Research Article
BibTex RIS Cite
Year 2019, Volume: 6 Issue: 2, 189 - 200, 15.06.2019
https://doi.org/10.18596/jotcsa.483143

Abstract

References

  • 1. Schiff H. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen. Justus Liebigs Annalen der Chemie. 1864;131:118–9.
  • 2. Arulmurugan S, Kavitha HP, Venkatraman BR. Biological activities of Schiff base and its complexes: a review. Rasayan J. Chem, 2010;3:385-410.
  • 3. Behpour M, Ghoreishi SM, Mohammadi N, Soltani N, Salavati-Niasari M. Investigation of some Schiff base compounds containing disulfide bond as HCl corrosion inhibitors for mild steel. Corros. Sci. 2010;52:4046–57.
  • 4. Cozzi PG. Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 2004;33:410-21.
  • 5. Anis I, Aslam M, Noreen Z, Afza N, Hussain A, Safder M, Chaudhry AH. A Review (part a)-General Applications of Schiff Base Transition Metal Complexes. Int. J. Cur. Pharm. Res. 2013;5:21-4.
  • 6. Gupta KC, Sutar AK. Catalytic activities of Schiff base transition metal complexes. Coord. Chem. Rev. 2008;252:1420–50.
  • 7. Anis I, Aslam M, Afza N, Iqbal L, Noreen Z, Hussain A, Safder M. A review (part c)-an overview of biological activities of schiff base transition metal complexes. Int. J. Cur. Pharm. Res. 2013;5:48-57.
  • 8. Kumar S, Nath DD, Saxena PN. Applications of metal complexes of Schiff bases-A Review. J. Sci. Ind. Res. 2009;68:181-7.
  • 9. Dekar S, Ouari K, Bendia S, Hannachi D, Weiss J. Mononuclear oxovanadium(IV) Schiff base complex: Synthesis, spectroscopy, electrochemistry, DFT calculation and catalytic activity. J. of Organometal. Chem. 2018;866:165-76.
  • 10. Ding R, Wang Q, Wen X. 6,6-Di-tert-butyl-4,4-dimethyl-2,2-(1,2-phenylenebis(nitrilomethanylylidene)) Diphenol. Acta Cryst. 2012;E68:40.
  • 11. Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals. Pergamon Press, New York;2013.
  • 12. Larrow JF, Jacobsen EN. A Practical Method for the Large-Scale Preparation of (N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-))manganese(III) chloride, a Highly Enantioselective Epoxidation Catalyst. J. Org. Chem. 1994;59:1939-42.
  • 13. Stoe and Cie. X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany, 2002.
  • 14. Sheldrick GM. SHELXT – Integrated space-group and crystal-structure determination. Acta Cryst. 2015;A71:3-8.
  • 15. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Cryst. 2015;C71:3-8.
  • 16. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, Streek J. Mercury: visualization and analysis of crystal structures. J. Appl. Cryst. 2006;39:453-7.
  • 17. Farrugia LJ. WinGX and ORTEP for Windows: an update. J. Appl. Cryst. 2012;32:837.
  • 18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford;2004.
  • 19. Aihara, J-i. Reduced HOMO-LUMO Gap as an Index of Kinetic Stability for Polycyclic Aromatic Hydrocarbons. J. Phys. Chem. A 1999; 103:7487-95.
  • 20. Demircioglu Z, Albayrak C, Buyukgungor O. Experimental (X-ray, FT-IR and UV–vis spectra) and theoretical methods (DFT study) of (E)-3-methoxy-2-((p-tolylimino) methyl) phenol. Spect. Acta. Part A, 2014;128:748–58.
  • 21. Ersanli CC, Kantar GK, Şaşmaz S. Crystallographic, spectroscopic (FTIR and NMR) and quantum computational calculation studies on bis(2-methoxy-4-((E)-prop-1-enyl)phenyl)oxalate. J. Mol. Struct. 2017;1143: 318-27.
  • 22. Asiri AM, Ersanlı CC, Şahin O, Arshad MN, Hameed SA. Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro(benzo(f)chromene-3,2′-indoline. J. Mol. Struct. 2016;1111:108-17.
  • 23. Kansız S, Dege N. Synthesis, crystallographic structure, DFT calculations and Hirshfeld surface analysis of a fumarate bridged Co(II) coordination polymer. J. Mol. Struct. 2018;1173:42-51.
  • 24. Gümüş MK, Kansız S, Aydemir E, Gorobets NY, Dege N. Structural features of 7-methoxy-5-methyl-2-(pyridin-3-yl)-11,12-dihydro-5,11-methano(1,2,4)triazolo(1,5-c)(1,3,5)benzoxadiazocine: Experimental and theoretical (HF and DFT) studies, surface properties (MEP, Hirshfeld). J. Mol. Struct. 2018;1168:280-90.
  • 25. Sen F, Kansiz S, Ucar I. A one-dimensional copper(II) coordination polymer incorporating succinate and N,N-di­ethyl­ethyl­ene­di­amine ligands: crystallographic analysis, vibrational and surface features, and DFT analysis. Acta Cryst. 2017;C73:517-5242017.
  • 26. Turner MJ, MacKinnon JJ, Wolff SK, Grimwood DJ, Spackman PR, Jayatilaka D, Spackma MA. Crystal Explorer Ver. 17.5. University of Western Australia, Perth;2017.
  • 27. Kansiz S, Malinkin S, Dege N. Synthesis, Crystal structure and Hirshfeld surface analysis of tetraaquabis(isonicotinamide-κN1)cobalt(II) succinate. Acta Cryst. 2018;E74:1026-29.
  • 28. Kansiz S, Almarhoon ZM, Dege N. Synthesis, crystal structure and Hirshfeld surface analysis of tetraaquabis (isonicotinamide-κN1) cobalt (II) fumarate. Acta Cryst. 2018;E74:217-20.
  • 29. Aydemir E, Kansiz S, Gumus MK, Gorobets NY, Dege N. Crystal structure and Hirshfeld surface analysis of 7-ethoxy-5-methyl-2-(pyridin-3-yl)-11, 12-dihydro-5, 11-methano (1, 2, 4) triazolo (1, 5-c)(1, 3, 5) benzoxadiazocine. Acta Cryst. 2018;E74:367-70. 30. Sen P, Kansiz S, Dege N, Iskenderov TS, Yildiz SZ. Crystal structure and Hirshfeld surface analysis of 4-(4-(1H-benzo(d)imidazol-2-yl)phenoxy)phthalonitrile monohydrate Acta Cryst. 2018;E74:994-7.
  • 31. Sen P, Kansiz S, Golenya IA, Dege N. Crystal structure and Hirshfeld surface analysis of N, N′-bis (3-tert-butyl-2-hydroxy-5-methylbenzylidene) ethane-1, 2-diamine. Acta Cryst. 2018;E74:1147-50.

Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6'-((1E,1'E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol)

Year 2019, Volume: 6 Issue: 2, 189 - 200, 15.06.2019
https://doi.org/10.18596/jotcsa.483143

Abstract

Schiff bases have been used in biological processes and as chelating agents for several
decades.
This work presents the synthesis and
characterization of compound,
N,N’-Bis(3-tert-Butyl-5-methylsalicylidene)-1,2-diamino
phenylene as the Schiff base derivative with the reaction of an aromatic aldehyde derivative and o-phenylenediamine. The spectroscopic properties of the compound were
examined by FT-IR, 1H NMR, 13C NMR,  MS and elemental analyses. The molecular structure of the compound was also confirmed
using X-ray single-crystal data. And also theoretical calculations were obtained
by using Density Functional Theory (DFT) methods. The structural parameters
were
calculated by using DFT/B3LYP/6-31G(d,p) basis set in ground state. Molecular
Electrostatic Potential (MEP) map and the frontier molecular orbitals (HOMO-LUMO) of the compound were created by using the optimized structures. The
results of theoretical study using the DFT method at the B3LYP/6–31G(d,p) level
are in good agreement with the experimental data. Hirshfeld surface analyses and
two dimensional fingerprint plots were used to analyse the intermolecular
interactions present in the crystal, indicating that the most important
contributions for the crystal packing are from H∙∙∙H
(71.2%), H∙∙∙C/C∙∙∙H (18.7%), C∙∙∙C (4.8%) and H∙∙∙N/N∙∙∙H
(2.7%) interactions.

