The ortho-dehydrophenoxy anion: an unusual ion formed from a surprising reaction

Gregg D. Dahlke; Steven R. Kass

doi:10.1016/0168-1176(92)80117-J

The ortho-dehydrophenoxy anion: an unusual ion formed from a surprising reaction

Gregg D. Dahlke, Steven R. Kass

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The conjugate bases of fluorobenzene and methoxybenzene react with nitrous oxide to afford the dehydrophenoxy anion (C₆H₃O^-). The mechanism for the formation of this novel ion has been explored as has some if its reactivity. In general, the reactions of C₆H₃O^- proceed via proton transfer, addition of the newly formed anion to the benzyne triple bond, and subsequent fragmentation. Acidities of the different ring positions in methoxybenzene are also reported.

Original language	English (US)
Pages (from-to)	633-645
Number of pages	13
Journal	International Journal of Mass Spectrometry and Ion Processes
Volume	117
Issue number	C
DOIs	https://doi.org/10.1016/0168-1176(92)80117-J
State	Published - Sep 1 1992

Bibliographical note

Funding Information:
The kindnessa nd generosityo f ProfessorC .H. DePuy, in whosel aboratory the first observationsre portedi n this studyw erem ade,i s gratefullya cknow-ledged. Generous allocations of computer resourcesf rom the Minnesota SupercomputerIn stitute and financial support from the National Science Foundation (CHE-8907198)a nd the donors of the Petroleum Research Foundation, as administeredb y the American Chemical Society, are also appreciated.

Keywords

Gas phase
flowing afterglow
fluorobenzene
methoxybenzene
ortho-dehydrophenoxy anion

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10.1016/0168-1176(92)80117-J

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title = "The ortho-dehydrophenoxy anion: an unusual ion formed from a surprising reaction",

abstract = "The conjugate bases of fluorobenzene and methoxybenzene react with nitrous oxide to afford the dehydrophenoxy anion (C6H3O-). The mechanism for the formation of this novel ion has been explored as has some if its reactivity. In general, the reactions of C6H3O- proceed via proton transfer, addition of the newly formed anion to the benzyne triple bond, and subsequent fragmentation. Acidities of the different ring positions in methoxybenzene are also reported.",

keywords = "Gas phase, flowing afterglow, fluorobenzene, methoxybenzene, ortho-dehydrophenoxy anion",

author = "Dahlke, {Gregg D.} and Kass, {Steven R.}",

note = "Funding Information: The kindnessa nd generosityo f ProfessorC .H. DePuy, in whosel aboratory the first observationsre portedi n this studyw erem ade,i s gratefullya cknow-ledged. Generous allocations of computer resourcesf rom the Minnesota SupercomputerIn stitute and financial support from the National Science Foundation (CHE-8907198)a nd the donors of the Petroleum Research Foundation, as administeredb y the American Chemical Society, are also appreciated.",

year = "1992",

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doi = "10.1016/0168-1176(92)80117-J",

language = "English (US)",

volume = "117",

pages = "633--645",

journal = "International Journal of Mass Spectrometry and Ion Processes",

issn = "0168-1176",

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TY - JOUR

T1 - The ortho-dehydrophenoxy anion

T2 - an unusual ion formed from a surprising reaction

AU - Dahlke, Gregg D.

AU - Kass, Steven R.

N1 - Funding Information: The kindnessa nd generosityo f ProfessorC .H. DePuy, in whosel aboratory the first observationsre portedi n this studyw erem ade,i s gratefullya cknow-ledged. Generous allocations of computer resourcesf rom the Minnesota SupercomputerIn stitute and financial support from the National Science Foundation (CHE-8907198)a nd the donors of the Petroleum Research Foundation, as administeredb y the American Chemical Society, are also appreciated.

PY - 1992/9/1

Y1 - 1992/9/1

N2 - The conjugate bases of fluorobenzene and methoxybenzene react with nitrous oxide to afford the dehydrophenoxy anion (C6H3O-). The mechanism for the formation of this novel ion has been explored as has some if its reactivity. In general, the reactions of C6H3O- proceed via proton transfer, addition of the newly formed anion to the benzyne triple bond, and subsequent fragmentation. Acidities of the different ring positions in methoxybenzene are also reported.

AB - The conjugate bases of fluorobenzene and methoxybenzene react with nitrous oxide to afford the dehydrophenoxy anion (C6H3O-). The mechanism for the formation of this novel ion has been explored as has some if its reactivity. In general, the reactions of C6H3O- proceed via proton transfer, addition of the newly formed anion to the benzyne triple bond, and subsequent fragmentation. Acidities of the different ring positions in methoxybenzene are also reported.

KW - Gas phase

KW - flowing afterglow

KW - fluorobenzene

KW - methoxybenzene

KW - ortho-dehydrophenoxy anion

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DO - 10.1016/0168-1176(92)80117-J

M3 - Article

AN - SCOPUS:0009091442

SN - 0168-1176

VL - 117

SP - 633

EP - 645

JO - International Journal of Mass Spectrometry and Ion Processes

JF - International Journal of Mass Spectrometry and Ion Processes

IS - C

ER -

The ortho-dehydrophenoxy anion: an unusual ion formed from a surprising reaction

Abstract

Bibliographical note

Keywords

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