Skip to main content
SpringerLink
Log in

Synthesis, Crystal Structure Analysis, Small Cluster Geometries and Energy Study of (E)-Ethyl-4-(2-(thiofen-2-ylmethylene)hydrazinyl)benzoate

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Derivatives hydrazone are attributed interesting pharmacological properties. The compound under study (E)-ethyl 4-(2-(thiofen-2-ylmethylene) hydrazinyl)benzoate (1), crystallized from ethanol as translucent light yellow thin plates. They are monoclinic, space group P21/c, with unit cell parameters a = 8.846(6), b = 20.734(14), c = 7.583(5) Å, β = 95.743(13)°, V = 1383.8(16) Å3. Three hydrogen bonds and two intermolecular π-interaction perpendiculars to the hydrogen bonds patterns are observed in the crystal structure. A detailed description of these interactions will be presented. Also, semiempirical calculations (PM6) show the formation in the gas phase of a supramolecular chain, emulating the C(8) graph set seen in the crystal structure of the compound.

Graphical Abstract

The synthesis and crystal structure of the title compound, C14H14N2O2S, is reported.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Rollas S, Küçükgüzel G (2007) Biological activities of hydrazone derivatives. Molecules 12:1910–1939

    Article  CAS  Google Scholar 

  2. Abdel-Zaher E, Dib H, Al-Awadi N, Elnagdi M (2007) Chemistry of carbofunctionally substituted hydrazones. Arkivoc II:272–315

    Google Scholar 

  3. Belskaya N, Dehaen W, Bakulev V (2010) Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions. Arkivoc I:275–332

    Article  Google Scholar 

  4. Alvarado Y, Álvarez-Mon M, Baricelli J, Caldera-Luzardo J, Cubillán N, Ferrer-Amado G, Hassanhi M, Marrero-Ponce Y, Mancilla V, Rocafull M, San Antonio-Sánchez M, Ojeda-Andara J, Thomas L (2010) Solubility of thiophene-, furan- and pyrrole-2-carboxaldehyde phenylhydrazone derivatives in 2.82 mol L–1 aqueous DMSO at 298.15 K, inhibition of lymphoproliferation and tubulin polymerization: a study based on the scaled particle theory. J Sol Chem 39:1099–1112

    Article  CAS  Google Scholar 

  5. Alvarado Y, Baricelli J, Caldera-Luzardo J, Cubillán N, Ferrer-Amado G, Marrero-Ponce Y, Mancilla V, Rocafull M, Ojeda-Andara J, Thomas L, Vera-Villalobos J, Morales-Toyo M (2011) Thermodynamics of solution, interaction with calf thymus DNA and anticancer activity of phenylhydrazone derivatives. J Sol Chem. 40(5):26–39

    Article  CAS  Google Scholar 

  6. Alvarado Y, Caldera-Luzardo J, Ferrer-Amado G, Mancilla-Labarca V, Michelena E (2007) Determination of the apparent molar refraction and partial molar volume at infinite dilution of thiophene-, pyrrole- and furan-2-carboxaldehyde phenylhydrazone derivatives in acetonitrile at 293.15 K. J Sol Chem 36(6):1–11

    Article  CAS  Google Scholar 

  7. Alvarado Y, Ballestas-Barrientos A, Cubillán N, Morales-Toyo M, Restrepo J, Ferrer-Amado G (2012) Peferential solvation of thiophene and furan-2-carboxaldehyde phenylhydrazone derivatives in DMSO-Water and DMSO-n-Octanol mixtures. Spectrochim Acta Part A 103:361–367

    Google Scholar 

  8. Bruker (1998b) SAINT: SAX Area-detector Integration, Version 5.01, Bruker AXS, Inc., Madison, Wisconsin, USA

  9. Sheldrick G (2008) A short history of SHELX. Acta Cryst A 64:112–122

    Article  CAS  Google Scholar 

  10. Hobza P (2011) The calculation of intermolecular interaction energies. Annu Rep Prog Chem Sect C 107:148–168

    Article  CAS  Google Scholar 

  11. Stewart J (2007) Optimization of Parameters for Semiempirical Methods V: modification of NDDO Approximations and Application to 70 Elements. J Mol Modeling 13:1173–1213

