Literature DB >> 28194736

Fischer Indole Synthesis in the Gas Phase, the Solution Phase, and at the Electrospray Droplet Interface.

Ryan M Bain1, Stephen T Ayrton1, R Graham Cooks2.   

Abstract

Previous reports have shown that reactions occurring in the microdroplets formed during electrospray ionization can, under the right conditions, exhibit significantly greater rates than the corresponding bulk solution-phase reactions. The observed acceleration under electrospray ionization could result from a solution-phase, a gas-phase, or an interfacial reaction. This study shows that a gas-phase ion/molecule (or ion/ion) reaction is not responsible for the observed rate enhancement in the particular case of the Fischer indole synthesis. The results show that the accelerated reaction proceeds in the microdroplets, and evidence is provided that an interfacial process is involved. Graphical Abstract <!-- [INSERT GRAPHICAL ABSTRACT TEXT HERE] -->.

Entities:  

Keywords:  Accelerated reactions; Electrospray; Fischer indole synthesis

Year:  2017        PMID: 28194736     DOI: 10.1007/s13361-017-1597-z

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN: 1044-0305            Impact factor:   3.109


  31 in total

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Authors:  Yousung Jung; R A Marcus
Journal:  J Am Chem Soc       Date:  2007-03-28       Impact factor: 15.419

2.  Ion formation from charged droplets: Roles of geometry, energy, and time.

Authors:  J B Fenn
Journal:  J Am Soc Mass Spectrom       Date:  1993-07       Impact factor: 3.109

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Authors:  M Wilm; M Mann
Journal:  Anal Chem       Date:  1996-01-01       Impact factor: 6.986

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5.  Accelerated carbon-carbon bond-forming reactions in preparative electrospray.

Authors:  Thomas Müller; Abraham Badu-Tawiah; R Graham Cooks
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-08       Impact factor: 15.336

6.  Accelerated C-N bond formation in dropcast thin films on ambient surfaces.

Authors:  Abraham K Badu-Tawiah; Dahlia I Campbell; R Graham Cooks
Journal:  J Am Soc Mass Spectrom       Date:  2012-07-24       Impact factor: 3.109

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Authors:  Elizabeth A Crawford; Cemal Esen; Dietrich A Volmer
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8.  The Role of the Interface in Thin Film and Droplet Accelerated Reactions Studied by Competitive Substituent Effects.

Authors:  Yafeng Li; Xin Yan; R Graham Cooks
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-05       Impact factor: 15.336

9.  On-Tissue Derivatization via Electrospray Deposition for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry Imaging of Endogenous Fatty Acids in Rat Brain Tissues.

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Journal:  Anal Chem       Date:  2016-05-26       Impact factor: 6.986

Review 10.  Acceleration of reaction in charged microdroplets.

Authors:  Jae Kyoo Lee; Shibdas Banerjee; Hong Gil Nam; Richard N Zare
Journal:  Q Rev Biophys       Date:  2015-11       Impact factor: 5.318

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  6 in total

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Authors:  Hilary M Brown; Karan R Doppalapudi; Patrick W Fedick
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5.  Accelerated microdroplet synthesis of benzimidazoles by nucleophilic addition to protonated carboxylic acids.

Authors:  Pallab Basuri; L Edwin Gonzalez; Nicolás M Morato; Thalappil Pradeep; R Graham Cooks
Journal:  Chem Sci       Date:  2020-07-14       Impact factor: 9.825

6.  A critical analysis of electrospray techniques for the determination of accelerated rates and mechanisms of chemical reactions in droplets.

Authors:  Grazia Rovelli; Michael I Jacobs; Megan D Willis; Rebecca J Rapf; Alexander M Prophet; Kevin R Wilson
Journal:  Chem Sci       Date:  2020-10-26       Impact factor: 9.825

  6 in total

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