Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride

Aboubacar Diop; Tidiane Diop; Mouhamadou Sembene Boye; Dame Seye; Paul Tinnemans; Cheikh Abdoul Khadir Diop

doi:doi:10.11648/j.sjc.20241205.13

Research Article |

| Peer-Reviewed

Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride

Aboubacar Diop^*

, Tidiane Diop

, Mouhamadou Sembene Boye

, Dame Seye

, Paul Tinnemans

, Cheikh Abdoul Khadir Diop

Published in Science Journal of Chemistry (Volume 12, Issue 5)

Received: 7 August 2024 Accepted: 2 September 2024 Published: 20 September 2024

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

New Schiff base compound N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium)amine chloride obtained by a condensation reaction between 3,3’-iminidipropylamine (C₆H₁₇N₃) and 2,4-dichlorobenzaldehyde (C₇H₄Cl₂O) in 1:2 ratio in methanol. The compound is characterized by elemental analyze (CHN) and FT-IR (Fourier-transform infrared) spectroscopic technique which shows the presence of the imine group resulting from a condensation reaction and two potentiel donor sites. Crystal structure was obtained by single-crystal X-ray diffraction (RX). Compound crystallize in the orthorhombic system, space groupe Pnma with unit cell parameters: a = 7.0681(2) Å, b = 29,7679 (10) Å, c = 11.4545(4) Å, α =β =Ɣ = 90°, V = 2410.06 (14) Å³and Z = 4. Due to a mirror plane through the molecule, the asymmetric unit consists of only half the molecule. In the crystal structure of the compound, the dihedral angle formed between an aromatic ring C08/C06/C07/C10/C13/C09 and the aliphatic group C11/C15/C14/N04/C14/C15/C11 is equal to 77.42°. In addition, the aromatic rings are in the Trans position with the aliphatic group compared to the imine bonds C12-N05 and the angle formed around C12 is 120.78 (11)° whose is sufficient to maintain the cycles in Trans configuration. Thermogravimetric analysis (TG) of the compound shows very good thermal stability and decomposition from 180°C.

Published in	Science Journal of Chemistry (Volume 12, Issue 5)
DOI	10.11648/j.sjc.20241205.13
Page(s)	102-108
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Schiff Base, Crystal Structure, 3,3’-Iminidipropylamine, 2,4-Dichlorobenzaldeyde, Spectroscopic Technique, X-Ray Diffraction, Thermogravimetric Analysis

