PH-dependent conformational switching in 2,6-benzamidodiphenylacetylenes

Ian M. Jones; Hannah Lingard; Andrew D. Hamilton

doi:10.1002/anie.201106241

PH-dependent conformational switching in 2,6-benzamidodiphenylacetylenes

Ian M. Jones, Hannah Lingard, Andrew D. Hamilton

Chemistry

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

Abstract

The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.

Original language	English (US)
Pages (from-to)	12569-12571
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	52
DOIs	https://doi.org/10.1002/anie.201106241
State	Published - Dec 23 2011

Keywords

conformational dynamics
diphenylacetylene
hydrogen bonding
molecular switch
pH dependence

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201106241

Cite this

@article{e76253d295e14057bd576ac8f26f2422,

title = "PH-dependent conformational switching in 2,6-benzamidodiphenylacetylenes",

abstract = "The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.",

keywords = "conformational dynamics, diphenylacetylene, hydrogen bonding, molecular switch, pH dependence",

author = "Jones, {Ian M.} and Hannah Lingard and Hamilton, {Andrew D.}",

year = "2011",

month = dec,

day = "23",

doi = "10.1002/anie.201106241",

language = "English (US)",

volume = "50",

pages = "12569--12571",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "52",

}

TY - JOUR

T1 - PH-dependent conformational switching in 2,6-benzamidodiphenylacetylenes

AU - Jones, Ian M.

AU - Lingard, Hannah

AU - Hamilton, Andrew D.

PY - 2011/12/23

Y1 - 2011/12/23

N2 - The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.

AB - The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.

KW - conformational dynamics

KW - diphenylacetylene

KW - hydrogen bonding

KW - molecular switch

KW - pH dependence

UR - http://www.scopus.com/inward/record.url?scp=84255162371&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84255162371&partnerID=8YFLogxK

U2 - 10.1002/anie.201106241

DO - 10.1002/anie.201106241

M3 - Article

C2 - 22173825

AN - SCOPUS:84255162371

SN - 1433-7851

VL - 50

SP - 12569

EP - 12571

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

PH-dependent conformational switching in 2,6-benzamidodiphenylacetylenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this