    Article  CAS  Google Scholar 

  12. Korth M, Pitoňák M, Rězácˇ J, Hobza P (2010) A transferable H-bonding correction for semiempirical quantum-chemical methods. J Chem Theory Comput 6:344–352

    Article  CAS  Google Scholar 

  13. Karpfen A (2002) Cooperative effects in hydrogen bonding. Adv Chem Phys 123:469–510

    Article  CAS  Google Scholar 

  14. Jurečka P, Černy J, Hobza P, Salahub D (2007) Density functional theory augmented with an empirical dispersion term. Interaction energies and geometries of 80 noncovalent complexes compared with ab initio quantum mechanics calculations. J Comput Chem 28(2):555–569

    Article  Google Scholar 

  15. Karpfen A (1997) In: Scheiner S (ed) Molecular interacctions from.van der Waals to strongly bond molecular complexes. Wiley, Chichester, p 265

    Google Scholar 

  16. Allen F (2002) The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Cryst B 58:380–388

    Article  Google Scholar 

  17. Kitamura T, Sato T, Mori M (2001) Unexpected results of enyne metathesis using a ruthenium complex containing an N-heterocyclic carbene ligand. Chem Commun 14:1258–1259

    Article  Google Scholar 

  18. O’Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA (2005) Total synthesis of (+)-Lithospermic acid by asymmetric intramolecular alkylation via catalytic C−H bond activation. J Am Chem Soc 127:13496–13497

    Article  Google Scholar 

  19. Williams DE, Craycroft DJ (1987) Nonbonded hydrogen···hydrogen repulsion energy from ab initio SCF calculations of methane, ammonia, water, and methanol dimmers. J Phys Chem 91:6365–6373

    Article  CAS  Google Scholar 

  20. Rincón L, Almeida R, García-Aldea D, Diez y Riega H (2001) Hydrogen bond cooperativity and electron delocalization in hydrogen fluoride clusters. J Chem Phys 114:5552–5562

    Article  Google Scholar 

  21. Brandenburg K, Putz H (2005) DIAMOND. Crystal Impact GbR, Bonn

    Google Scholar 

  22. ACD/ChemSketch Freeware (2006) version 10.00, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com

Download references

Acknowledgments

The authors thank Fondo Nacional de Ciencia, Tecnología e Innovación (FONACIT Proyecto de apoyo a Grupos No. G-2005000403) and grant LOCTI-2007-0003, Instituto Zuliano de Investigaciones Tecnológicas (INZIT), CONDES-LUZ, and Petroregional del Lago S. A. (PERLA) for partial financial support of this work, and to Prof. Graciela Diaz de Delgado for helpful discussions.

Author information

Authors and Affiliations

  1. Laboratorio de Caracterización Molecular y Biomolecular (LCMB), Departamento de Investigación en Tecnología de los Materiales y del Ambiente (DITeMA), Instituto Venezolano de Investigaciones Científicas (IVIC), 4001, Maracaibo, Venezuela

    Miguel Morales-Toyo, Ysaías J. Alvarado & Jelen Restrepo

  2. Laboratorio de Procesos Dinámicos en Química, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, 5101, Mérida, Venezuela

    Luis Seijas

  3. Unidad de Caracterización y Estructura de Materiales, Instituto Zuliano de Investigaciones Tecnológicas, 4001, La Cañada de Urdaneta, Venezuela

    Julia Bruno-Colmenarez

  4. Laboratorio de materiales para tecnologías emergentes (LaMTE), Departamento de Investigación en Tecnología de los Materiales y del Ambiente (DITeMA), Instituto Venezolano de Investigaciones Científicas (IVIC), 4001, La Cañada de Urdaneta, Venezuela

    Reinaldo Atencio

Authors
  1. Miguel Morales-Toyo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ysaías J. Alvarado
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jelen Restrepo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Luis Seijas
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Reinaldo Atencio
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Julia Bruno-Colmenarez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Julia Bruno-Colmenarez.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Morales-Toyo, M., Alvarado, Y.J., Restrepo, J. et al. Synthesis, Crystal Structure Analysis, Small Cluster Geometries and Energy Study of (E)-Ethyl-4-(2-(thiofen-2-ylmethylene)hydrazinyl)benzoate. J Chem Crystallogr 43, 544–549 (2013). https://doi.org/10.1007/s10870-013-0455-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-013-0455-5

Keywords

Search

Navigation