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Literature DB >> 24339386

The strongest Brønsted acid: protonation of alkanes by H(CHB(11)F(11)) at room temperature.

Matthew Nava¹, Irina V Stoyanova, Steven Cummings, Evgenii S Stoyanov, Christopher A Reed.

Abstract

What is the strongest acid? Can a simple Brønsted acid be prepared that can protonate an alkane at room temperature? Can that acid be free of the complicating effects of added Lewis acids that are typical of common, difficult-to-handle superacid mixtures? The carborane superacid H(CHB11 F11 ) is that acid. It is an extremely moisture-sensitive solid, prepared by treatment of anhydrous HCl with [Et3 SiHSiEt3 ][CHB11 F11 ]. It adds H2 O to form [H3 O][CHB11 F11 ] and benzene to form the benzenium ion salt [C6 H7 ][CHB11 F11 ]. It reacts with butane to form a crystalline tBu(+) salt and with n-hexane to form an isolable hexyl carbocation salt. Carbocations, which are thus no longer transient intermediates, react with NaH either by hydride addition to re-form an alkane or by deprotonation to form an alkene and H2 . By protonating alkanes at room temperature, the reactivity of H(CHB11 F11 ) opens up new opportunities for the easier study of acid-catalyzed hydrocarbon reforming.

Entities: CellLine Chemical Disease Gene

Keywords: Brønsted acids; carbocations; carboranes; hydrocarbons

Year: 2013 PMID： 24339386 PMCID： PMC4993161 DOI： 10.1002/anie.201308586

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

18 in total

3. The Chloronium Cation [(C₂H₃)₂Cl⁺] and Unsaturated C₄-Carbocations with C=C and C≡C Bonds in Their Solid Salts and in Solutions: An H¹/C¹³ NMR and Infrared Spectroscopic Study.

Authors: Evgenii S Stoyanov; Irina V Stoyanova
Journal: Int J Mol Sci Date: 2022-08-14 Impact factor: 6.208

3 in total

The strongest Brønsted acid: protonation of alkanes by H(CHB(11)F(11)) at room temperature.

1. Putting tert-butyl cation in a bottle.

2. The strongest isolable acid.

3. H(+), CH(3)(+), and R(3)Si(+) carborane reagents: when triflates fail.

4. An infrared nuNH scale for weakly basic anions. Implications for single-molecule acidity and superacidity.

5. Oligomeric carbocation-like species from protonation of chloroalkanes.

6. Evidence for C-H hydrogen bonding in salts of tert-butyl cation.

7. Superacidity of boron acids H2(B12X12) (X = Cl, Br).

8. Novel weak coordination to silylium ions: formation of nearly linear Si-H-Si bonds.

9. The structure of the strongest Brønsted acid: the carborane acid H(CHB11Cl11).

10. Gas-phase Brønsted superacidity of some derivatives of monocarba-closo-borates: a computational study.

1. Myths about the proton. The nature of H+ in condensed media.

2. IR-Spectroscopic and X-ray-Structural Study of Vinyl-Type Carbocations in Their Carborane Salts.

3. The Chloronium Cation [(C₂H₃)₂Cl⁺] and Unsaturated C₄-Carbocations with C=C and C≡C Bonds in Their Solid Salts and in Solutions: An H¹/C¹³ NMR and Infrared Spectroscopic Study.