Quantum-chemical study on the successive protonation of pyrazine

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Abstract

The protonation of pyrazine is investigated by geometry optimization. Ab initio calculations were carried out for the neutral pyrazine molecule, the pyrazine monocation and the pyrazine bication, using the Gaussian 80 program with a minimal (STO-3G) basis set. Similar calculations were also performed with the CNDO/force method. The results for pyrazine show that in some cases CNDO results are nearer to the experimental data than the ab initio ones. According to the ab initio calculations both CH and NH bonds are lengthened by the proton gains. The NC bond lengthens stepwise, but the CC bond only lengthens at the second protonation. The CNC and NCH angles increase and the NCC and CNH angles decrease upon protonation. The Mulliken population analysis shows that the ring bond lengths depend on the 2pπ - 2pπ overlap densities, the CNC angles on the 2(px + py)/2s population ratio on the nitrogen, while the NCC angles depend on the π charges on the carbon atom.

Original languageEnglish
Pages (from-to)289-295
Number of pages7
JournalJournal of Molecular Structure: THEOCHEM
Volume149
Issue number3-4
DOIs
Publication statusPublished - 1987

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Pyrazines
pyrazines
Protonation
Bond length
Protons
Nitrogen
Atoms
Molecules
Carbon
Geometry
Population
methylidyne
nitrogen
optimization
protons
carbon
rings
geometry
atoms
molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Quantum-chemical study on the successive protonation of pyrazine. / Billes, F.

In: Journal of Molecular Structure: THEOCHEM, Vol. 149, No. 3-4, 1987, p. 289-295.

Research output: Contribution to journalArticle

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