The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect

David O'Hagan; C Bilton; JAK Howard; L Knight; DJ Tozer

doi:10.1039/B000205O

The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect

David O'Hagan, C Bilton, JAK Howard, L Knight, DJ Tozer

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

Abstract

Experimental and theoretical data indicate a preferred conformation for N-beta-fluoroethylamides in which the C-F and C-N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol(-1) lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol(-1) for the gauche effect in 1,2-difluoroethane.

Original language	English
Pages (from-to)	605-607
Number of pages	3
Journal	Journal of Chemical Society, Perkin Transactions 2
Issue number	4
DOIs	https://doi.org/10.1039/B000205O
Publication status	Published - 2000

Keywords

1,2-DIFLUOROETHANE

Access to Document

10.1039/B000205O

Cite this

@article{c26244b7f6f1431b8bee87e7d7286afd,

title = "The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect",

abstract = "Experimental and theoretical data indicate a preferred conformation for N-beta-fluoroethylamides in which the C-F and C-N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol(-1) lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol(-1) for the gauche effect in 1,2-difluoroethane.",

keywords = "1,2-DIFLUOROETHANE",

author = "David O'Hagan and C Bilton and JAK Howard and L Knight and DJ Tozer",

year = "2000",

doi = "10.1039/B000205O",

language = "English",

pages = "605--607",

journal = "Journal of Chemical Society, Perkin Transactions 2",

issn = "1470-1820",

publisher = "Royal Society of Chemistry",

number = "4",

}

TY - JOUR

T1 - The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect

AU - O'Hagan, David

AU - Bilton, C

AU - Howard, JAK

AU - Knight, L

AU - Tozer, DJ

PY - 2000

Y1 - 2000

N2 - Experimental and theoretical data indicate a preferred conformation for N-beta-fluoroethylamides in which the C-F and C-N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol(-1) lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol(-1) for the gauche effect in 1,2-difluoroethane.

AB - Experimental and theoretical data indicate a preferred conformation for N-beta-fluoroethylamides in which the C-F and C-N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol(-1) lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol(-1) for the gauche effect in 1,2-difluoroethane.

KW - 1,2-DIFLUOROETHANE

UR - http://www.scopus.com/inward/record.url?scp=0034175168&partnerID=8YFLogxK

U2 - 10.1039/B000205O

DO - 10.1039/B000205O

M3 - Article

SN - 1470-1820

SP - 605

EP - 607

JO - Journal of Chemical Society, Perkin Transactions 2

JF - Journal of Chemical Society, Perkin Transactions 2

IS - 4

ER -

The preferred conformation of N-β-fluoroethylamides.Observation of the fluorine amide gauche effect

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this