How acidic are corroles and why?

Mahammed, Atif; Weaver, Jeremy J.; Gray, Harry B.; Abdelas, Meirav; Gross, Zeev

doi:10.1016/s0040-4039(03)00174-6

Cited by 75 publications

(88 citation statements)

References 12 publications

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“…We were not able to record interpretable spectra for either of these two macrocycles under ESI(Ϫ) conditions. This result is surprising for TPC as its acidity is reportedly much higher than that of porphyrins [39].…”

Section: Esi(ϩ) Ms and Ms/ms Of Tpp And Tpcmentioning

confidence: 92%

Observation of phenyl-fused porphyrinoids during the ESI mass spectrometric analysis of meso-pentafluorophenyl-substituted porphyrin and corrole

Lau

Sadı́lek

Gouterman

et al. 2006

J. Am. Soc. Mass Spectrom.

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The results of ESI(ϩ) and ESI(Ϫ) mass spectrometry/mass spectrometry investigations of meso-tetrakisphenylporphyrin (TPP) and meso-trisphenylcorrole (TPC) in comparison with their meso-tetrakis(pentafluorophenyl)-substituted analogs T F PP and T F PC are reported. The fragmentation patterns of TPP and TPC show the expected loss of meso-aryl radicals. Analyzing the meso-pentafluorophenyl substituted analogs T F PP and T F PC, we found ESI(Ϫ) to be an excellent ionization mode. Rich and well-defined HF-elimination fragmentation patterns unique to the presence of meso-tetrafluorophenyl groups and evocative for the formation of fragments with direct covalent o-phenyl-to-␤-linkages are observed. A computation of the feasibility and relative energies of the resulting species corroborates the interpretation of the experimental findings. The computations indicate the presence of cooperative interactions between the linkages that direct the linkage formations to occur in a unidirectional fashion. MS/MS/MS experiments also provide indications for the regioselectivity of the fusions. Our observations further detail earlier reports of similar HF-eliminations and allow a generalization of the findings. The results presented may also point to strategies towards the bulk synthesis of novel porphyrinoid structures. (J Am Soc Mass Spectrom 2006, 17, 1306 -1314

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Section: Esi(ϩ) Ms and Ms/ms Of Tpp And Tpcmentioning

confidence: 92%

Observation of phenyl-fused porphyrinoids during the ESI mass spectrometric analysis of meso-pentafluorophenyl-substituted porphyrin and corrole

Lau

Sadı́lek

Gouterman

et al. 2006

J. Am. Soc. Mass Spectrom.

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“…This origin of fluorescence reduction upon the addition of transferrin is most likely quite different for the metal-free and the gallium corrole, but the current observations may be rationalized by previous findings. The major factor affecting fluorescence intensity of 1 is the number of NH protons in its inner core, with the deprotonated corrole (2 NH's) being more fluorescent than the neutral (3 NH's) and much more than the protonated (4 NH's) corrole [24]. Since the deprotonated corrole is dominant at pH 7.4, the reduction in fluorescence intensity observed by treating aqueous solutions of 1 with transferrin apparently reflect a smaller degree of corrole deprotonation in the hydrophobic pocket.…”

Section: Emission Spectramentioning

confidence: 99%

Corroles that bind with high affinity to both apo and holo transferrin

Haber

Agadjanian

Medina-Kauwe

et al. 2008

Journal of Inorganic Biochemistry

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“…(ii) Imine nitrogen atoms from the corrole cavity can be protonated at low pH. Actually, corroles are monoprotonated by relatively weak acids, and the second protonation most probably occurs on C-5 [22][23][24]. This is not expected in the case of calix [4]pyrrole.…”

Section: Introductionmentioning

confidence: 99%

Nitrogen-Containing Macrocycles as Host Molecules for the Recognition of Undissociated Phenol Derivatives: Mechanism of Potentiometric Signal Generation

Radecki

Dehaen²

2006

CCHTS

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The mechanism of the generation of potentiometric signals of corrole- and calix[4]pyrrole-containing liquid membrane electrodes was elucidated and compared in the presence of the neutral forms of phenol derivatives. In addition, the influence of lipophilic, anionic or cationic salts on this phenomenon was explored. Finally, the relationship between the acid-base properties of the phenolic guests and the hydrogen bond donor activity of the calix[4]pyrrole and corrole hosts, and the influence on the molecular recognition phenomenon occurring at the organic/aqueous interface are discussed.

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How acidic are corroles and why?

Cited by 75 publications

References 12 publications

Observation of phenyl-fused porphyrinoids during the ESI mass spectrometric analysis of meso-pentafluorophenyl-substituted porphyrin and corrole

Observation of phenyl-fused porphyrinoids during the ESI mass spectrometric analysis of meso-pentafluorophenyl-substituted porphyrin and corrole

Corroles that bind with high affinity to both apo and holo transferrin

Nitrogen-Containing Macrocycles as Host Molecules for the Recognition of Undissociated Phenol Derivatives: Mechanism of Potentiometric Signal Generation

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