Capturing Fleeting Intermediates in a Claisen Rearrangement Using Nonequilibrium Droplet Imbibition Reaction Conditions

Sahraeian, Taghi; Kulyk, Dmytro S.; Fernandez, Joseph P.; Hadad, Christopher M.; Badu-Tawiah, Abraham K.

doi:10.1021/acs.analchem.2c03268

Capturing Fleeting Intermediates in a Claisen Rearrangement Using Nonequilibrium Droplet Imbibition Reaction Conditions

Journal Article · 17 October 2022 · Analytical Chemistry

DOI:https://doi.org/10.1021/acs.analchem.2c03268· OSTI ID:2422033

Sahraeian, Taghi ^[1]; ^[2]; Fernandez, Joseph P. ^[2]; Hadad, Christopher M. ^[2]; ^[2]

Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States; OSTI
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States

Not provided.

Research Organization:: The Ohio State Univ., Columbus, OH (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0022097

OSTI ID:: 2422033

Journal Information:: Analytical Chemistry, Journal Name: Analytical Chemistry Journal Issue: 43 Vol. 94; ISSN 0003-2700

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (36)

Claisen Rearrangement over the Past Nine Decades Martín Castro, Ana M. Chemical Reviews, Vol. 104, Issue 6 https://doi.org/10.1021/cr020703u	journal	April 2004
Claisen Rearrangements: Insight into Solvent Effects and “on Water” Reactivity from QM/MM Simulations Acevedo, Orlando; Armacost, Kira Journal of the American Chemical Society, Vol. 132, Issue 6 https://doi.org/10.1021/ja908680c	journal	January 2010
Organic Reactions in Microdroplets: Reaction Acceleration Revealed by Mass Spectrometry Yan, Xin; Bain, Ryan M.; Cooks, R. Graham Angewandte Chemie International Edition, Vol. 55, Issue 42 https://doi.org/10.1002/anie.201602270	journal	October 2016
Detailed Unfolding and Folding of Gaseous Ubiquitin Ions Characterized by Electron Capture Dissociation Breuker, Kathrin; Oh, HanBin; Horn, David M. Journal of the American Chemical Society, Vol. 124, Issue 22 https://doi.org/10.1021/ja012267j	journal	June 2002
Über Umlagerung von Phenol‐allyläthern in C‐Allyl‐phenole Claisen, L. Berichte der deutschen chemischen Gesellschaft, Vol. 45, Issue 3 https://doi.org/10.1002/cber.19120450348	journal	October 1912
Hydrophobic acceleration of Diels-Alder reactions Rideout, Darryl C.; Breslow, Ronald Journal of the American Chemical Society, Vol. 102, Issue 26 https://doi.org/10.1021/ja00546a048	journal	December 1980
Picomole-Scale Real-Time Photoreaction Screening: Discovery of the Visible-Light-Promoted Dehydrogenation of Tetrahydroquinolines under Ambient Conditions Chen, Suming; Wan, Qiongqiong; Badu-Tawiah, Abraham K. Angewandte Chemie International Edition, Vol. 55, Issue 32 https://doi.org/10.1002/anie.201603530	journal	June 2016
In-Source Microdroplet Derivatization Using Coaxial Contained-Electrospray Mass Spectrometry for Enhanced Sensitivity in Saccharide Analysis Heiss, Derik R.; Badu-Tawiah, Abraham K. Analytical Chemistry, Vol. 93, Issue 50 https://doi.org/10.1021/acs.analchem.1c02897	journal	December 2021
Droplet Imbibition Enables Nonequilibrium Interfacial Reactions in Charged Microdroplets Sahraeian, Taghi; Kulyk, Dmytro S.; Badu-Tawiah, Abraham K. Langmuir, Vol. 35, Issue 45 https://doi.org/10.1021/acs.langmuir.9b02439	journal	October 2019
