Theoretical study of the hydrogen bonding ability of phenol and its ortho, meta and para substituted derivatives

Remko, Milan; Polčin, J.

doi:10.1016/0378-4487(77)80037-x

Cited by 11 publications

(5 citation statements)

References 12 publications

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“…3). The more positive the partial charge of the phenolic carbon the stronger the H-bond formed (Remko and Polcin, 1977). In the work by Remko and Polcin (Remko and Polcin, 1977) is supported by the experimental work by Stymne et al (Stymne et al, 1973) which also showed the meta substituted derivative having a higher H-bond energy relative to the unsubstituted phenol and the para isomer having a lower H-bond energy.…”

Section: Solid State Vapour Pressurementioning

confidence: 74%

“…In the work by Remko and Polcin (Remko and Polcin, 1977) is supported by the experimental work by Stymne et al (Stymne et al, 1973) which also showed the meta substituted derivative having a higher H-bond energy relative to the unsubstituted phenol and the para isomer having a lower H-bond energy. The work by Remko and Polcin (Remko and Polcin, 1977) investigated the H-bonding potential to formamide and the work by Stymne et al (Stymne et al, 1973) investigated the H-bonding potential to dimethylacetamide. The H-bond energies and the partial charge of the phenolic OH are shown in Table 4 and the chemical structures of the methoxyphenols are shown in Fig.…”

Section: Solid State Vapour Pressurementioning

confidence: 81%

“…There is a slight discrepancy between 2-methoxyphenol and the 4-methoxyphenol where 2-methoxyphenol has a higher H-bond energy, but a lower partial charge of the phenolic carbon than 4methoxyphenol. This is likely due to 2-methoxyphenol being capable of forming an intramolecular H-bond, which whilst being weak and the intermolecular H-bond dominating (Remko and Polcin, 1977), will still impact the calculated partial charge.…”

Section: Solid State Vapour Pressurementioning

confidence: 99%

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Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Shelley¹,

Bannan²,

Worrall³

et al. 2020

Preprint

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Abstract. Knudsen Effusion Mass Spectrometry (KEMS) was used to measure the solid state saturation vapour pressure (PSsat) of a range of atmospherically relevant nitroaromatic compounds over the temperature range from 298 to 328 K. The selection of species analysed contained a range of geometric isomers and differing functionalities, allowing for the impacts of these factors on saturation vapour pressure (Psat) to be probed. Three subsets of nitroaromatics were investigated, nitrophenols, nitrobenzaldehydes and nitrobenzoic acids. The PSsat were converted to sub-cooled liquid saturation vapour pressures (PLsat) using experimental enthalpy of fusion and melting point values measured using differential scanning calorimetry (DSC). The PLsat were compared to those estimated by predictive techniques and, with a few exceptions, were found to be up to 7 orders of magnitude lower. The large differences between the estimated PLsat and the experimental can be attributed to the predictive techniques not containing parameters to adequately account for functional group positioning around an aromatic ring, or the interactions between said groups. When comparing the experimental PSsat of the measured compounds the ability to hydrogen bond (H-Bond), and the strength of a H-bond formed appear to have the strongest influence on the magnitude of the Psat with steric effects and molecular weight also being major factors. Comparisons were made between the KEMS system and data from diffusion-controlled evaporation rates of single particles in an electrodynamic balance (EDB). The KEMS and the EDB showed good agreement with each other for the compounds investigated.

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Section: Solid State Vapour Pressurementioning

confidence: 74%

Section: Solid State Vapour Pressurementioning

confidence: 81%

Section: Solid State Vapour Pressurementioning

confidence: 99%

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Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Shelley¹,

Bannan²,

Worrall³

et al. 2020

Preprint

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“…If intramolecular H-bonding dominates, then very little intermolecular H-bonding can occur, leading to an increase in P sat L . Whilst it is possible for vanillin and isovanillin to form internal H-bonds between the phenol and methoxy groups, it has been shown both theoretically [44] and experimentally [45] that these intramolecular H bonds are weak and the H-bonding is dominated by intermolecular H-bonding. re ± 75%.…”

Section: H-bonding Compoundsmentioning

confidence: 99%

“…If intramolecular H-bonding dominates, then very little intermolecular H-bonding can occur, leading to an increase in . Whilst it is possible for vanillin and isovanillin to form internal H-bonds between the phenol and methoxy groups, it has been shown both theoretically [44] and experimentally [45] that these intramolecular H bonds are weak and the H-bonding is dominated by intermolecular H-bonding. 4-hydroxybenzaldehyde can be directly compared to 3-hydroxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde and vanillin, with 4-hydroxybenzaldehyde having a lower and larger partial charge of the phenolic carbon than each of these compounds, matching the expected trend as can be seen in Figure 2.…”

