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2 article(s) from Zipse, Hendrik

Azo-dimethylaminopyridine-functionalized Ni(II)-porphyrin as a photoswitchable nucleophilic catalyst

Jannis Ludwig,
Julian Helberg,
Hendrik Zipse and
Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2119–2126, doi:10.3762/bjoc.16.179

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Figure 1: Basicity and nucleophilicity switching of the 4-(N,N-dimethylamino)pyridine “record player” molecul...

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Scheme 1: Synthesis of 4-N,N-dimethylamino record player molecule 1 by Suzuki reaction between Ni-porphyrin p...

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Figure 2: Composition of the different states of porphyrin 1 (1 mM) in the PSS at 530 nm and 435 nm, determin...

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Figure 3: a) UV–vis cuvette with a solution of porphyrin 1 (13.1 µM in THF) and the corresponding UV–vis spec...

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Scheme 2: General scheme of the nitroaldol (Henry) reaction that was used to investigate photoswitchable cata...

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Scheme 3: DMAP (2), azopyridine trans-4, record player trans- and cis-1 and Ni-porphyrin 8 were used in kinet...

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Figure 4: Conversion of 4-nitrobenzaldehyde (6) in the Henry reaction with nitroethane (5) as a function of t...

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Published 31 Aug 2020

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Cation affinity numbers of Lewis bases

Christoph Lindner,
Raman Tandon,
Boris Maryasin,
Evgeny Larionov and
Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

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Scheme 1: Reactions for the methyl cation affinity (MCA) of a neutral Lewis base (1a), an anionic Lewis base ...

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Figure 1: MCA values of monosubstituted amines of general formula Me₂N(CH₂)_nH (n = 1–7, in kJ/mol).

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Scheme 2: Systematic dependence of MCA.

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Scheme 3: Trends in amine MCA values.

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Figure 2: Eclipsing interactions in the best conformation of N⁺Me(iPr)₃ (16Me) (left), and the corresponding ...

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Scheme 4: General expression for the chain-length dependence of MCA values.

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Figure 3: MCA values of monosubstituted phosphanes of general formula Me₂P(CH₂)_nH (n = 1–8, in kJ/mol).

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Figure 4: MCA values of monosubstituted phosphanes of general formula PMe₂(CH(CH₂)_n₊₁) (n = 1–8, in kJ/mol).

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Figure 5: The MCA values of n-butyldiphenylphosphane (102) and its (αα-/ββ-/γγ-) dimethylated analogues.

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Figure 6: MCA values of phosphanes Me₂P–NR₂ with cyclic and acyclic amine substituents.

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Figure 7: MCA values of phosphanes PMe₂R connected to α,α- and β,β-position of nitrogen containing cyclic sub...

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Scheme 5: Reactions for the benzhydryl cation affinity (BHCA) of a Lewis base (5a) and pyridine (5b).

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Figure 8: Comparison of BHCA values (kJ/mol) and nucleophilicity parameters N for sterically unbiased pyridin...

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Scheme 6: Reactions for the trityl cation affinity (THCA) of a Lewis base (6a) and pyridine (6b).

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Figure 9: Comparison of MCA, BHCA, and TCA values of selected Lewis bases.

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Scheme 7: Correlations of BHCA/TCA values with the respective MCA data for sterically unbiased systems (exclu...

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Figure 10: Scheme for the angle d(RXRR) measurements.

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Scheme 8: Reactions for the Mosher's cation affinity (MOSCA) of a Lewis base.

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Scheme 9: Reactions for the acetyl cation affinity (ACA) of a Lewis base (9a) and pyridine (9b).

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Figure 11: Structure of the acetylated pyridine 380 (380Ac).

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Scheme 10: Reaction for the Michael-acceptor affinity (MAA) of a Lewis base.

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Figure 12: Inverted reaction free energies for the addition of N- and P-based Lewis bases to three different M...

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Figure 13: Correlation between MCA values and affinity values towards three different Michael acceptors.

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Scheme 11: (a) General definition for a methyl cation transfer reaction between Lewis bases LB¹ and LB², and (...

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Figure 14: The energetically best conformations of Pn-Bu₃ (120_1, top) and (120_2, bottom).

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Figure 15: Relative order of the conformations 120_1 to 120_7 depending on the level of theory.

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Figure 16: The structure of the energetically best conformations of 120Me.

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