Peptide Cross-Linking at Ambient Surfaces by Reactions of Nanosprayed Molecular Cations Badu-Tawiah, Abraham K.; Li, Anyin; Jjunju, Fred P. M. Angewandte Chemie International Edition, Vol. 51, Issue 37, p. 9417-9421 https://doi.org/10.1002/anie.201205044	journal	August 2012
The ortho-Claisen rearrangement of phenyl allyl ethers in trifluoroacetic acid Svanholm, Ulla; Parker, Vernon D. Journal of the Chemical Society, Chemical Communications, Issue 11 https://doi.org/10.1039/C39720000645	journal	January 1972
“On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension Narayan, Sridhar; Muldoon, John; Finn, M. G. Angewandte Chemie International Edition, Vol. 44, Issue 21 https://doi.org/10.1002/anie.200462883	journal	May 2005
Detecting Reaction Intermediates in Liquids on the Millisecond Time Scale Using Desorption Electrospray Ionization Perry, Richard H.; Splendore, Maurizio; Chien, Allis Angewandte Chemie International Edition, Vol. 50, Issue 1 https://doi.org/10.1002/anie.201004861	journal	November 2010
Acid catalysed ortho-Claisen rearrangement of allyl aryl ethers in trifluoroacetic acid Svanholm, Ulla; Parker, Vernon D. Journal of the Chemical Society, Perkin Transactions 2, Issue 2 https://doi.org/10.1039/p29740000169	journal	January 1974
Relating Electrospray Ionization Response to Nonpolar Character of Small Peptides Cech, Nadja B.; Enke, Christie G. Analytical Chemistry, Vol. 72, Issue 13 https://doi.org/10.1021/ac9914869	journal	July 2000
Über C‐Alkylierung (Kernalkylierung) von Phenolen Claisen, L. Angewandte Chemie, Vol. 36, Issue 65 https://doi.org/10.1002/ange.19230366502	journal	September 1923
Detection of the Short-Lived Radical Cation Intermediate in the Electrooxidation of N , N -Dimethylaniline by Mass Spectrometry Brown, Timothy A.; Chen, Hao; Zare, Richard N. Angewandte Chemie International Edition, Vol. 54, Issue 38 https://doi.org/10.1002/anie.201506316	journal	August 2015
What causes aqueous acceleration of the Claisen rearrangement? Cramer, Christopher J.; Truhlar, Donald G. Journal of the American Chemical Society, Vol. 114, Issue 23 https://doi.org/10.1021/ja00049a007	journal	November 1992
Effects of hydration on the Claisen rearrangement of allyl vinyl ether from computer simulations Severance, Daniel L.; Jorgensen, William L. Journal of the American Chemical Society, Vol. 114, Issue 27 https://doi.org/10.1021/ja00053a046	journal	December 1992
An integrated electrocatalytic nESI-MS platform for quantification of fatty acid isomers directly from untreated biofluids Chintalapudi, Kavyasree; Badu-Tawiah, Abraham K. Chemical Science, Vol. 11, Issue 36 https://doi.org/10.1039/D0SC03403G	journal	January 2020
Accelerated C–N Bond Formation in Dropcast Thin Films on Ambient Surfaces Badu-Tawiah, Abraham K.; Campbell, Dahlia I.; Cooks, R. Graham Journal of The American Society for Mass Spectrometry, Vol. 23, Issue 9 https://doi.org/10.1007/s13361-012-0394-y	journal	July 2012
Transient Ru-methyl formate intermediates generated with bifunctional transfer hydrogenation catalysts Perry, R. H.; Brownell, K. R.; Chingin, K. Proceedings of the National Academy of Sciences, Vol. 109, Issue 7 https://doi.org/10.1073/pnas.1118934109	journal	February 2012
Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry Santos, Leonardo Silva; Pavam, Cesar Henrique; Almeida, Wanda P. Angewandte Chemie International Edition, Vol. 43, Issue 33 https://doi.org/10.1002/anie.200460059	journal	August 2004
