Through-space electrostatic field effect on protonation energies OF α,ω-diamino acids

Klára Ösapay, G. Náray-Szabó

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Theoretical gas-phase protonation energies, Ep, of the zwitterionic forms of 2,3-diaminopropionic acid, 2,4-diaminobutyric acid, ornithine and lysine are compared. It is shown that the charged carboxylate or ammonium groups strongly influence the value of Ep even if they are located far from the protonated nitrogen atom. Comparing Ep with the minimum electrostatic potentials, calculated from fully transferable bond fragments, it is demonstrated that the above substituents influence protonation energies by a through-space electrostatic, rather than by a through-bond inductive, mechanism. A simple equation is given to estimate substituent effects. By analyzing pKa values, measured in aqueous solution, the primary importance of hydration is stressed.

Original languageEnglish
Pages (from-to)57-62
Number of pages6
JournalJournal of Molecular Structure
Volume92
Issue numberC
DOIs
Publication statusPublished - 1983

Fingerprint

Protonation
Static Electricity
Electrostatics
Electric fields
electrostatics
acids
Acids
Ornithine
electric fields
lysine
Ammonium Compounds
Hydration
nitrogen atoms
carboxylates
Lysine
hydration
Nitrogen
Gases
fragments
vapor phases

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics
  • Computational Theory and Mathematics

Cite this

Through-space electrostatic field effect on protonation energies OF α,ω-diamino acids. / Ösapay, Klára; Náray-Szabó, G.

In: Journal of Molecular Structure, Vol. 92, No. C, 1983, p. 57-62.

Research output: Contribution to journalArticle

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