References

[1]	Schiff, H. (1864). A new series of organic bases. Ann. Chem. 131, 118. https://doi.org/10.1002/jlac.18641310113
[2]	Rudrapal, M. et Biplab, D. (2013). Chemistry and Biological Importance of Heterocyclic Schiff's Bases. International research journal of pure & applied chemistry., 3, 232-249. https://doi.org/10.9734/IRJPAC/2013/3996
[3]	Pervaiz, M., Yousaf, M., Ahmad, I. and Munawar, A. (2019). Synthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes. Spectrochimica Acta Part A, Molecular and biomolecular spectroscopy., 206, 642-649. https://doi.org/10.1016/j.saa.2018.05.057
[4]	El-ajaily, M., Maihub, A., Mahanta, U., Badhei, G., Mohapatra, R. P. and Dias. (2018). Mixed ligand complexes containing Schiff bases and their biological activities: a short review. Rasayan. J. Chem. 11, 166-174. http://dx.doi.org/10.7324/RJC.2018.1111988
[5]	Dalia, S., Afsan, F., Hossain, M., Khan, M., Zakaria, C. M., E-Zahan, M. and Ali, M. (2018). A short review on chemistry of schiff base metal complexes and their catalytic application. Int. J. Chem. Stud., 6, 2859-2866. https://doi.org/10.33545/2664844X
[6]	Neelakantana, M. A., Rusalraj, F., Dharmaraja, J., Johnsonraja, S., Jeyakumar, T. and Pillai, M. S. (2008). Spectral Characterization, Cyclic Voltammetry, Morphology, Biological Activities and DNA Cleaving Studies of Amino Acid Schiff Base Metal(II) Complexes. Spectrochimica Acta A, 71, 1599-1609. https://doi.org/10.1016/j.saa.2008.06.008
[7]	Mandal, S., Layek, M. et Saha, R. (2021). Synthesis, crystal structure and antibacterial activity of four mononuclear Schiff base complexes of copper(II) and nickel(II). Transit Met Chem., 46, 9-16. https://doi.org/10.1007/s11243-020-00416-6
[8]	Abbasi, Z., Salehi, M., Khaleghian, A. et Kubicki, M. (2018). New Cu(II), Mn(II) and Mn(III) Schiff base complexes cause noncovalent interactions: X-ray crystallography survey, Hirshfeld surface analysis and molecular simulation investigation against SARS-CoV-2. Journal of Molecular Structure., 06, 104. https://doi.org/10.1016/j.molstruc.2022.134857
[9]	Miloud, M. M. et El-ajaily., M. M. (2020). Antifungal Activity of Some Mixed Ligand Complexes Incorporating Schiff Bases. J Bacteriol Mycol., 7(1), 1122.
[10]	Uzzaman, M., Junaid, M. et Uddin, M. N. (2020). Evaluation of anti-tuberculosis activity of some oxotitanium(IV) Schiff base complexes; molecular docking, dynamics simulation and ADMET studies. SN Appl. Sci., 2, 880. https://doi.org/10.1007/s42452-020-2644-0
[11]	Şenocak, A., Taş, N. A., Taslimi, P., Tüzün, B., Aydin, A. et Karadağ, A. (2022). Novel amino acid Schiff base Zn(II) complexes as new therapeutic approaches in diabetes and Alzheimer's disease: Synthesis, characterization, biological evaluation, and molecular docking studies. J. Biochem. Mol. Toxicol., 36, 22969. https://doi.org/10.1002/jbt.22969
[12]	Munawar, K. S., Haroon, S. M., Hussain, S. A. et Raza, H. (2018). Schiff bases: Multipurpose pharmacophores with extensive biological applications., J. Basic Appl Sci., 14, 217-229. https://doi.org/10.6000/1927-5129.2018.14.34
[13]	Bruker, SAINT V8.38A. Bruker AXS Inc., Madison, Wisconsin, USA.
[14]	Krause, L., Herbst-Irmer, R., Sheldrick, G. M. and Stalke, D. (2015). Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. J. Appl. Cryst., 48, 3-10. https://doi.org/10.1107/S1600576714022985
[15]	Sheldrick, G. M. (2015). Acta Cryst., A71, 3–8. https://doi.org/10.1107/S2053273314026370
[16]	Sheldrick, G. M. (2015). Acta Cryst., C71, 3–8. http://dx.doi.org/10.1107/S2053229614024218
[17]	Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. and Puschmann, H. (2009). OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Cryst., 42, 339-341. https://doi.org/10.1107/S0021889808042726
[18]	Shmukler, L. E., Gruzdev, M. S., Kudryakova, N. O., Fadeeva, Y. A., Kolker, A. M. and Safonova, L. P. (2018). Triethylammonium-based protic ionic liquids with sulfonic acids: phase behavior and electrochemistry. J. Mol. Liq., 266, 139-146. https://doi.org/10.1016/J.MOLLIQ.2018.06.059
[19]	Mori K., Hashimoto, S., Yuzuri, T. and Sakakibara, K. (2010). Structural and spectroscopic characteristics of a proton-conductive Ionic liquid diethylmethylammonium trifluoromethanesulfonate [dema][TfOH]. Bull Chem. Soc. Jpn. 83(4), 328-334. https://doi.org/10.1246/bcsj.20090209
[20]	Spek, A. L. (2015). Acta Cryst. C71, 9-18. https://doi.org/10.1107/s2053229614024929
[21]	Melvin M. S., Calcutt M. W., Noftle R. E. and Manderville R. A. (2002). Influence of the A-Ring on the Redox and Nuclease Properties of the Prodigiosins: Importance of the Bipyrrole Moiety in Oxidative DNA Cleavag Chem. Res. Toxicol. 15, 742–748. https://doi.org/10.1021/tx025508p
[22]	Dehnokhalaji, A., Fejfarová, K., and Dušek, M. (2015). Crystal structure of schiff base compound 2- [(2-chloro-4-nitrophenyl) iminomethyl] phenol. J. Chem. Cryst. 41, 1515-1519.

Cite This Article

Plain Text BibTeX RIS

APA Style

Diop, A., Diop, T., Boye, M. S., Seye, D., Tinnemans, P., et al. (2024). Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Science Journal of Chemistry, 12(5), 102-108. https://doi.org/10.11648/j.sjc.20241205.13

Copy | Download

ACS Style

Diop, A.; Diop, T.; Boye, M. S.; Seye, D.; Tinnemans, P., et al. Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Sci. J. Chem. 2024, 12(5), 102-108. doi: 10.11648/j.sjc.20241205.13

Copy | Download

AMA Style

Diop A, Diop T, Boye MS, Seye D, Tinnemans P, et al. Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Sci J Chem. 2024;12(5):102-108. doi: 10.11648/j.sjc.20241205.13

