Gas‐phase basicity of 2‐furaldehyde

Ricci, A.; Piccolella, Simona; Pepi, Federico; Patsilinakos, Alexandros; Ragno, Rino; Garzoli, Stefania; Giacomello, Pierluigi

doi:10.1002/jms.3058

Cited by 6 publications

(3 citation statements)

References 42 publications

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“…During the last 30 years, the method has been revised and improved by the contribution of many groups including Fenselau, , Wesdemiotis, − Armentrout, − and Ervin . As a result, the KM has become one of the most frequently used experimental approaches for measuring thermochemical parameters by mass spectrometry, − and its use has been expanded to include the study of enantiomeric analysis of optically active compounds. , …”

Section: Introductionmentioning

confidence: 99%

Gas Phase Acidity Measurement of Local Acidic Groups in Multifunctional Species: Controlling the Binding Sites in Hydroxycinnamic Acids

et al. 2013

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The applicability of the extended kinetic method (EKM) to determine the gas phase acidities (GA) of different deprotonable groups within the same molecule was tested by measuring the acidities of cinnamic, coumaric, and caffeic acids. These molecules differ not only in the number of acidic groups but in their nature, intramolecular distances, and calculated GAs. In order to determine independently the GA of groups within the same molecule using the EKM, it is necessary to selectively prepare pure forms of the hydrogen-bound heterodimer. In this work, the selectivity was achieved by the use of solvents of different vapor pressure (water and acetonitrile), as well as by variation of the drying temperature in the ESI source, which affected the production of heterodimers with different solvation energies and gas-phase dissociation energies. A particularly surprising finding is that the calculated solvation enthalpies of water and the aprotic acetonitrile are essentially identical, and that the different gas-phase products generated are apparently the result of their different vapor pressures, which affects the drying mechanism. This approach for the selective preparation of heterodimers, which is based on the energetics, appears to be quite general and should prove useful for other studies that require the selective production of heterodimers in ESI sources. The experimental results were supported by density functional theory (DFT) calculations of both gas-phase and solvated species. The experimental thermochemical parameters (deprotonation ΔG, ΔH, and ΔS) are in good agreement with the calculated values for the monofunctional cinnamic acid, as well as the multifunctional coumaric and caffeic acids. The measured GA for cinnamic acid is 334.5 ± 2.0 kcal/mol. The measured acidities for the COOH and OH groups of coumaric and caffeic acids are 332.7 ± 2.0, 318.7 ± 2.1, 332.2 ± 2.0, and 317.3 ± 2.2 kcal/mol, respectively.

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Section: Introductionmentioning

confidence: 99%

Gas Phase Acidity Measurement of Local Acidic Groups in Multifunctional Species: Controlling the Binding Sites in Hydroxycinnamic Acids

et al. 2013

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“…Furfural is a chemical used for the synthesis of fine chemicals manufacture 84 . It is also commonly used as sustainable intermediate for the preparation of a great variety of chemicals, pharmaceuticals and furan-based polymers 85 , and, 4. Cyclotene only appeared in WVEuc and is reportedly used as anti-inflammatory agent 86,87 .…”

Section: Carbonyl Groupsmentioning

confidence: 99%

Elucidating the Chemical Properties and Potential Applications of Wood vinegars Produced by Controlled Thermal Treatments

Morales¹,

Marcílio²,

Silva³

et al. 2019

IJAERS

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Wood vinegar (WV) has been used for ages as fertilizer and antimicrobial agent, but its impacts on ecosystems are not well understood. Our objective was to investigate potential uses for WVs made from biomass resources and evaluate conditions for possible agronomic, chemical/pharmaco-chemical purposes and potential impact on the environment. We studied four woods vinegars made by slow pyrolysis using: Cambara (WVCam), Eucaliptus (WVEuc) at 350ºC for 72 h, Nim (WVNim) and Nim mixed with fresh Nim leaves and branches, soaked into WVNim (WVMix) at 120ºC for 40 h. WVs from WVMix, WVEuc and WVCam demonstrated significant potential chemical products, while WVNim for pharmaceutical purposes. WVs can be used to partially substitute fertilizers and chemicals, most especially WVMix. Soil bacteria tests suggest a concentration of 0.8% or less for WVs application in soils. No WVs tested presented risk for environmental and human health due to absence of carcinogenic poly-aromatic hydrocarbons (PAHs).

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“…22 For example, Ricci et al applied the modified form of the extended kinetic method for the GB measurement of 2-furaldehyde. 23 In brief, the method applied for the PA/GB measurements in the present study is achieved by measuring the ln (AH þ /BH þ ), (where A is the analyte in the present study, a particular drug, and B is the reference compound) at a series of low collision energies (CEs) for a set of reference compounds.…”

Section: Introductionmentioning

confidence: 99%

Gas-phase basicity and proton affinity measurements of Alzheimer's disease drugs by the extended kinetic method and a theoretical investigation

Nagaveni

Karthikraj

Chitumalla

et al. 2020

Eur J Mass Spectrom (Chichester)

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This study has been carried out to obtain the thermochemical parameters of drugs used for Alzheimer’s disease. The measurement of gas-phase basicity (GB) and proton affinity (PA) values of four important and commercially available drugs for Alzheimer's disease namely, rivastigmine, galantamine, memantine, and tacrine, is attempted for the first time. This study also includes the measurement of GB and PA values for the proposed drug curcumin, a natural product. We calculated the GB and PA values for all these drugs by applying electrospray ionization tandem mass spectrometry (ESI-MS/MS) with the extended kinetic method. Since, all these drugs possessing amino groups (basic nature), the PA values for all these drugs are high i.e., the PA values range from 923.6 to 979.7 kJ/mol and the GB values range from 886.2 to 943.3 kJ/mol. The GB and PA values obtained from the mass spectrometric experiments are well supported with the theoretical calculations. A high-level theoretical B3LYP/6-311 + G(d,p) method is used for the PA and GB calculation and the deviations are in the acceptable range.

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Gas‐phase basicity of 2‐furaldehyde

Cited by 6 publications

References 42 publications

Gas Phase Acidity Measurement of Local Acidic Groups in Multifunctional Species: Controlling the Binding Sites in Hydroxycinnamic Acids

Gas Phase Acidity Measurement of Local Acidic Groups in Multifunctional Species: Controlling the Binding Sites in Hydroxycinnamic Acids

Elucidating the Chemical Properties and Potential Applications of Wood vinegars Produced by Controlled Thermal Treatments

Gas-phase basicity and proton affinity measurements of Alzheimer's disease drugs by the extended kinetic method and a theoretical investigation

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