Synthesis, characterization and crystal structure of a new azo-Schiff base "ethyl 2-((E)-(4-((E)-(4-ethylphenyl)diazenyl)-2-hydroxybenzylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate"

Document Type : Original Article

Authors

Abstract

A new azo-Schiff base"Ethyl 2-((E)-(4-((E)-(4-ethylphenyl)diazenyl)-2-hydroxybenzylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate" was prepared by the reaction of "Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate" and "(E)-5-((4-ethylphenyl)diazenyl)-2-hydroxybenz aldehyde" (1:1 molar ratio) in MeOH under reflux condition. The structure of compound was studied by elemental analysis, including IR and 1HNMR spectroscopy and single crystal X-ray diffraction method. The synthesized compound has been crystallized in triclinic system with P < /em>ī space group and a = 9.752 (2)Å, b = 10.349(2)Å, c = 13.263(3)Å, α = 87.72(3)˚, β = 75.80(3)˚, γ = 62.21(3)˚ cell parameters. The final R value is 0.098 for 4038 independent reflections. X-ray diffraction results confirm the planar geometric structure with a slight deviation and intermolecular hydrogen bond for the compound.

Keywords

References

  1. [1] Gladgych J. Mz., Hartley D., "Comprehensive Organic Chemistry",Pergamon. Oxford 2 (1979) 61-130.
  2. [1] Gladgych J. Mz., Hartley D., "Comprehensive Organic Chemistry",Pergamon. Oxford 2 (1979) 61-130.
  3. [2] Ginsburg D., "Concerning Amines: Their Properties, Preparation and Reactions", PergamonOxford (1967) 62-69. [DOI:10.1016/B978-0-08-011913-7.50014-8]
  4. [2] Ginsburg D., "Concerning Amines: Their Properties, Preparation and Reactions", PergamonOxford (1967) 62-69. [DOI:10.1016/B978-0-08-011913-7.50014-8]
  5. [3] Spitz R.d., "In Kirk-Othmerncyclopedia of Chemical Technology", Wiley New York7 (1979) 580.
  6. [3] Spitz R.d., "In Kirk-Othmerncyclopedia of Chemical Technology", Wiley New York7 (1979) 580.
  7. [4] Tassoni A., Germana A.M., Bagni N., "Free and conjugated polyamine content in Citrus sinensisOsbeck, cultivar Brasiliano N.L. 92, a Navel orange, at different maturation stages",Food Chem 87 (2004) 537-541. [DOI:10.1016/j.foodchem.2004.01.001]
  8. [4] Tassoni A., Germana A.M., Bagni N., "Free and conjugated polyamine content in Citrus sinensisOsbeck, cultivar Brasiliano N.L. 92, a Navel orange, at different maturation stages",Food Chem 87 (2004) 537-541. [DOI:10.1016/j.foodchem.2004.01.001]
  9. [5] Hartman H., Schulze M., Guenther R., "Nucleophilic substitution in arylazo phenols-a simple route for preparing chlorosubstitutedazobenzenes",Dyes and Pigments 15 (1991) 255-262. [DOI:10.1016/0143-7208(91)80010-7]
  10. [5] Hartman H., Schulze M., Guenther R., "Nucleophilic substitution in arylazo phenols-a simple route for preparing chlorosubstitutedazobenzenes",Dyes and Pigments 15 (1991) 255-262. [DOI:10.1016/0143-7208(91)80010-7]
  11. [6] Peters A.T., Chisowa E.,"Colour-constitution relationships in 2-acylamino-4-N,N-diethylaminoazobenzene disperse dyes", Dyes and Pigments 22 (1993) 223-238. [DOI:10.1016/0143-7208(93)80015-S]
  12. [6] Peters A.T., Chisowa E.,"Colour-constitution relationships in 2-acylamino-4-N,N-diethylaminoazobenzene disperse dyes", Dyes and Pigments 22 (1993) 223-238. [DOI:10.1016/0143-7208(93)80015-S]
  13. [7] Ho M.S., Natansohn A.,Rochon P., "Azo Polymers for Reversible Optical Storage. 7. The Effect of the Size of the Photochromic Groups",Macromolecules 28 (1995) 6124-6127. [DOI:10.1021/ma00122a020]
  14. [7] Ho M.S., Natansohn A.,Rochon P., "Azo Polymers for Reversible Optical Storage. 7. The Effect of the Size of the Photochromic Groups",Macromolecules 28 (1995) 6124-6127. [DOI:10.1021/ma00122a020]
  15. [8] Patel A.A.,Mehta G.A.,"Synthesis of novel heterocyclic compounds and their biological evalution", Der Pharma Chemical 2 (2010) 215-223.
