Reactivity of octa(2,6-fluorophenyl)porphyrazine in acid-base interaction with nitrogen organic bases

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Abstract

An interaction between octa(2,6-fluorophenyl)porphyrazine and pyridine, 2-methylpyridine, morpholine, piperidine, n-buthylamine, tert-buthylamine, diethylamine and triethylamine in benzene medium. Acid-base reaction between macroheterocycle and piperidine or n-buthylamine is a slow process resulting in forming the kinetically stable complexes with the proton transfer. The structures of these complexes are optimized using CAM-B3LYP/cc-pVTZ method. The changes in reactivity of octa(2,6-fluorophenyl)porphyrazine are analyzed as a function of spatial structure and proton-accepting ability of nitrogen base.

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O. A. Petrov

Ivanovo State University of Chemistry and Technology

Author for correspondence.
Email: poa@isuct.ru
ORCID iD: 0000-0003-3424-7135
Russian Federation, prosp. Sheremetevskii, 7, Ivanovo, 153000

G. A. Gamov

Ivanovo State University of Chemistry and Technology

Email: poa@isuct.ru
ORCID iD: 0000-0002-5240-212X
Russian Federation, prosp. Sheremetevskii, 7, Ivanovo, 153000

N. V. Chizhova

Krestov Institute of Solution Chemistry of Russian Academy of Sciences

Email: poa@isuct.ru
ORCID iD: 0000-0001-5387-5933
Russian Federation, ul. Akademicheskaya, 1, Ivanovo, 153045

N. Z. Mamardashvili

Krestov Institute of Solution Chemistry of Russian Academy of Sciences

Email: poa@isuct.ru
Russian Federation, ul. Akademicheskaya, 1, Ivanovo, 153045

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Supplementary files

Supplementary Files
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2. Fig. 1. EAS of H2Pa(C6H3F2)8 in benzene (1) and piperidine (2) at 298 K

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3. Fig. 2. Change in the ESP of H2Pa(C6H3F2)8 in the presence of piperidine for 54 min at 323 K and СоPip= 2.53 mol/l in benzene

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4. Fig. 3. Change in the ESP of H2Pa(C6H3F2)8 in the presence of n-butylamine for 68 min at 323 K and СоBuNH2= 2.53 mol/l in benzene

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5. Fig. 4. Dependence of lgCo/C on the reaction time of H2Pa(C6H3F2)8 with piperidine (1), n-butylamine (2) in benzene at 343K and СоPip = СоBuNH2= 3.80 mol/l

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6. Fig. 5. Dependence of lgkH343 on lgCoB for the reaction of H2Pa(C6H3F2)8 with piperidine (1) and n-butylamine (2) at 343K

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7. Fig. 6. Structures of H2Pa(C6H3F2)8 (a) and [HPa(C6H3F2)8 HB] with piperidine (b) and n-butylamine (c) optimized by the CAM-B3LYP method

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8. Fig. 7. The structure of [Pa(C6H3F2)8]··· [HB]2 with piperidine (a) and n-butylamine (b) optimized by the CAM-B3LYP method

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9. Scheme

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