Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides

Mark S. Betson; Jonathan Clayden; Ho Kam Lam; Madeleine Helliwell

doi:10.1002/anie.200461787

Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides

Mark S. Betson^*, Jonathan Clayden, Ho Kam Lam, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

21 Citations (Scopus)

Abstract

Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO₂R, SO₂R) interact with the dipole of both amides to yield a syn orientation (see picture).

Original language	English
Pages (from-to)	1241-1244
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	8
Early online date	14 Jan 2005
DOIs	https://doi.org/10.1002/anie.200461787
Publication status	Published - 11 Feb 2005

Research Groups and Themes

Organic & Biological

Keywords

Amides
Conformation analysis
Dipoles
Electrostatic interactions

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title = "Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides",

abstract = "Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO2R, SO2R) interact with the dipole of both amides to yield a syn orientation (see picture).",

keywords = "Amides, Conformation analysis, Dipoles, Electrostatic interactions",

author = "Betson, \{Mark S.\} and Jonathan Clayden and Lam, \{Ho Kam\} and Madeleine Helliwell",

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AU - Betson, Mark S.

AU - Clayden, Jonathan

AU - Lam, Ho Kam

AU - Helliwell, Madeleine

PY - 2005/2/11

Y1 - 2005/2/11

N2 - Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO2R, SO2R) interact with the dipole of both amides to yield a syn orientation (see picture).

AB - Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO2R, SO2R) interact with the dipole of both amides to yield a syn orientation (see picture).

KW - Amides

KW - Conformation analysis

KW - Dipoles

KW - Electrostatic interactions

UR - https://www.scopus.com/pages/publications/15444373635

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DO - 10.1002/anie.200461787

M3 - Article (Academic Journal)

AN - SCOPUS:15444373635

SN - 1433-7851

VL - 44

SP - 1241

EP - 1244

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 8

ER -

Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides

Abstract

Research Groups and Themes

Keywords

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