References

  • 1. Schiff H. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen. Justus Liebigs Annalen der Chemie. 1864;131:118–9.
  • 2. Arulmurugan S, Kavitha HP, Venkatraman BR. Biological activities of Schiff base and its complexes: a review. Rasayan J. Chem, 2010;3:385-410.
  • 3. Behpour M, Ghoreishi SM, Mohammadi N, Soltani N, Salavati-Niasari M. Investigation of some Schiff base compounds containing disulfide bond as HCl corrosion inhibitors for mild steel. Corros. Sci. 2010;52:4046–57.
  • 4. Cozzi PG. Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 2004;33:410-21.
  • 5. Anis I, Aslam M, Noreen Z, Afza N, Hussain A, Safder M, Chaudhry AH. A Review (part a)-General Applications of Schiff Base Transition Metal Complexes. Int. J. Cur. Pharm. Res. 2013;5:21-4.
  • 6. Gupta KC, Sutar AK. Catalytic activities of Schiff base transition metal complexes. Coord. Chem. Rev. 2008;252:1420–50.
  • 7. Anis I, Aslam M, Afza N, Iqbal L, Noreen Z, Hussain A, Safder M. A review (part c)-an overview of biological activities of schiff base transition metal complexes. Int. J. Cur. Pharm. Res. 2013;5:48-57.
  • 8. Kumar S, Nath DD, Saxena PN. Applications of metal complexes of Schiff bases-A Review. J. Sci. Ind. Res. 2009;68:181-7.
  • 9. Dekar S, Ouari K, Bendia S, Hannachi D, Weiss J. Mononuclear oxovanadium(IV) Schiff base complex: Synthesis, spectroscopy, electrochemistry, DFT calculation and catalytic activity. J. of Organometal. Chem. 2018;866:165-76.
  • 10. Ding R, Wang Q, Wen X. 6,6-Di-tert-butyl-4,4-dimethyl-2,2-(1,2-phenylenebis(nitrilomethanylylidene)) Diphenol. Acta Cryst. 2012;E68:40.
  • 11. Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals. Pergamon Press, New York;2013.
  • 12. Larrow JF, Jacobsen EN. A Practical Method for the Large-Scale Preparation of (N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-))manganese(III) chloride, a Highly Enantioselective Epoxidation Catalyst. J. Org. Chem. 1994;59:1939-42.
  • 13. Stoe and Cie. X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany, 2002.
  • 14. Sheldrick GM. SHELXT – Integrated space-group and crystal-structure determination. Acta Cryst. 2015;A71:3-8.
  • 15. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Cryst. 2015;C71:3-8.
  • 16. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, Streek J. Mercury: visualization and analysis of crystal structures. J. Appl. Cryst. 2006;39:453-7.
  • 17. Farrugia LJ. WinGX and ORTEP for Windows: an update. J. Appl. Cryst. 2012;32:837.
  • 18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford;2004.
  • 19. Aihara, J-i. Reduced HOMO-LUMO Gap as an Index of Kinetic Stability for Polycyclic Aromatic Hydrocarbons. J. Phys. Chem. A 1999; 103:7487-95.
  • 20. Demircioglu Z, Albayrak C, Buyukgungor O. Experimental (X-ray, FT-IR and UV–vis spectra) and theoretical methods (DFT study) of (E)-3-methoxy-2-((p-tolylimino) methyl) phenol. Spect. Acta. Part A, 2014;128:748–58.