Section: H-bonding Compoundsmentioning

confidence: 99%

Measured Solid State and Sub-Cooled Liquid Vapour Pressures of Benzaldehydes Using Knudsen Effusion Mass Spectrometry

et al. 2021

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Benzaldehydes are components of atmospheric aerosol that are poorly represented in current vapour pressure predictive techniques. In this study the solid state (PSsat) and sub-cooled liquid saturation vapour pressures (PLsat) were measured over a range of temperatures (298–328 K) for a chemically diverse group of benzaldehydes. The selected benzaldehydes allowed for the effects of varied geometric isomers and functionalities on saturation vapour pressure (Psat) to be probed. PSsat was measured using Knudsen effusion mass spectrometry (KEMS) and PLsat was obtained via a sub-cooled correction utilising experimental enthalpy of fusion and melting point values measured using differential scanning calorimetry (DSC). The strength of the hydrogen bond (H-bond) was the most important factor for determining PLsat when a H-bond was present and the polarisability of the compound was the most important factor when a H-bond was not present. Typically compounds capable of hydrogen bonding had PLsat 1 to 2 orders of magnitude lower than those that could not H-bond. The PLsat were compared to estimated values using three different predictive techniques (Nannoolal et al. vapour pressure method, Myrdal and Yalkowsky method, and SIMPOL). The Nannoolal et al. vapour pressure method and the Myrdal and Yalkowsky method require the use of a boiling point method to predict Psat. For the compounds in this study the Nannoolal et al. boiling point method showed the best performance. All three predictive techniques showed less than an order of magnitude error in PLsat on average, however more significant errors were within these methods. Such errors will have important implications for studies trying to ascertain the role of these compounds on aerosol growth and human health impacts. SIMPOL predicted PLsat the closest to the experimentally determined values.

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Molecular calculations with the nonempirical ab initioMODPOT, VRDDO, and MODPOT/VRDDO procedures. XI. Theoretical study of the [C₆H₅OH ⃛OC₆H₅]⁻ molecular complex: Ab initioMODPOT/VRDDO calculations and electrostatic molecular potential contour maps

Sokalski

Hariharan

Popkie

et al. 1980

Int J of Quantum Chemistry

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Thc transport of C h H~O -(or similarly charged moieties) through a lipoidal membrane ma) possibly be facilitated by forming complexes with the neutral compound. Thus, thcorctical studies wcrs perfortiled on the model [C~H5OH--OC~t35]molecular complex to obtain some information conccrning the possible molecular and electronic structure or such complexes. Ah inirio V O D -POT !vKi)I>o SC'F calculations were carried out on the neutral-anion dinier [ChHcOH--OChH<] to uptimi/c thc equilibrium geometry. Electrostatic niolecular potential contour maps have been gcncrated from the ah inirio MODPOT/VKDDO results in the molecular plane and in the plane pcrpcndicular to the inolecular plane and interaccting the hydrogen bond O-.H--O. Difference inaps have also been generated showing the change of potential on complex formation. There is a decrcaac of electrostatic interactions of the phcnoxide anion upon complex formation with the neutral phcnol. Countcrpoiae corrections for basis set s i x could not be made since calculation of the phcnoxide anions in the b et of the phenol plus the phcnoxide anion led to an excited state for thc phenoxide anion. This behavior i\ somewhat similar to that occurring in the stabiliration method for excited states of ncgativc ions as the si7e of thc basis set is increased.

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Theoretical study of the hydrogen bonding ability of phenol and its ortho, meta and para substituted derivatives

Cited by 11 publications

References 12 publications

Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Measured Solid State and Sub-Cooled Liquid Vapour Pressures of Benzaldehydes Using Knudsen Effusion Mass Spectrometry

Molecular calculations with the nonempirical ab initioMODPOT, VRDDO, and MODPOT/VRDDO procedures. XI. Theoretical study of the [C₆H₅OH ⃛OC₆H₅]⁻ molecular complex: Ab initioMODPOT/VRDDO calculations and electrostatic molecular potential contour maps

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Theoretical study of the hydrogen bonding ability of phenol and its ortho, meta and para substituted derivatives

Cited by 11 publications

References 12 publications

Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Measured Solid State and Sub-Cooled Liquid Vapour Pressures of Benzaldehydes Using Knudsen Effusion Mass Spectrometry

Molecular calculations with the nonempirical ab initioMODPOT, VRDDO, and MODPOT/VRDDO procedures. XI. Theoretical study of the [C6H5OH ⃛OC6H5]− molecular complex: Ab initioMODPOT/VRDDO calculations and electrostatic molecular potential contour maps

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Molecular calculations with the nonempirical ab initioMODPOT, VRDDO, and MODPOT/VRDDO procedures. XI. Theoretical study of the [C₆H₅OH ⃛OC₆H₅]⁻ molecular complex: Ab initioMODPOT/VRDDO calculations and electrostatic molecular potential contour maps