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- Title
Effect of Amino Acid Fragments in Tetraphenylporphin Derivatives on the pH Range of Porphyrin Dications Dominance.
- Authors
Ivanova, Yu. B.; Khrushkova, Yu. V.; Pukhovskaya, S. G.; Lukanov, M. M.; Syrbu, S. A.
- Abstract
The effect of amino acid fragments in tetraphenylporphin derivatives on the pH range of porphyrin dication dominance was studied. For this purpose, the protonation processes of unsymmetrically substituted derivatives of 5,10,15,20-tetraphenylporphyrin: 5-(4′-aminophenyl)-10,15,20-triphenylporphine, 5-(4′-tyrosinylamidophenyl)-10,15,20-triphenylporphine, and 5-(4′-glycinacylaminophenyl)-10,15,20-triphenylporphine in acetonitrile were considered. It was found that in acidic acetonitrile solutions the pH range of dominating the doubly protonated form depends on the nature of the substituent in the para-position of the phenyl fragment on the periphery of the porphyrin ring: electron-donor substituents expand the pH range of dominating the porphyrin dication, whereas electron-acceptor substituents decrease it. The calculation of the energies of the molecular orbitals of the studied compounds by the DFT method with the B3LYP/cc-pVDZ set showed good agreement between the experiment and the calculations.
- Subjects
PORPHYRINS; MOLECULAR orbitals; SOCIAL dominance; AMINO acids; PROTON transfer reactions; ACETONITRILE
- Publication
Russian Journal of General Chemistry, 2023, Vol 93, Issue 7, p1721
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S1070363223070125