Experimental and computational thermodynamics of pyrene and 1-pyrenecarboxaldehyde and their photophysical properties

Santos, Ana Filipa L.O.M.; Oliveira, Juliana A.S.A.; Monte, Manuel J.S.

doi:10.1016/j.jct.2015.07.008

Cited by 21 publications

(10 citation statements)

References 69 publications

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“…These constants were obtained as the average of six independent experiments, with the quoted uncertainty being the standard deviation of the mean for a level of confidence of 0.95. The performance of the system at the temperature of 411.7 K was checked by measuring the standard molar enthalpy of sublimation, at T = 298.15 K, of pyrene, obtaining a value of Δ cr g H m ° = 99.7 ± 2.0 kJ·mol –1 , which is in excellent agreement with the value reported in the literature . Complementary details are given in the Supporting Information (section S4).…”

Section: Experimental Sectionsupporting

confidence: 79%

“…The performance of the system at the temperature of 411.7 K was checked by measuring the standard molar enthalpy of sublimation, at T = 298.15 K, of pyrene, obtaining a value of Δ cr g H m °= 99.7 ± 2.0 kJ• mol −1 , which is in excellent agreement with the value reported in the literature. 27 Complementary details are given in the Supporting Information (section S4).…”

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confidence: 99%

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Energetic and Structural Properties of Two Phenolic Antioxidants: Tyrosol and Hydroxytyrosol

et al. 2018

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Theoretical and experimental studies on the energetic, structural and some other relevant physicochemical properties of the antioxidant tyrosol (1), hydroxytyrosol (1OH) molecules and the corresponding radicals 1 rad• and 1O rad • are reported in this work. The experimental values of the gas-phase enthalpy of formation, Δ f H m 0 (g), in kJ•mol −1 , of 1 (−302.4 ± 3.4) and 1OH (−486.3 ± 4.1) have been determined. Quantum chemical calculations, at DFT (M05-2X) and composite ab initio G3 and G4 levels of theory, provided results that served to (i) confirm the excellent consistency of the experimental measurements performed, (ii) establish that the stabilizing effect of H-bond of hydroxyethyl chain and aromatic ring (OH•••π interaction) is smaller in radicals than in parent molecules, (iii) deducecombining experimental data in isodesmic reactionsΔ f H m 0 (g) of radicals 1 rad • (−152.3 ± 4.4 kJ• mol −1 ) and 1O rad • (−370.6 ± 3.8 kJ•mol −1 ), (iv) estimate a reliable O−H bond dissociation enthalpy, BDE of 1 (368.1 ± 5.6 kJ•mol −1 ) and of 1OH (333.7 ± 5.6 kJ• mol −1 ), and (v) corroborateusing "BDE criteria"than 1OH is a more effective antioxidant than 1.

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Section: Experimental Sectionsupporting

confidence: 79%

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confidence: 99%

Energetic and Structural Properties of Two Phenolic Antioxidants: Tyrosol and Hydroxytyrosol

et al. 2018

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“…Thus, recalculation of p 0,cr to p 0,l is increasingly uncertain with the length of extrapolation below T fus . Recalculation according to eqs and was concisely described by Allen et al, though numerical values of this work would deserve amendment since new sublimation pressures for most PAHs treated in this paper were published afterward. − Examples of eq utilization are also given in van Noort, Růžička et al, and Mahnel et al for anthracene, which is relevant to this section.…”

Section: Evaluation Of Literature Cgc Vapor Pressuresmentioning

confidence: 95%

Estimating Vapor Pressure Data from Gas–Liquid Chromatography Retention Times: Analysis of Multiple Reference Approaches, Review of Prior Applications, and Outlook

et al. 2022

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Reliable methods for determining the vapor pressures of organic materials are of increasing importance as a tool for predicting the behavior and fate of chemicals that are introduced into the environment. In the present work, we analyze the method that relates the gas–liquid chromatography (GLC) retention data, namely, the retention factors (k) of selected organic compounds with their vapor pressures (p 0) using multiple reference standards. Temperature-dependent k values of test chemicals and an adequate number y of reference standard chemicals having directly measured vapor pressure values at temperatures corresponding to GLC measurements are required to apply this method (GLC-RTyS). Retention data of 49 test compounds including a series of alkanes, alkanols, alkyl benzenes, phenols, some (hydro)naphthalene derivatives, and menthol determined on a low-polar dimethylpolysiloxane (HP-1) column at a temperature range from 353 K to (403 or 423) K were used for method validation. We present a first systematic analysis aimed at examining whether and to what extent the selection of experimental conditions might influence/improve the results. Furthermore, we present a review of an alternative multireference correlation gas chromatographic (CGC) method that employs significant extrapolations and is based on the use of adjusted retention time t′ instead of k in order to reveal uncertainties inherent in routine application of this method.

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“…An especially extended amount of research has been done with hydrocarbons including alkanes, alkenes, alkynes, and aromatics , forming the core of the various carbon groups. In addition, many data have dealt specifically with alcohols and phenol derivatives [61][62][63][64][65][66][67][68][69][70][71][72][73][74], ethers [75][76][77][78][79][80][81][82][83][84], carbaldehydes [85][86][87][88][89][90][91][92][93][94], ketones [95][96][97][98][99][100][101][102][103][104][105][106][107][108][109]...…”

Section: Sources Of Heat-of-combustion and Formation Datamentioning

confidence: 99%

Revision and Extension of a Generally Applicable Group-Additivity Method for the Calculation of the Standard Heat of Combustion and Formation of Organic Molecules

Naef

Acree

2021

Molecules

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The calculation of the heats of combustion DH°c and formation DH°f of organic molecules at standard conditions is presented using a commonly applicable computer algorithm based on the group-additivity method. This work is a continuation and extension of an earlier publication. The method rests on the complete breakdown of the molecules into their constituting atoms, these being further characterized by their immediate neighbor atoms. The group contributions are calculated by means of a fast Gauss–Seidel fitting calculus using the experimental data of 5030 molecules from literature. The applicability of this method has been tested by a subsequent ten-fold cross-validation procedure, which confirmed the extraordinary accuracy of the prediction of DH°c with a correlation coefficient R2 and a cross-validated correlation coefficient Q2 of 1, a standard deviation σ of 18.12 kJ/mol, a cross-validated standard deviation S of 19.16 kJ/mol, and a mean absolute deviation of 0.4%. The heat of formation DH°f has been calculated from DH°c using the standard enthalpies of combustion for the elements, yielding a correlation coefficient R2 for DH°f of 0.9979 and a corresponding standard deviation σ of 18.14 kJ/mol.

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Experimental and computational thermodynamics of pyrene and 1-pyrenecarboxaldehyde and their photophysical properties

Cited by 21 publications

References 69 publications

Energetic and Structural Properties of Two Phenolic Antioxidants: Tyrosol and Hydroxytyrosol

Energetic and Structural Properties of Two Phenolic Antioxidants: Tyrosol and Hydroxytyrosol

Estimating Vapor Pressure Data from Gas–Liquid Chromatography Retention Times: Analysis of Multiple Reference Approaches, Review of Prior Applications, and Outlook

Revision and Extension of a Generally Applicable Group-Additivity Method for the Calculation of the Standard Heat of Combustion and Formation of Organic Molecules

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