Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases

Assoma Amon Benjamine; Koné Mawa; Alao Latifatou Laye; Bede Affoué Lucie; Koné Soleymane; N’Guessan Boka Robert; Bamba El Hadji Sawaliho; N’guessan Yao Thomas

doi:doi:10.11648/j.ijctc.20190701.17

Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases

Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, N’Guessan Boka Robert, Bamba El Hadji Sawaliho, N’guessan Yao Thomas

Published in International Journal of Computational and Theoretical Chemistry (Volume 7, Issue 1)

Received: 31 January 2019 Accepted: 15 March 2019 Published: 3 April 2019

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Abstract

This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.

Published in	International Journal of Computational and Theoretical Chemistry (Volume 7, Issue 1)
DOI	10.11648/j.ijctc.20190701.17
Page(s)	49-55
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), 2019. Published by Science Publishing Group

Keywords

2-Thioxanthine, Stability, Tautomerism, Acidity, B3LYP

References

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APA Style

Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. (2019). Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. International Journal of Computational and Theoretical Chemistry, 7(1), 49-55. https://doi.org/10.11648/j.ijctc.20190701.17

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ACS Style

Assoma Amon Benjamine; Koné Mawa; Alao Latifatou Laye; Bede Affoué Lucie; Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int. J. Comput. Theor. Chem. 2019, 7(1), 49-55. doi: 10.11648/j.ijctc.20190701.17

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AMA Style

Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int J Comput Theor Chem. 2019;7(1):49-55. doi: 10.11648/j.ijctc.20190701.17

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@article{10.11648/j.ijctc.20190701.17,
  author = {Assoma Amon Benjamine and Koné Mawa and Alao Latifatou Laye and Bede Affoué Lucie and Koné Soleymane and N’Guessan Boka Robert and Bamba El Hadji Sawaliho and N’guessan Yao Thomas},
  title = {Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases},
  journal = {International Journal of Computational and Theoretical Chemistry},
  volume = {7},
  number = {1},
  pages = {49-55},
  doi = {10.11648/j.ijctc.20190701.17},
  url = {https://doi.org/10.11648/j.ijctc.20190701.17},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijctc.20190701.17},
  abstract = {This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.},
 year = {2019}
}

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TY  - JOUR
T1  - Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases
AU  - Assoma Amon Benjamine
AU  - Koné Mawa
AU  - Alao Latifatou Laye
AU  - Bede Affoué Lucie
AU  - Koné Soleymane
AU  - N’Guessan Boka Robert
AU  - Bamba El Hadji Sawaliho
AU  - N’guessan Yao Thomas
Y1  - 2019/04/03
PY  - 2019
N1  - https://doi.org/10.11648/j.ijctc.20190701.17
DO  - 10.11648/j.ijctc.20190701.17
T2  - International Journal of Computational and Theoretical Chemistry
JF  - International Journal of Computational and Theoretical Chemistry
JO  - International Journal of Computational and Theoretical Chemistry
SP  - 49
EP  - 55
PB  - Science Publishing Group
SN  - 2376-7308
UR  - https://doi.org/10.11648/j.ijctc.20190701.17
AB  - This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.
VL  - 7
IS  - 1
ER  -

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Author Information

Assoma Amon Benjamine

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
Koné Mawa

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
Alao Latifatou Laye

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
Bede Affoué Lucie

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
Koné Soleymane

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
N’Guessan Boka Robert

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
Bamba El Hadji Sawaliho

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire
N’guessan Yao Thomas

Training and Research Unit of Sciences of Structures of Matter and Technology (UFR SSMT), Félix Houphou?t-Boigny University, Abidjan, C?te-d'Ivoire

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APA Style

Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. (2019). Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. International Journal of Computational and Theoretical Chemistry, 7(1), 49-55. https://doi.org/10.11648/j.ijctc.20190701.17

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ACS Style

Assoma Amon Benjamine; Koné Mawa; Alao Latifatou Laye; Bede Affoué Lucie; Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int. J. Comput. Theor. Chem. 2019, 7(1), 49-55. doi: 10.11648/j.ijctc.20190701.17

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AMA Style

Assoma Amon Benjamine, Koné Mawa, Alao Latifatou Laye, Bede Affoué Lucie, Koné Soleymane, et al. Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases. Int J Comput Theor Chem. 2019;7(1):49-55. doi: 10.11648/j.ijctc.20190701.17

Copy | Download

@article{10.11648/j.ijctc.20190701.17,
  author = {Assoma Amon Benjamine and Koné Mawa and Alao Latifatou Laye and Bede Affoué Lucie and Koné Soleymane and N’Guessan Boka Robert and Bamba El Hadji Sawaliho and N’guessan Yao Thomas},
  title = {Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases},
  journal = {International Journal of Computational and Theoretical Chemistry},
  volume = {7},
  number = {1},
  pages = {49-55},
  doi = {10.11648/j.ijctc.20190701.17},
  url = {https://doi.org/10.11648/j.ijctc.20190701.17},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijctc.20190701.17},
  abstract = {This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.},
 year = {2019}
}

Copy | Download

TY  - JOUR
T1  - Density Functional Theory (B3LYP/6-311+G(d, p)) Study of Stability, Tautomerism and Acidity of 2-Thioxanthine in Gas and Aqueous Phases
AU  - Assoma Amon Benjamine
AU  - Koné Mawa
AU  - Alao Latifatou Laye
AU  - Bede Affoué Lucie
AU  - Koné Soleymane
AU  - N’Guessan Boka Robert
AU  - Bamba El Hadji Sawaliho
AU  - N’guessan Yao Thomas
Y1  - 2019/04/03
PY  - 2019
N1  - https://doi.org/10.11648/j.ijctc.20190701.17
DO  - 10.11648/j.ijctc.20190701.17
T2  - International Journal of Computational and Theoretical Chemistry
JF  - International Journal of Computational and Theoretical Chemistry
JO  - International Journal of Computational and Theoretical Chemistry
SP  - 49
EP  - 55
PB  - Science Publishing Group
SN  - 2376-7308
UR  - https://doi.org/10.11648/j.ijctc.20190701.17
AB  - This work is a contribution of theoretical chemistry to the knowledge of 2‑thioxanthine's properties. Its aim first consists in checking the chemistry's results related to the exploitation of semi-empirical methods; it provides theoretical data on the acidity of 2‑thioxanthine tautomers. To do this, the DFT method with the B3LYP functional, associated with the 6‑311+G(d, p) basis set was used. The aqueous phase was modelled with the Polarizable Continuum Model (PCM). The results show that in gas and aqueous phases 2‑thioxanthine can exist as a mixture of four tautomers 2TX(1,3,7), 2TXX(1,3,9), 2TX(1,7,10) and 2TX(1,9,10). The relative stability decreases in the order 2TX(1,3,7)> 2TX(1,3,9)> 2TX(1,9,10)> 2TX(1,7,10). This work establishes that the tautomer 2TX(1,9,10) comes from the 2TX(1,3,7) via the 2TX(1,3,9) one. It demonstrates that the acidity of the most stable tautomer’s nitrogen 2TX(1,3,7), decreases in the order 7> 3> 1 in gas phase and in the order 3> 7>1 in aqueous phase. It provides data to elucidate the mechanisms to understand biological activities of 2‑thioxanthine.
VL  - 7
IS  - 1
ER  -

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