trans Deformation of a Carbon-Carbon Triple Bond in Response to Incipient Nucleophilic Attack

The X-Ray Crystal Structure of Ethyl 3-(2-Nitrophenyl)propynoate at 150 K

Craig R. Rice, John D. Wallis

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.

Original languageEnglish
Pages (from-to)572-574
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number6
DOIs
Publication statusPublished - 1993
Externally publishedYes

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Alkynes
Carbon
Crystal structure
X-Rays
Electrons
X rays
Nucleophiles
Atoms

Cite this

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title = "trans Deformation of a Carbon-Carbon Triple Bond in Response to Incipient Nucleophilic Attack: The X-Ray Crystal Structure of Ethyl 3-(2-Nitrophenyl)propynoate at 150 K",
abstract = "In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.",
author = "Rice, {Craig R.} and Wallis, {John D.}",
year = "1993",
doi = "10.1039/C39930000572",
language = "English",
pages = "572--574",
journal = "Chemical Communications",
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publisher = "Royal Society of Chemistry",
number = "6",

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T2 - The X-Ray Crystal Structure of Ethyl 3-(2-Nitrophenyl)propynoate at 150 K

AU - Rice, Craig R.

AU - Wallis, John D.

PY - 1993

Y1 - 1993

N2 - In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.

AB - In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.

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U2 - 10.1039/C39930000572

DO - 10.1039/C39930000572

M3 - Article

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JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

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