Literature DB >> 22887067

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

Evgenii S Stoyanov1, Irina V Stoyanova, Fook S Tham, Christopher A Reed.   

Abstract

Environmentally sensitive: A combination of C-H anion hydrogen bonding and hyperconjugative charge delocalization explains the sensitivity of the IR spectrum of the tert-butyl cation to its anion (see high-resolution X-ray structure with a CHB(11)Cl(11)(-) counterion). The νCH vibration of the cation scales linearly with the basicity of carborane anions on the νNH scale. The same also holds for the C(6)H(7)(+) benzenium ion.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22887067      PMCID： PMC3516884          DOI： 10.1002/anie.201203958

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


  11 in total

1.  Putting tert-butyl cation in a bottle.

Authors:  Tsuyoshi Kato; Christopher A Reed
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-24       Impact factor: 15.336

2.  Structures and energetics of the tert-butyl cation: the final answer or a never-ending story?

Authors:  Hao Feng; Weiguo Sun; Yaoming Xie; Henry F Schaefer
Journal:  Chemistry       Date:  2011-09-12       Impact factor: 5.236

3.  Nonclassical carbocations as C-H hydrogen bond donors.

Authors:  Mihaela D Bojin; Dean J Tantillo
Journal:  J Phys Chem A       Date:  2006-04-13       Impact factor: 2.781

4.  Infrared spectroscopy of the tert-butyl cation in the gas phase.

Authors:  Gary E Douberly; Allen M Ricks; Brian W Ticknor; Paul v R Schleyer; Michael A Duncan
Journal:  J Am Chem Soc       Date:  2007-10-18       Impact factor: 15.419

5.  Ab initio/DFT/GIAO-CCSD(T) calculational study of the t-butyl cation: comparison of experimental data with structures, energetics, IR vibrational frequencies, and 13C NMR chemical shifts indicating preferred C(s) conformation.

Authors:  Golam Rasul; Jonathan L Chen; G K Surya Prakash; George A Olah
Journal:  J Phys Chem A       Date:  2009-06-18       Impact factor: 2.781

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

Authors:  Christopher A Reed
Journal:  Acc Chem Res       Date:  2010-01-19       Impact factor: 22.384

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

Authors:  Evgenii S Stoyanov; Kee-Chan Kim; Christopher A Reed
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

8.  Dialkyl chloronium ions.

Authors:  Evgenii S Stoyanov; Irina V Stoyanova; Fook S Tham; Christopher A Reed
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

9.  Isolating benzenium ion salts.

Authors:  Christopher A Reed; Kee-Chan Kim; Evgenii S Stoyanov; Daniel Stasko; Fook S Tham; Leonard J Mueller; Peter D W Boyd
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

10.  IR spectroscopic properties of H(MeOH)n + clusters in the liquid phase: evidence for a proton wire.

Authors:  Evgenii S Stoyanov; Irina V Stoyanova; Christopher A Reed
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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  3 in total

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

Authors:  Matthew Nava; Irina V Stoyanova; Steven Cummings; Evgenii S Stoyanov; Christopher A Reed
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-11       Impact factor: 15.336

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

Authors:  Christopher A Reed
Journal:  Acc Chem Res       Date:  2013-07-23       Impact factor: 22.384

3.  Reactive p-block cations stabilized by weakly coordinating anions.

Authors:  Tobias A Engesser; Martin R Lichtenthaler; Mario Schleep; Ingo Krossing
Journal:  Chem Soc Rev       Date:  2015-11-27       Impact factor: 54.564
  3 in total

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