  16. [8] Patel A.A.,Mehta G.A.,"Synthesis of novel heterocyclic compounds and their biological evalution", Der Pharma Chemical 2 (2010) 215-223.
  17. [9] Dalbir S.S., Mohan P., Sharma J., "synthesis and evaluation of some novel piperidinothiophenes as potential antioxidant and anti-inflammatory agents", Acta. Pharm. Sci49 (2007) 29-38.
  18. [9] Dalbir S.S., Mohan P., Sharma J., "synthesis and evaluation of some novel piperidinothiophenes as potential antioxidant and anti-inflammatory agents", Acta. Pharm. Sci49 (2007) 29-38.
  19. [10] Gadad A.K.,Kumar H.,Shishoo C.J.,Mkhazi I.,Mahajanshetti K.S., "Synthesis of some 2-Aminoacetylamino-3-carboethoxy/anilido-4,5,6,7-tetrahydrobenzo [b] Thiophenes for Local Anesthetic Activity", Indian J. Chem.Soc33 (1994) 298-301.
  20. [10] Gadad A.K.,Kumar H.,Shishoo C.J.,Mkhazi I.,Mahajanshetti K.S., "Synthesis of some 2-Aminoacetylamino-3-carboethoxy/anilido-4,5,6,7-tetrahydrobenzo [b] Thiophenes for Local Anesthetic Activity", Indian J. Chem.Soc33 (1994) 298-301.
  21. [11] Gillespie E., Dungan K.M., Gomol A.W., Seidehamel R.J.,"Selected immunologic properties oftiprinast, a non-steroidal antiallergy agent",Int.Immuno 5 (1985) 655-660. [DOI:10.1016/0192-0561(85)90149-3]
  22. [11] Gillespie E., Dungan K.M., Gomol A.W., Seidehamel R.J.,"Selected immunologic properties oftiprinast, a non-steroidal antiallergy agent",Int.Immuno 5 (1985) 655-660. [DOI:10.1016/0192-0561(85)90149-3]
  23. [12] Mishra R.,Tomar I.,Singhal S.,JhaK.K.,"Facile synthesis of thioazolidinones bearing thiophene nucles as antimicrobial agents",Scholars Libraray Der Pharma Chemical (2012) 489-496.
  24. [12] Mishra R.,Tomar I.,Singhal S.,JhaK.K.,"Facile synthesis of thioazolidinones bearing thiophene nucles as antimicrobial agents",Scholars Libraray Der Pharma Chemical (2012) 489-496.
  25. [13] Chambhare R.V., Khadse B.G.,Bonde A.S., Bahekar R.H.,"Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents", Eur J, Med Chem38 (2003) 89-100. [DOI:10.1016/S0223-5234(02)01442-3]
  26. [13] Chambhare R.V., Khadse B.G.,Bonde A.S., Bahekar R.H.,"Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents", Eur J, Med Chem38 (2003) 89-100. [DOI:10.1016/S0223-5234(02)01442-3]
  27. [14] Shlpa C.,Dipak S.,Vimukta S.,"Comparative study of microwave and conventional synthesis and pharmacological activity of pyrimidines: a review", J.Pharma Biomedical Sci1(2012) 15-22.
  28. [14] Shlpa C.,Dipak S.,Vimukta S.,"Comparative study of microwave and conventional synthesis and pharmacological activity of pyrimidines: a review", J.Pharma Biomedical Sci1(2012) 15-22.
  29. [15] Botros, "Azomethine dyes derived from an o-hydoxy aromatic aldehyde and a 2-aminopyridine", US Patent 405 (1977) 1119-1128.
  30. [15] Botros, "Azomethine dyes derived from an o-hydoxy aromatic aldehyde and a 2-aminopyridine", US Patent 405 (1977) 1119-1128.
  31. [16] Ispir E., "The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes",Dyes and Pigments 82 (2009) 13-19. [DOI:10.1016/j.dyepig.2008.09.019]
  32. [16] Ispir E., "The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes",Dyes and Pigments 82 (2009) 13-19. [DOI:10.1016/j.dyepig.2008.09.019]
  33. [17] Dincapl H., Toker F., Durucasu, Avcibasi N., Icli S., "New thiophene-based azo ligands containing azo methane group in the main chain for the determination of copper(II) ions", Dyes and Pigment 75 (2007) 11-24. [DOI:10.1016/j.dyepig.2006.05.015]
  34. [17] Dincapl H., Toker F., Durucasu, Avcibasi N., Icli S., "New thiophene-based azo ligands containing azo methane group in the main chain for the determination of copper(II) ions", Dyes and Pigment 75 (2007) 11-24. [DOI:10.1016/j.dyepig.2006.05.015]
