.

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP