Proton Exchange of Intracyclic NH Groups of Deuteroporphyrin IX Dimethyl Ester and Water Molecules according to the Data of Exchange Spectroscopy (EXSY)

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

^aSyktyvkar State University, 167000 Syktyvkar, Russia

^bInstitute of Сhemistry of Komi Scientific Centre of the Ural Branch of the Russian Academy of Sciences, 167982 Syktyvkar, Russia

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

DOI: 10.6060/mhc210129b

Macroheterocycles 2021 14(2) 147-152

In this work, the EХSY method was used to measure the proton exchange rate constant with the participation of water molecules and intracyclic NH groups of dimethyl ester of deuteroporphyrin IX, taking into account the contribution of cross-relaxation. Comparison with the similar measurements by the DOSY method makes it possible to construct a more complete picture of exchange processes for dimethyl ester of deuteroporphyrin IX, to point out the main limiting stages, and determine the corresponding rate constants.

References:

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1. Thomas K.E., McCormick L.J., Vazquez-Lima H., Ghosh A. Angew. Chem. Int. Ed. 2017, 56, 10088-10092.
https://doi.org/10.1002/anie.201701965

2. Udal'tsov A.V., Kazarin L.A., Sinani V.A., Sweshnikov A.A. J. Photochem. Photobiol. A: Chem. 2002, 151, 105-119.
https://doi.org/10.1016/S1010-6030(02)00145-4

3. Udal'tsov A.V., Bolshakova A.V., Vos J.G. J. Mol. Struct. 2014, 1065-1066, 170-178.
https://doi.org/10.1016/j.molstruc.2014.02.055

4. Yang J., Wang Z., Hu K., Li Y., Feng J., Shi J., Gu J. ACS Appl. Mater. Interfaces 2015, 7, 11956-11964.
https://doi.org/10.1021/acsami.5b01946

5. Kielmann M., Senge M.O. Angew. Chem. Int. Ed. 2019, 58, 418 - 441.
https://doi.org/10.1002/anie.201806281

6. Hikal W.M., Harmon H.J. J. Hazardous Mater. 2008, 154, 826-831.
https://doi.org/10.1016/j.jhazmat.2007.10.098

7. Stolypko A.L., Belykh D.V. Macroheterocycles 2018, 11, 383-389.
https://doi.org/10.6060/mhc180689b

8. Belykh D.V., Stolypko A.L. Macroheterocycles 2019, 12, 392-397.
https://doi.org/10.6060/mhc190444b

9. Gragerov I.P., Pogorely V.K., Franchuk I.F. Hydrogen Bond and Fast Proton Exchange. Kiev: Nauk. Dumka, 1978. 215 p.

10. Stolypko A.L., Belykh D.V. Macroheterocycles 2019, 12, 398-402.
https://doi.org/10.6060/mhc191280b

11. Ernst R., Bodenhausen G., Wokaun A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions. ISBN 5-03-001394-6 (transl. into Russ., Moscow: Mir, 1990, 711 p.).

12. Hasani M., Nordstierna L., Martinelli A. Phys. Chem. Chem. Phys. 2019, 21, 22014-22021.
https://doi.org/10.1039/C9CP03563J

13. Dimitrov V.S., Vassilev N. G. Magnetic Resonance in Chemistry 1995, 33, 739-744.
https://doi.org/10.1002/mrc.1260330909

14. Krishnan V. V. Inventions 2019, 4, 13;
https://doi.org/10.3390/inventions4010013

15. Green A.R., Li K., Lockard B., Young R.P., Mueller L.J., Larive C.K. J Phys Chem B. 2019, 123(22), 4653-4662.
https://doi.org/10.1021/acs.jpcb.9b01794

16. Swartjes A., White P.B., Lammertink M., Elemans J.A.A.W., Nolte R.J.M. Angew. Chem. 2020, 132, 2-11.
https://doi.org/10.1002/anie.202010335

17. Yatsunyk L.A., Ogura H., Ann Walker F. Inorg. Chem. 2005, 44, 2867-2881.
https://doi.org/10.1021/ic049090p

18. Ghini V., Chevance S., Turano P. J. Inorg. Biochem. 2019, 192, 25-32.
https://doi.org/10.1016/j.jinorgbio.2018.12.006

19. Zimmerman D., Goto J.J., Krishnan V.V. PLoS ONE 11(8): e0160491.
https://doi.org/10.1371/journal.pone.0160491

20. Zhang T., Mao X.-A. Applied Magnetic Resonance 2001, 20(1-2), 189-202.
https://doi.org/10.1007/BF03162319

21. Porphyrins: Structure, Properties, Synthesis (Enikolopyan N.S., Ed.), Moscow: Nauka, 1985. 334 p.

22. Jeener J., Meier B. H., Bachmann P., Ernst R. R. J. Chem. Phys. 1979, 71, 4546-4553.
https://doi.org/10.1063/1.438208

23. Bento E.S., Bradley D.C., Hawkes G.E., Maia I.A., Sales K.D. Magn. Reson. Chem. 2000, 38, 331-335.
https://doi.org/10.1002/1097-458X(200005)38:5<331::AID-MRC648>3.0.CO;2-3

24. Slipchenko L.V., Gordon M.S. J. Phys. Chem. A 2009, 113, 2092-2102.
https://doi.org/10.1021/jp808845b

25. Oka K., Shibue T., Sugimura N., Watabe Y., Winther-Jensen B., Nishide H. Sci. Rep. 2019, 9, 223.
https://doi.org/10.1038/s41598-018-36787-1

26. Tachikawa H., Iura R., Kawabata H. Sci. Rep. 2019, 9, 2377.
https://doi.org/10.1038/s41598-019-39319-7

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Proton Exchange of Intracyclic NH Groups of Deuteroporphyrin IX Dimethyl Ester and Water Molecules according to the Data of Exchange Spectroscopy (EXSY)

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