Copy | Download

@article{10.11648/j.sjc.20241205.13,
  author = {Aboubacar Diop and Tidiane Diop and Mouhamadou Sembene Boye and Dame Seye and Paul Tinnemans and Cheikh Abdoul Khadir Diop},
  title = {Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride
},
  journal = {Science Journal of Chemistry},
  volume = {12},
  number = {5},
  pages = {102-108},
  doi = {10.11648/j.sjc.20241205.13},
  url = {https://doi.org/10.11648/j.sjc.20241205.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20241205.13},
  abstract = {New Schiff base compound N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium)amine chloride obtained by a condensation reaction between 3,3’-iminidipropylamine (C6H17N3) and 2,4-dichlorobenzaldehyde (C7H4Cl2O) in 1:2 ratio in methanol. The compound is characterized by elemental analyze (CHN) and FT-IR (Fourier-transform infrared) spectroscopic technique which shows the presence of the imine group resulting from a condensation reaction and two potentiel donor sites. Crystal structure was obtained by single-crystal X-ray diffraction (RX). Compound crystallize in the orthorhombic system, space groupe Pnma with unit cell parameters: a = 7.0681(2) Å, b = 29,7679 (10) Å, c = 11.4545(4) Å, α =β =Ɣ = 90°, V = 2410.06 (14) Å3 and Z = 4. Due to a mirror plane through the molecule, the asymmetric unit consists of only half the molecule. In the crystal structure of the compound, the dihedral angle formed between an aromatic ring C08/C06/C07/C10/C13/C09 and the aliphatic group C11/C15/C14/N04/C14/C15/C11 is equal to 77.42°. In addition, the aromatic rings are in the Trans position with the aliphatic group compared to the imine bonds C12-N05 and the angle formed around C12 is 120.78 (11)° whose is sufficient to maintain the cycles in Trans configuration. Thermogravimetric analysis (TG) of the compound shows very good thermal stability and decomposition from 180°C.
},
 year = {2024}
}

Copy | Download

TY  - JOUR
T1  - Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride

AU  - Aboubacar Diop
AU  - Tidiane Diop
AU  - Mouhamadou Sembene Boye
AU  - Dame Seye
AU  - Paul Tinnemans
AU  - Cheikh Abdoul Khadir Diop
Y1  - 2024/09/20
PY  - 2024
N1  - https://doi.org/10.11648/j.sjc.20241205.13
DO  - 10.11648/j.sjc.20241205.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 102
EP  - 108
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20241205.13
AB  - New Schiff base compound N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium)amine chloride obtained by a condensation reaction between 3,3’-iminidipropylamine (C6H17N3) and 2,4-dichlorobenzaldehyde (C7H4Cl2O) in 1:2 ratio in methanol. The compound is characterized by elemental analyze (CHN) and FT-IR (Fourier-transform infrared) spectroscopic technique which shows the presence of the imine group resulting from a condensation reaction and two potentiel donor sites. Crystal structure was obtained by single-crystal X-ray diffraction (RX). Compound crystallize in the orthorhombic system, space groupe Pnma with unit cell parameters: a = 7.0681(2) Å, b = 29,7679 (10) Å, c = 11.4545(4) Å, α =β =Ɣ = 90°, V = 2410.06 (14) Å3 and Z = 4. Due to a mirror plane through the molecule, the asymmetric unit consists of only half the molecule. In the crystal structure of the compound, the dihedral angle formed between an aromatic ring C08/C06/C07/C10/C13/C09 and the aliphatic group C11/C15/C14/N04/C14/C15/C11 is equal to 77.42°. In addition, the aromatic rings are in the Trans position with the aliphatic group compared to the imine bonds C12-N05 and the angle formed around C12 is 120.78 (11)° whose is sufficient to maintain the cycles in Trans configuration. Thermogravimetric analysis (TG) of the compound shows very good thermal stability and decomposition from 180°C.

VL  - 12
IS  - 5
ER  -

Copy | Download

Author Information

Aboubacar Diop

Department of Chemistry, Faculty of Science and Technology Cheikh Anta Diop University, Dakar, Senegal

Contact Email

http://orcid.org/0000-0002-9537-7921
Tidiane Diop

Department of Chemistry, Faculty of Science and Technology Cheikh Anta Diop University, Dakar, Senegal

Contact Email

http://orcid.org/0000-0003-1098-451X
Mouhamadou Sembene Boye

Department of Physics and Chemistry, Faculty of Education and Training Sciences and Technologies, Dakar, Senegal

Contact Email

http://orcid.org/0009-0000-8447-6409
Dame Seye

Department of Physics-Chemistry, UFR Science and Technology, Iba Der Thiam, Thies, Senegal

Contact Email

http://orcid.org/0009-0009-9431-1793
Paul Tinnemans

Institute for Molecules and Materials (IMM) Solid State Chemistry, Faculty of Science Radboud University, Nijmegen, Netherlands

Contact Email

http://orcid.org/0000-0002-3930-7056
Cheikh Abdoul Khadir Diop

Department of Chemistry, Faculty of Science and Technology Cheikh Anta Diop University, Dakar, Senegal

