Bis[( l )prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Poddar, Roona; Jain, Arti; Kidwai, Mazaahir

doi:10.1016/j.jare.2016.12.005

Cited by 21 publications

(6 citation statements)

References 124 publications

(127 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“… [54] The bidentate coordination of l ‐Pro to the Zn 2+ ion is unlikely, as it would give a DSC peak at higher temperature, ca. 345 °C, in agreement with a stronger binding effect [55] …”

Section: Resultssupporting

confidence: 66%

“…Similar to the PXRD studies, independent of the handedness of the chiral amino acid, the materials have identical FTIR spectra (Figures S4 and S5). The higher concentration of l ‐ and d ‐Pro in the materials obtained in DMF allows to identify the characteristic vibration modes, including the NH stretching at 3216 cm −1 and the CH 2 vibrations in the range 2800–3200 cm −1 (Figure S5) [55] …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Gheorghe

Strudwick

Dawson

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

The synthesis of chiral metal-organic frameworks (MOFs)i sh ighly relevant for asymmetric heterogenous catalysis, yet very challenging. Chiral MOFsw ith MOF-74 topology were synthesised by using post-synthetic modification with proline. Vibrational circular dichroism studies demonstrate that prolinei st he source of chirality.T he solvents used in the synthesis play ak ey role in tuning the loading of proline and its interaction with the MOF-74 framework. In N,N'-dimethylformamide, proline coordinates monodentate to the Zn 2 + ions withint he MOF-74 framework, whereasi ti s only weakly bound to the frameworkw hen using methanol as solvent. Introducing chirality within the MOF-74f ramework also leads to the formation of defects, with both the organic linkera nd metal ions missing from the framework. The formationo fd efects combined with the coordination of DMF and prolinew ithin the framework leads to ap ore blockinge ffect. This is confirmed by adsorption studies and testingo ft he chiral MOFs in the asymmetric aldol reaction betweenacetone and para-nitrobenzaldehyde.

show abstract

Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Gheorghe

Strudwick

Dawson

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Although the synthesis of [Zn(Pro)2] (4) has been already described in the literature [30], the strategy was different from the one we used. It was performed by reacting zinc acetate with proline in the presence of trimethylamine, using methanol as a solvent.…”

Section: Synthesis and Characterization Of Zn(ii) Complexes 1-6mentioning

confidence: 99%

Zinc(II) Complexes with Amino Acids for Potential Use in Dermatology: Synthesis, Crystal Structures, and Antibacterial Activity

et al. 2020

View full text Add to dashboard Cite

The multifunctional profile of Zn2+ has influenced its great popularity in various pharmaceutical, food, and cosmetic products. Despite the use of different inorganic and organic zinc derivatives, the search for new zinc-containing compounds with a safer skin profile still remains an open issue. The present paper describes the synthesis, structural characterization, and antibacterial activity of zinc(II) complexes with proteinogenic amino acids as potential candidates for dermatological treatments. The obtained complexes are of the general formula [Zn(AA)2], where AA represents an amino acid (L-Glu, Gly, L-His, L-Pro, L-Met, and L-Trp). Their synthesis was designed in such a way that the final bis(aminoacidate) zinc(II) complexes did not contain any counter-ions such as Cl−, NO3−, or SO42− that can cause some skin irritations. The chemical structure and composition of the compounds were identified by 1H NMR spectroscopy and elemental analysis, and four were also characterized by single-crystal X-ray diffraction. The Hirshfeld surface analysis for the Zn2+ metallic center helped to determine its coordination number and geometry for each complex. Finally, the antibacterial properties of the complexes were determined with respect to three Gram-positive strains, viz. Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, and Streptococcus pyogenes ATCC 19615, and two Gram-negative bacteria, viz. Escherichia coli ATCC 25992 and Pseudomonas aeruginosa ATCC 27853, and were compared with the activity of zinc 2-pirrolidone 5-carboxylate (ZnPCA), commonly applied in dermatology. It was found that the Zn(II) complexes with methionine and glycine exhibited a higher antibacterial activity than the tested standard, and the antimicrobial properties of complex with Trp were satisfactory. The results of the antimicrobial activity examination allow us to postulate that the obtained zinc complexes might become new active substances for use in dermatological products.

show abstract

“…In the present scenario, there is an increased demand for development of clean and eco‐friendly protocols for various organic transformations ,. The green chemistry principles have encouraged the use of solid acid catalysts as alternatives for conventional and harsh liquid acids such as nitric acid, hydrochloric acid and sulfuric acid which cannot be used in stoichiometric amounts ,.…”

Section: Introductionmentioning

confidence: 99%

Caffeinium Hydrogen Sulfate: A Green Solid Acid Catalyst for Selective One‐Pot Domino Knoevenagel‐Michael Transformations

et al. 2018

Self Cite

View full text Add to dashboard Cite

A green, water soluble and efficient solid acid catalyst Caffeinium Hydrogen Sulfate (CHS) is prepared by sulfonation of caffeine and characterized by 1H‐NMR, 13C‐NMR, FTIR spectroscopy, elemental and thermal analysis. The catalytic application of the prepared catalyst for the selective one‐pot domino Knoevenagel‐Michael synthesis of bis‐cyclohexenones and 1,8‐dioxooctahydroxanthenes is investigated. This report demonstrate the selectivity of CHS to synthesise bis‐cyclohexenone and xanthenes at different temperature conditions. The proposed methodology put forward various advantages such as cost effectiveness, excellent yields of the targeted products, clean and mild reaction profile, negligible waste generation, eliminate the use of harmful organic solvents and corrosive reagents, reusability of the catalytic system and afford pure products without any extraction and purification steps.

show abstract

Bis[( l )prolinate-N,O]Zn: A water-soluble and recycle catalyst for various organic transformations

Abstract: Graphical abstract

Cited by 21 publications

References 124 publications

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Synthesis of Chiral MOF‐74 Frameworks by Post‐Synthetic Modification by Using an Amino Acid

Zinc(II) Complexes with Amino Acids for Potential Use in Dermatology: Synthesis, Crystal Structures, and Antibacterial Activity

Caffeinium Hydrogen Sulfate: A Green Solid Acid Catalyst for Selective One‐Pot Domino Knoevenagel‐Michael Transformations

Contact Info

Product

Resources

About