Theoretical studies on the tautomerism of tetrazole selenone

Alireza Najafi Chermhini, Mostafa Abedi, Hossein Farrokhpour, Abbas Teimouri, Bahareh Reisi

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The tautomerism of all possible forms of tetrazole selenone (A-G), induced by proton transfer, was studied, theoretically, in different environments including gas phase, continuum solvent and microsolvated environment with one or two explicit water or ammonia molecules. The calculations were performed using two different levels of theory including mPW2PLYP and DFT-B3LYP. The 6-311++G(d,p) basis set was used for C, H, O and N and the standard relativistic effective core pseudo potential LANL2DZ basis set was used for Se atom. It was found that the tetrazole selenone, in the form of A, is the most stable isomer in all of the environments considered in this work. The kinetics of proton transfer reaction was studied in both gas and solvent environments and it was concluded that the activation energy of the reaction increases with going from the gas phase to polar solvents. Moreover, the proton transfer reaction assisted by one or two water or ammonia molecules was investigated and it was found that the activation energy significantly reduces.
Original languageEnglish
JournalJournal of Molecular Modeling
Volume19
Issue number10
Pages (from-to)4377-4386
Number of pages10
ISSN1610-2940
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • Imidazole selenone
  • Microsolvation
  • mPW2PLYP
  • Solvent effect
  • Tautomerism

Cite this

Chermhini, Alireza Najafi ; Abedi, Mostafa ; Farrokhpour, Hossein ; Teimouri, Abbas ; Reisi, Bahareh. / Theoretical studies on the tautomerism of tetrazole selenone. In: Journal of Molecular Modeling. 2013 ; Vol. 19, No. 10. pp. 4377-4386.
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title = "Theoretical studies on the tautomerism of tetrazole selenone",
abstract = "The tautomerism of all possible forms of tetrazole selenone (A-G), induced by proton transfer, was studied, theoretically, in different environments including gas phase, continuum solvent and microsolvated environment with one or two explicit water or ammonia molecules. The calculations were performed using two different levels of theory including mPW2PLYP and DFT-B3LYP. The 6-311++G(d,p) basis set was used for C, H, O and N and the standard relativistic effective core pseudo potential LANL2DZ basis set was used for Se atom. It was found that the tetrazole selenone, in the form of A, is the most stable isomer in all of the environments considered in this work. The kinetics of proton transfer reaction was studied in both gas and solvent environments and it was concluded that the activation energy of the reaction increases with going from the gas phase to polar solvents. Moreover, the proton transfer reaction assisted by one or two water or ammonia molecules was investigated and it was found that the activation energy significantly reduces.",
keywords = "Imidazole selenone, Microsolvation, mPW2PLYP, Solvent effect, Tautomerism",
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year = "2013",
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Chermhini, AN, Abedi, M, Farrokhpour, H, Teimouri, A & Reisi, B 2013, 'Theoretical studies on the tautomerism of tetrazole selenone', Journal of Molecular Modeling, vol. 19, no. 10, pp. 4377-4386. https://doi.org/10.1007/s00894-013-1941-6

Theoretical studies on the tautomerism of tetrazole selenone. / Chermhini, Alireza Najafi; Abedi, Mostafa; Farrokhpour, Hossein; Teimouri, Abbas; Reisi, Bahareh.

In: Journal of Molecular Modeling, Vol. 19, No. 10, 2013, p. 4377-4386.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Theoretical studies on the tautomerism of tetrazole selenone

AU - Chermhini, Alireza Najafi

AU - Abedi, Mostafa

AU - Farrokhpour, Hossein

AU - Teimouri, Abbas

AU - Reisi, Bahareh

PY - 2013

Y1 - 2013

N2 - The tautomerism of all possible forms of tetrazole selenone (A-G), induced by proton transfer, was studied, theoretically, in different environments including gas phase, continuum solvent and microsolvated environment with one or two explicit water or ammonia molecules. The calculations were performed using two different levels of theory including mPW2PLYP and DFT-B3LYP. The 6-311++G(d,p) basis set was used for C, H, O and N and the standard relativistic effective core pseudo potential LANL2DZ basis set was used for Se atom. It was found that the tetrazole selenone, in the form of A, is the most stable isomer in all of the environments considered in this work. The kinetics of proton transfer reaction was studied in both gas and solvent environments and it was concluded that the activation energy of the reaction increases with going from the gas phase to polar solvents. Moreover, the proton transfer reaction assisted by one or two water or ammonia molecules was investigated and it was found that the activation energy significantly reduces.

AB - The tautomerism of all possible forms of tetrazole selenone (A-G), induced by proton transfer, was studied, theoretically, in different environments including gas phase, continuum solvent and microsolvated environment with one or two explicit water or ammonia molecules. The calculations were performed using two different levels of theory including mPW2PLYP and DFT-B3LYP. The 6-311++G(d,p) basis set was used for C, H, O and N and the standard relativistic effective core pseudo potential LANL2DZ basis set was used for Se atom. It was found that the tetrazole selenone, in the form of A, is the most stable isomer in all of the environments considered in this work. The kinetics of proton transfer reaction was studied in both gas and solvent environments and it was concluded that the activation energy of the reaction increases with going from the gas phase to polar solvents. Moreover, the proton transfer reaction assisted by one or two water or ammonia molecules was investigated and it was found that the activation energy significantly reduces.

KW - Imidazole selenone

KW - Microsolvation

KW - mPW2PLYP

KW - Solvent effect

KW - Tautomerism

U2 - 10.1007/s00894-013-1941-6

DO - 10.1007/s00894-013-1941-6

M3 - Journal article

VL - 19

SP - 4377

EP - 4386

JO - Journal of Molecular Modeling

JF - Journal of Molecular Modeling

SN - 1610-2940

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ER -