Contact Email

http://orcid.org/0000-0003-0001-9484

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Diop, A., Diop, T., Boye, M. S., Seye, D., Tinnemans, P., et al. (2024). Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Science Journal of Chemistry, 12(5), 102-108. https://doi.org/10.11648/j.sjc.20241205.13

Copy | Download

ACS Style

Diop, A.; Diop, T.; Boye, M. S.; Seye, D.; Tinnemans, P., et al. Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Sci. J. Chem. 2024, 12(5), 102-108. doi: 10.11648/j.sjc.20241205.13

Copy | Download

AMA Style

Diop A, Diop T, Boye MS, Seye D, Tinnemans P, et al. Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride. Sci J Chem. 2024;12(5):102-108. doi: 10.11648/j.sjc.20241205.13

Copy | Download

@article{10.11648/j.sjc.20241205.13,
  author = {Aboubacar Diop and Tidiane Diop and Mouhamadou Sembene Boye and Dame Seye and Paul Tinnemans and Cheikh Abdoul Khadir Diop},
  title = {Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride
},
  journal = {Science Journal of Chemistry},
  volume = {12},
  number = {5},
  pages = {102-108},
  doi = {10.11648/j.sjc.20241205.13},
  url = {https://doi.org/10.11648/j.sjc.20241205.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20241205.13},
  abstract = {New Schiff base compound N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium)amine chloride obtained by a condensation reaction between 3,3’-iminidipropylamine (C6H17N3) and 2,4-dichlorobenzaldehyde (C7H4Cl2O) in 1:2 ratio in methanol. The compound is characterized by elemental analyze (CHN) and FT-IR (Fourier-transform infrared) spectroscopic technique which shows the presence of the imine group resulting from a condensation reaction and two potentiel donor sites. Crystal structure was obtained by single-crystal X-ray diffraction (RX). Compound crystallize in the orthorhombic system, space groupe Pnma with unit cell parameters: a = 7.0681(2) Å, b = 29,7679 (10) Å, c = 11.4545(4) Å, α =β =Ɣ = 90°, V = 2410.06 (14) Å3 and Z = 4. Due to a mirror plane through the molecule, the asymmetric unit consists of only half the molecule. In the crystal structure of the compound, the dihedral angle formed between an aromatic ring C08/C06/C07/C10/C13/C09 and the aliphatic group C11/C15/C14/N04/C14/C15/C11 is equal to 77.42°. In addition, the aromatic rings are in the Trans position with the aliphatic group compared to the imine bonds C12-N05 and the angle formed around C12 is 120.78 (11)° whose is sufficient to maintain the cycles in Trans configuration. Thermogravimetric analysis (TG) of the compound shows very good thermal stability and decomposition from 180°C.
},
 year = {2024}
}

Copy | Download

TY  - JOUR
T1  - Synthesis, Crystal Structure and Thermal Stability of the Schiff Base N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium) Amine Chloride

AU  - Aboubacar Diop
AU  - Tidiane Diop
AU  - Mouhamadou Sembene Boye
AU  - Dame Seye
AU  - Paul Tinnemans
AU  - Cheikh Abdoul Khadir Diop
Y1  - 2024/09/20
PY  - 2024
N1  - https://doi.org/10.11648/j.sjc.20241205.13
DO  - 10.11648/j.sjc.20241205.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 102
EP  - 108
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20241205.13
AB  - New Schiff base compound N,N'-bis(2,4-dichlorobenzylidene-3-propylammonium)amine chloride obtained by a condensation reaction between 3,3’-iminidipropylamine (C6H17N3) and 2,4-dichlorobenzaldehyde (C7H4Cl2O) in 1:2 ratio in methanol. The compound is characterized by elemental analyze (CHN) and FT-IR (Fourier-transform infrared) spectroscopic technique which shows the presence of the imine group resulting from a condensation reaction and two potentiel donor sites. Crystal structure was obtained by single-crystal X-ray diffraction (RX). Compound crystallize in the orthorhombic system, space groupe Pnma with unit cell parameters: a = 7.0681(2) Å, b = 29,7679 (10) Å, c = 11.4545(4) Å, α =β =Ɣ = 90°, V = 2410.06 (14) Å3 and Z = 4. Due to a mirror plane through the molecule, the asymmetric unit consists of only half the molecule. In the crystal structure of the compound, the dihedral angle formed between an aromatic ring C08/C06/C07/C10/C13/C09 and the aliphatic group C11/C15/C14/N04/C14/C15/C11 is equal to 77.42°. In addition, the aromatic rings are in the Trans position with the aliphatic group compared to the imine bonds C12-N05 and the angle formed around C12 is 120.78 (11)° whose is sufficient to maintain the cycles in Trans configuration. Thermogravimetric analysis (TG) of the compound shows very good thermal stability and decomposition from 180°C.

VL  - 12
IS  - 5
ER  -

Copy | Download