  35. [18] Menati S., Azadbakht A., Azadbakht R., Taeb A., Kakanejadifard A.,"Synthesis, characterization, and electrochemical study of some novel azo-containing Schiff bases and their Ni(II) complexes", Dyes and Pigments 98 (2013) 499-506. [DOI:10.1016/j.dyepig.2013.04.009]
  36. [18] Menati S., Azadbakht A., Azadbakht R., Taeb A., Kakanejadifard A.,"Synthesis, characterization, and electrochemical study of some novel azo-containing Schiff bases and their Ni(II) complexes", Dyes and Pigments 98 (2013) 499-506. [DOI:10.1016/j.dyepig.2013.04.009]
  37. [19] Kurmar S.B., Bhattacharyya S., Outta S.K., Tiekink E.R.T., Chaudhury M., "Mononuclear manganese(III) complexes of a heterodonor (N2OS) ligand containing thiolate-type sulfur: synthesis, structure, redox and spectroscopic properties",J. Chem.SOC.Dalton.Trns (1995) 2619-2627. [DOI:10.1039/dt9950002619]
  38. [19] Kurmar S.B., Bhattacharyya S., Outta S.K., Tiekink E.R.T., Chaudhury M., "Mononuclear manganese(III) complexes of a heterodonor (N2OS) ligand containing thiolate-type sulfur: synthesis, structure, redox and spectroscopic properties",J. Chem.SOC.Dalton.Trns (1995) 2619-2627. [DOI:10.1039/dt9950002619]
  39. [20] Tahriri M., Yousefi M.,Tabatabaee M., Mehrani K.,Dehghani A., shkezari M., Dusek M.,"Crystal Structure of N'-(2-hydroxy-3-methoxy benzylidene)-4-nitro benzenesulfonylhydrazide and 1,2-bis(2-hydroxy-3-methoxy-benzylidenehydrazine) as a co-crystalline compound",Iran J. Cryst. Miner26 (2018) 245-250. [DOI:10.29252/ijcm.26.1.245]
  40. [20] Tahriri M., Yousefi M.,Tabatabaee M., Mehrani K.,Dehghani A., shkezari M., Dusek M.,"Crystal Structure of N'-(2-hydroxy-3-methoxy benzylidene)-4-nitro benzenesulfonylhydrazide and 1,2-bis(2-hydroxy-3-methoxy-benzylidenehydrazine) as a co-crystalline compound",Iran J. Cryst. Miner26 (2018) 245-250. [DOI:10.29252/ijcm.26.1.245]
  41. [21] Zhang Y.Z., Ruan W.J., Zhao X.J.,Zhu Z.A.,"Synthesis and characterization of axialcoordination cobalt(III) complexes containing chiral Salen ligands", Polyhedron 22 (2003) 1535-1545. [DOI:10.1016/S0277-5387(03)00261-4]
  42. [21] Zhang Y.Z., Ruan W.J., Zhao X.J.,Zhu Z.A.,"Synthesis and characterization of axialcoordination cobalt(III) complexes containing chiral Salen ligands", Polyhedron 22 (2003) 1535-1545. [DOI:10.1016/S0277-5387(03)00261-4]
  43. [22] Percy G.C., Thorton D.A., "N-aryl salicylaldimine complexes: Infrared and PMR spectra of the ligands and vibrational frequencies of their metal(II) chelates",J.Inorg.Nucl.Chem34 (1972) 3357-3367. [DOI:10.1016/0022-1902(72)80230-6]
  44. [22] Percy G.C., Thorton D.A., "N-aryl salicylaldimine complexes: Infrared and PMR spectra of the ligands and vibrational frequencies of their metal(II) chelates",J.Inorg.Nucl.Chem34 (1972) 3357-3367. [DOI:10.1016/0022-1902(72)80230-6]
  45. [23] Khalaji A.D., Fejfarova K., Dusek M., "Crystal Structure of Schiff base Compound 2-[(2-chloro-4-nitrophenyl)iminomethyl] phenol",Iran J. Cryst. Miner22 (2015) 103-108.
  46. [23] Khalaji A.D., Fejfarova K., Dusek M., "Crystal Structure of Schiff base Compound 2-[(2-chloro-4-nitrophenyl)iminomethyl] phenol",Iran J. Cryst. Miner22 (2015) 103-108.
  47. [24] DehnoKhalaji A., Fejfarova K., Dusek M.,"Synthesis and crystal structure of Schiff-base compound (E)-4-methoxy-N-(4-hydroxybenzylidene) aniline", Iran J. Cryst. Miner21 (2013) 5-10.
  48. [24] DehnoKhalaji A., Fejfarova K., Dusek M.,"Synthesis and crystal structure of Schiff-base compound (E)-4-methoxy-N-(4-hydroxybenzylidene) aniline", Iran J. Cryst. Miner21 (2013) 5-10.
Iranian Journal of Crystallography and Mineralogy
Volume 28, Issue 3 - Serial Number 79
October 2020
Pages 789-796

Files

History

  • Receive Date: 20 October 2019
  • Revise Date: 23 January 2026
  • Accept Date: 17 February 2020

Share

How to cite

Statistics