A Strong Acid that does not Protonate Water Full article
Journal |
The Journal of Physical Chemistry A
ISSN: 1089-5639 , E-ISSN: 1520-5215 |
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Output data | Year: 2004, Volume: 108, Number: 42, Pages: 9310-9315 Pages count : 6 DOI: 10.1021/jp047409l | ||||
Tags | TRIFLUOROMETHANE; SULFONIC ACID; INFRARED-SPECTRA; HYDRONIUM ION; HYDROGEN-BOND; SPECTROSCOPY; STRENGTH; BENZENE | ||||
Authors |
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Affiliations |
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Funding (1)
1 | National Institutes of Health | GM 23851 |
Abstract:
The nature of solvated acids in benzene and chlorinated hydrocarbon solvents is sensitively revealed by IR spectroscopy. Two similarly strong, structurally related acids, triflic acid (CF3SO3H) and the N−H acid bis(trifluoromethylsulfonyl) imide ((CF3SO2)2NH), behave quite differently toward water in these media. Triflic acid protonates water at the one-equivalent level to give the hydronium ion, H3O+. By contrast, bis(trifluoromethylsulfonyl) imide forms a simple hydrate, (CF3SO2)2NH···OH2, even with water at the two-equivalent level. The difference arises from the differing abilities of the conjugate base anions to engage in H-bonding and ion pairing. It illustrates how acidity in low-dielectric media is critically dependent on the nature of the conjugate base anion. νO−H and νN−H stretching frequencies indicate that the H-bonding acceptor ability for solvents toward acidic protons increases in the order carbon tetrachloride < benzene ∼ 1,2-dichoroethane < water. With benzene, a marked tendency for acidic protons to H-bond to the π-face of the arene ring is noted and an IR signature of this solvation mode is observed.
Cite:
Stoyanov E.S.
, Kim K-C.
, Reed C.A.
A Strong Acid that does not Protonate Water
The Journal of Physical Chemistry A. 2004. V.108. N42. P.9310-9315. DOI: 10.1021/jp047409l WOS Scopus РИНЦ
A Strong Acid that does not Protonate Water
The Journal of Physical Chemistry A. 2004. V.108. N42. P.9310-9315. DOI: 10.1021/jp047409l WOS Scopus РИНЦ
Files:
Full text from publisher
Dates:
Submitted: | Jun 15, 2004 |
Accepted: | Aug 5, 2004 |
Published online: | Sep 21, 2004 |
Published print: | Oct 1, 2004 |
Identifiers:
Web of science | WOS:000224538900040 |
Scopus | 2-s2.0-7544222924 |
Elibrary | 13471957 |
Chemical Abstracts | 2004:769898 |
Chemical Abstracts (print) | 141:365935 |
OpenAlex | W2000114278 |