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Protonated p-Benzoquinone

Journal Article · · Journal of Organic Chemistry
DOI:https://doi.org/10.1021/jo951580z· OSTI ID:494237
; ;  [1]
  1. National Inst. of Standards and Technology, Gaithersburg, MD (United States); and others
The structure and energetics of protonated p-benzoquinone (pBQ) have been investigated using high-pressure mass spectrometry and ab initio calculations. The experimental proton affinity of pBQ is 801-4 {plus_minus} kJ/mol (191.5 {plus_minus} 2.1 kcal/mol) (1{sigma}) from bracketing measurements and hydration thermochemistry. This value is supported by theory and by analogies with related compounds. In its protonation chemistry, pBQ behaves as an aliphatic ketone, both structurally and energetically. The dissociation of the hydrate (pBQH{sup +}){center_dot}(H{sub 2}O) is characterized by {delta}H{sup o}{sub D} = 90.0 {plus_minus} 2.3 kJ/mol and {delta}S{sup o}{sub D} = 123.4 {plus_minus} 4.9 J/mol{center_dot}K (95% confidence). 3 tabs., 1 fig.
OSTI ID:
494237
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 9 Vol. 61; ISSN 0022-3263; ISSN JOCEAH
Country of Publication:
United States
Language:
English

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