  • 21. Ersanli CC, Kantar GK, Şaşmaz S. Crystallographic, spectroscopic (FTIR and NMR) and quantum computational calculation studies on bis(2-methoxy-4-((E)-prop-1-enyl)phenyl)oxalate. J. Mol. Struct. 2017;1143: 318-27.
  • 22. Asiri AM, Ersanlı CC, Şahin O, Arshad MN, Hameed SA. Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro(benzo(f)chromene-3,2′-indoline. J. Mol. Struct. 2016;1111:108-17.
  • 23. Kansız S, Dege N. Synthesis, crystallographic structure, DFT calculations and Hirshfeld surface analysis of a fumarate bridged Co(II) coordination polymer. J. Mol. Struct. 2018;1173:42-51.
  • 24. Gümüş MK, Kansız S, Aydemir E, Gorobets NY, Dege N. Structural features of 7-methoxy-5-methyl-2-(pyridin-3-yl)-11,12-dihydro-5,11-methano(1,2,4)triazolo(1,5-c)(1,3,5)benzoxadiazocine: Experimental and theoretical (HF and DFT) studies, surface properties (MEP, Hirshfeld). J. Mol. Struct. 2018;1168:280-90.
  • 25. Sen F, Kansiz S, Ucar I. A one-dimensional copper(II) coordination polymer incorporating succinate and N,N-di­ethyl­ethyl­ene­di­amine ligands: crystallographic analysis, vibrational and surface features, and DFT analysis. Acta Cryst. 2017;C73:517-5242017.
  • 26. Turner MJ, MacKinnon JJ, Wolff SK, Grimwood DJ, Spackman PR, Jayatilaka D, Spackma MA. Crystal Explorer Ver. 17.5. University of Western Australia, Perth;2017.
  • 27. Kansiz S, Malinkin S, Dege N. Synthesis, Crystal structure and Hirshfeld surface analysis of tetraaquabis(isonicotinamide-κN1)cobalt(II) succinate. Acta Cryst. 2018;E74:1026-29.
  • 28. Kansiz S, Almarhoon ZM, Dege N. Synthesis, crystal structure and Hirshfeld surface analysis of tetraaquabis (isonicotinamide-κN1) cobalt (II) fumarate. Acta Cryst. 2018;E74:217-20.
  • 29. Aydemir E, Kansiz S, Gumus MK, Gorobets NY, Dege N. Crystal structure and Hirshfeld surface analysis of 7-ethoxy-5-methyl-2-(pyridin-3-yl)-11, 12-dihydro-5, 11-methano (1, 2, 4) triazolo (1, 5-c)(1, 3, 5) benzoxadiazocine. Acta Cryst. 2018;E74:367-70. 30. Sen P, Kansiz S, Dege N, Iskenderov TS, Yildiz SZ. Crystal structure and Hirshfeld surface analysis of 4-(4-(1H-benzo(d)imidazol-2-yl)phenoxy)phthalonitrile monohydrate Acta Cryst. 2018;E74:994-7.
  • 31. Sen P, Kansiz S, Golenya IA, Dege N. Crystal structure and Hirshfeld surface analysis of N, N′-bis (3-tert-butyl-2-hydroxy-5-methylbenzylidene) ethane-1, 2-diamine. Acta Cryst. 2018;E74:1147-50.
There are 30 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Pınar Şen 0000-0002-3181-9890

Sevgi Kansız 0000-0002-8433-7975

Necmi Dege 0000-0003-0660-4721

Publication Date June 15, 2019
Submission Date November 15, 2018
Acceptance Date April 8, 2019
Published in Issue Year 2019 Volume: 6 Issue: 2

Cite

Vancouver Şen P, Kansız S, Dege N. Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6’-((1E,1’E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol). JOTCSA. 2019;6(2):189-200.