Claisen rearrangement under chemical-ionization conditions Kadentsev, V. I.; Sokovykh, V. D.; Chizhov, O. S. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 27, Issue 8 https://doi.org/10.1007/BF00925081	journal	August 1978
Chemoselective N‐Alkylation of Indoles in Aqueous Microdroplets Gnanamani, Elumalai; Yan, Xin; Zare, Richard N. Angewandte Chemie International Edition, Vol. 59, Issue 8 https://doi.org/10.1002/anie.201913069	journal	February 2020
Probing the Mechanism of the Heck Reaction with Arene Diazonium Salts by Electrospray Mass and Tandem Mass Spectrometry Sabino, Adão A.; Machado, Angelo H. L.; Correia, Carlos Roque D. Angewandte Chemie International Edition, Vol. 43, Issue 19 https://doi.org/10.1002/anie.200353076	journal	April 2004
Accelerated Reaction Kinetics in Microdroplets: Overview and Recent Developments Wei, Zhenwei; Li, Yangjie; Cooks, R. Graham Annual Review of Physical Chemistry, Vol. 71, Issue 1 https://doi.org/10.1146/annurev-physchem-121319-110654	journal	April 2020
Mass Spectrometry Sampling Under Ambient Conditions with Desorption Electrospray Ionization Takats, Z. Science, Vol. 306, Issue 5695, p. 471-473 https://doi.org/10.1126/science.1104404	journal	October 2004
Combined QM/MM Simulation Study of the Claisen Rearrangement of Allyl Vinyl Ether in Aqueous Solution Gao, Jiali Journal of the American Chemical Society, Vol. 116, Issue 4 https://doi.org/10.1021/ja00083a049	journal	February 1994
Reactions of an aromatic σ,σ-biradical with amino acids and dipeptides in the gas phase Fu, Mingkun; Li, Sen; Archibold, Enada Journal of the American Society for Mass Spectrometry, Vol. 21, Issue 10 https://doi.org/10.1016/j.jasms.2010.06.010	journal	October 2010
An integrated mass spectrometry platform enables picomole-scale real-time electrosynthetic reaction screening and discovery Wan, Qiongqiong; Chen, Suming; Badu-Tawiah, Abraham K. Chemical Science, Vol. 9, Issue 26 https://doi.org/10.1039/C8SC00251G	journal	January 2018
Experimental study of the potential energy surface of the protonated cyclohexene oxide/cyclohexanone system. Isomerization, dissociation, and ion-molecule reactions of the isolated ions in the gas phase Kenttamaa, Hilkka I.; Pachuta, Robin R.; Rothwell, Arlene P. Journal of the American Chemical Society, Vol. 111, Issue 5 https://doi.org/10.1021/ja00187a018	journal	March 1989
Microsampling with a Solid-Phase Extraction Cartridge: Storage and Online Mass Spectrometry Analysis Kulyk, Dmytro S.; Sahraeian, Taghi; Lee, Suji Analytical Chemistry, Vol. 93, Issue 40 https://doi.org/10.1021/acs.analchem.1c02960	journal	September 2021
Transition Structures for the Aromatic Claisen Rearrangements by the Molecular Orbital Method Yamabe, S.; Okumoto, S.; Hayashi, T. The Journal of Organic Chemistry, Vol. 61, Issue 18 https://doi.org/10.1021/jo9522419	journal	January 1996
Monoacylation of Symmetrical Diamines in Charge Microdroplets Ansu-Gyeabourh, Emelia; Amoah, Enoch; Ganesa, Chandrashekar Journal of the American Society for Mass Spectrometry, Vol. 32, Issue 2 https://doi.org/10.1021/jasms.0c00384	journal	December 2020
Acceleration of reaction in charged microdroplets Lee, Jae Kyoo; Banerjee, Shibdas; Nam, Hong Gil Quarterly Reviews of Biophysics, Vol. 48, Issue 4 https://doi.org/10.1017/S0033583515000086	journal	July 2015

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