Bulletin of the Korean Chemical Society

  • 제33권5호
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  • Pages.1561-1565
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  • 2012
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Structure and Intramolecular Proton Transfer of Alanine Radical Cations

  • Lee, Gab-Yong (Department of Life Chemistry, Catholic University of Daegu)
  • 투고 : 2011.12.22
  • 심사 : 2012.02.04
  • 발행 : 2012.05.20
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초록

The structures of the four lowest alanine conformers, along with their radical cations and the effect of ionization on the intramolecular proton transfer process, are studied using the density functional theory and MP2 method. The energy order of the radical cations of alanine differs from that of the corresponding neutral conformers due to changes in the basicity of the $NH_2$ group upon ionization. Ionization favors the intramolecular proton transfer process, leading to a proton-transferred radical-cation structure, [$NH_3{^+}-CHCH_3-COO{\bullet}$], which contrasts with the fact that a proton-transferred zwitterionic conformer is not stable for a neutral alanine in the gas phase. The energy barrier during the proton transfer process is calculated to be about 6 kcal/mol.

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피인용 문헌

  1. DFT Study of the Effects of Halogen Anions on the Stability of Alanine Zwitterion vol.35, pp.4, 2014, https://doi.org/10.5012/bkcs.2014.35.4.1202
  2. A DFT Study of the Intramolecular Hydrogen Bonding of Alanine and Its Effects on Ionization Energies vol.59, pp.6, 2015, https://doi.org/10.5012/jkcs.2015.59.6.541
  3. A theoretical and experimental 1H NMR spectroscopy study of the stereoelectronic interactions that rule the conformational energies of alanine and valine methyl ester vol.26, pp.10, 2013, https://doi.org/10.1002/poc.3180
  4. Reactions between neutral molecules and cation-radicals in the gas-phase: Can protonation occur without proton transfer? vol.390, pp.None, 2015, https://doi.org/10.1016/j.ijms.2015.08.019