Theoretical study of the ionization potential of thymine: Effect of adding conjugated functional groups

Manuel Vega-Arroyo; Pierre R. LeBreton; Tijana Rajh; Peter Zapol; Larry A. Curtiss

doi:10.1016/j.cplett.2003.08.072

Theoretical study of the ionization potential of thymine: Effect of adding conjugated functional groups

Manuel Vega-Arroyo
, Pierre R. LeBreton
, Tijana Rajh
, Peter Zapol
, Larry A. Curtiss

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The ionization potential of thymine functionalized at the C5 position with the truncated linker groups, -CH=CHCO₂CH₃ and -CH=CHCONHCH₃, was examined using density functional theory. Results indicate that the addition of the carboxyl group to thymine lowers the adiabatic ionization potential by 0.4 eV. Further, modification of the carboxyl group by an amino group lowers the ionization potential by another 0.2 eV. The effect of solvation and base pairing with adenine on the modified thymine ionization energies was also investigated. The results provide evidence that linker groups can dampen the influence of adenine base pairing on thymine charge transfer.

Original language	English (US)
Pages (from-to)	54-62
Number of pages	9
Journal	Chemical Physics Letters
Volume	380
Issue number	1-2
DOIs	https://doi.org/10.1016/j.cplett.2003.08.072
State	Published - Oct 13 2003
Externally published	Yes

ASJC Scopus subject areas

General Physics and Astronomy
Physical and Theoretical Chemistry

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10.1016/j.cplett.2003.08.072

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@article{0f0bea5ab92c4a6b87b6b54adf70423f,

title = "Theoretical study of the ionization potential of thymine: Effect of adding conjugated functional groups",

abstract = "The ionization potential of thymine functionalized at the C5 position with the truncated linker groups, -CH=CHCO2CH3 and -CH=CHCONHCH3, was examined using density functional theory. Results indicate that the addition of the carboxyl group to thymine lowers the adiabatic ionization potential by 0.4 eV. Further, modification of the carboxyl group by an amino group lowers the ionization potential by another 0.2 eV. The effect of solvation and base pairing with adenine on the modified thymine ionization energies was also investigated. The results provide evidence that linker groups can dampen the influence of adenine base pairing on thymine charge transfer.",

author = "Manuel Vega-Arroyo and LeBreton, \{Pierre R.\} and Tijana Rajh and Peter Zapol and Curtiss, \{Larry A.\}",

note = "Funding Information: This work was supported by the US Department of Energy{\textquoteright}s Office of Basic Energy Sciences, Division of Chemical Sciences, under contract no. W-31-109-ENG-38. Manuel Vega-Arroyo also acknowledges support from the Division of Educational Programs at Argonne National Laboratory. Funding Information: The submitted manuscript has been created by the University of Chicago as Operator of Argonne National Laboratory ({\textquoteleft}Argonne{\textquoteright}) under Contract No. W-31-109-ENG-38 with the US Department of Energy. The US Government retains for itself, and others acting on its behalf, a paid-up, nonexclusive, irrevocable worldwide license in said article to reproduce, prepare derivative works, distribute copies to the public, and perform publicly and display publicly, by or on behalf of the Government. ",

year = "2003",

month = oct,

day = "13",

doi = "10.1016/j.cplett.2003.08.072",

language = "English (US)",

volume = "380",

pages = "54--62",

journal = "Chemical Physics Letters",

issn = "0009-2614",

publisher = "Elsevier B.V.",

number = "1-2",

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TY - JOUR

T1 - Theoretical study of the ionization potential of thymine

T2 - Effect of adding conjugated functional groups

AU - Vega-Arroyo, Manuel

AU - LeBreton, Pierre R.

AU - Rajh, Tijana

AU - Zapol, Peter

AU - Curtiss, Larry A.

N1 - Funding Information: This work was supported by the US Department of Energy’s Office of Basic Energy Sciences, Division of Chemical Sciences, under contract no. W-31-109-ENG-38. Manuel Vega-Arroyo also acknowledges support from the Division of Educational Programs at Argonne National Laboratory. Funding Information: The submitted manuscript has been created by the University of Chicago as Operator of Argonne National Laboratory (‘Argonne’) under Contract No. W-31-109-ENG-38 with the US Department of Energy. The US Government retains for itself, and others acting on its behalf, a paid-up, nonexclusive, irrevocable worldwide license in said article to reproduce, prepare derivative works, distribute copies to the public, and perform publicly and display publicly, by or on behalf of the Government.

PY - 2003/10/13

Y1 - 2003/10/13

N2 - The ionization potential of thymine functionalized at the C5 position with the truncated linker groups, -CH=CHCO2CH3 and -CH=CHCONHCH3, was examined using density functional theory. Results indicate that the addition of the carboxyl group to thymine lowers the adiabatic ionization potential by 0.4 eV. Further, modification of the carboxyl group by an amino group lowers the ionization potential by another 0.2 eV. The effect of solvation and base pairing with adenine on the modified thymine ionization energies was also investigated. The results provide evidence that linker groups can dampen the influence of adenine base pairing on thymine charge transfer.

AB - The ionization potential of thymine functionalized at the C5 position with the truncated linker groups, -CH=CHCO2CH3 and -CH=CHCONHCH3, was examined using density functional theory. Results indicate that the addition of the carboxyl group to thymine lowers the adiabatic ionization potential by 0.4 eV. Further, modification of the carboxyl group by an amino group lowers the ionization potential by another 0.2 eV. The effect of solvation and base pairing with adenine on the modified thymine ionization energies was also investigated. The results provide evidence that linker groups can dampen the influence of adenine base pairing on thymine charge transfer.

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DO - 10.1016/j.cplett.2003.08.072

M3 - Article

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SN - 0009-2614

VL - 380

SP - 54

EP - 62

JO - Chemical Physics Letters

JF - Chemical Physics Letters

IS - 1-2

ER -

Theoretical study of the ionization potential of thymine: Effect of adding conjugated functional groups

Abstract

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