A DOSY Spectroscopy Study of Proton Exchange Processes Involving Inner N-H Protons in Natural and Synthetic Porphyrins

Dmitriy V. Belykh^a@ and Alexander L. Stolypko^a,b

^aInstitute of Chemistry, Komi Science Centre, Ural Branch of the Russian Academy of Sciences, 167982 Syktyvkar, Russia

^bSyktyvkar State University, 167000 Syktyvkar, Russia

^@Corresponding author E-mail: belykh-dv@mail.ru

DOI: 10.6060/mhc160534b

Macroheterocycles 2017 10(1) 51-56

DOSY spectroscopy was used to assess the involvement of inner N-H protons of porphyrinic compounds in exchange processes. The assessment was made by comparison of increase of self-diffusion coefficients of N-H and C-H protons. The difference in the measured coefficients can serve as a quantitative measure of hydrogen exchange intensity and thus of N-H acidity. Using DOSY allowed to demonstrate that regardless of the strongly different chemical shifts, the N-H bonds in porphyrins and chlorins have similar acidity and the magnetically non-equivalent inner N-H protons in chlorins have a different degree of involvement in exchange processes..

References:

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A DOSY Spectroscopy Study of Proton Exchange Processes Involving Inner N-H Protons in Natural and Synthetic Porphyrins

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