Acidities and basicities of carboxylic acids. Correlations between core-ionization energies, proton affinities, and gas-phase acidities

Smith, S. R.; Thomas, T. D.

doi:10.1021/ja00485a033

Cited by 66 publications

(35 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is not surprising since the 0 1 s binding energies used in their leastsquares fit were taken from ref. 3.…”

Section: Core Binding Energies and Gas Phase Aciditiesmentioning

confidence: 99%

“…Furthermore, eqs. [2] and [3] suggest a correlation between EB and PA. These results will be used in the present work to calculate a number of interesting quantities.…”

Section: Introductionmentioning

confidence: 98%

“…Although carboxylic acids have been studied rather extensively by X-ray photoelectron spectroscopy (XPS) (1)(2)(3) there are to date no available core binding energy data on aromatic acids. The reason is primarily the lack of volatility of these species.…”

Section: Introductionmentioning

confidence: 99%

“…Thus this quantity is the PA of the anion. For gas phase acidities, A , we have (3,8) It can therefore be seen that combining eqs. [2] and [5] can yield A V and AR.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The core binding energies of some gaseous aromatic carboxylic acids and their relationship to profon affinities and gas phase acidities

McQuaide¹,

Banna²

1988

Can. J. Chem.

View full text Add to dashboard Cite

The C 1s and O 1s core binding energies of gaseous benzoic, phthalic, isophthalic, and terephthalic acids have been measured by X-ray photoelectron spectroscopy. The π-donor relaxation energies associated with the carbonyl oxygen ionization in these systems have been found to be around 2 eV, close to the value for acetic acid. Comparison of the O 1s binding energies in phenol and benzoic acid with the gas phase acidities shows that the increased acidity of benzoic acid is attributable mostly to initial-state inductive effects. A number of O 1s – proton affinity correlations have been used to predict proton affinities for these acids. It is found that benzoic acid is the strongest base and the weakest acid.

show abstract

“…This is not surprising since the 0 1 s binding energies used in their leastsquares fit were taken from ref. 3.…”

Section: Core Binding Energies and Gas Phase Aciditiesmentioning

confidence: 99%

“…Furthermore, eqs. [2] and [3] suggest a correlation between EB and PA. These results will be used in the present work to calculate a number of interesting quantities.…”

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

“…Thus this quantity is the PA of the anion. For gas phase acidities, A , we have (3,8) It can therefore be seen that combining eqs. [2] and [5] can yield A V and AR.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The core binding energies of some gaseous aromatic carboxylic acids and their relationship to profon affinities and gas phase acidities

McQuaide¹,

Banna²

1988

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…Their core electron binding energies have been determined in the X-ray photoelectron spectroscopy (XPS). 8) Based on the present band-deconvolution analysis and previous band assignments for other esters, we assigned the O1s excitation bands for the TIY as listed in Table 1. Two intense bands below the ionization edges occur at energies 531.9 eV (O1s CO !…”

Section: Methodsmentioning

confidence: 97%

Site- and State-Selective Dissociation of Core-Excited Organic Molecules: Deuterium-Labeled Methyl Acetate

Kawasaki

Yamanaka

Tabayashi

et al. 2008

Journal of Nuclear Science and Technology

View full text Add to dashboard Cite

Site-and state-selective dissociation of methyl acetate induced by core level excitation has been studied in the oxygen K-edge region using time-of-flight fragment-mass spectroscopy. O1s core (C=O/OMe) to valence (C{OMe ) excitation bands in the total-ion-yields of methyl acetate were assigned based on the comparison with those of other esters and band-deconvolution analysis. Product branching ratios of CD 3 þ and CDO þ cations from deuterium-labeled methyl-d 3 acetate (CH 3 C(O)OCD 3 ) showed that site-selective bond scission takes place between the (O1s CO À1 Ã CO ) and (O1s OMe À1 Ã CO ) sites, indicating the dissociation with an antibonding nature after the spectator Auger transitions. Although the efficient production of CDO þ was observed at the (O1s OMe À1 Ã C{OMe ) transition, however, no apparent state-selective dissociation of CD 3 þ could be observed at the (O1s OMe À1 Ã O{Me ). The present results indicate that the lack of state-selectivity at the (O1s OMe À1 Ã O{Me ) is largely due to the weak band intensity buried into the congestion of core-to-Rydberg transitions.

show abstract

Electronic Substituent Effects in Molecular Spectroscopy

Topsom

1987

Progress in Physical Organic Chemistry

View full text Add to dashboard Cite

Acidities and basicities of carboxylic acids. Correlations between core-ionization energies, proton affinities, and gas-phase acidities

Cited by 66 publications

References 4 publications

The core binding energies of some gaseous aromatic carboxylic acids and their relationship to profon affinities and gas phase acidities

The core binding energies of some gaseous aromatic carboxylic acids and their relationship to profon affinities and gas phase acidities

Site- and State-Selective Dissociation of Core-Excited Organic Molecules: Deuterium-Labeled Methyl Acetate

Electronic Substituent Effects in Molecular Spectroscopy

Contact Info

Product

Resources

About