Conformational preferences of a polar biaryl: A phase- and enantiomeric purity-dependent molecular hinge

Jonathan Clayden; Stephen P. Fletcher; S. J M Rowbottom; Madeleine Helliwell

doi:10.1021/ol9006635

Conformational preferences of a polar biaryl: A phase- and enantiomeric purity-dependent molecular hinge

Jonathan Clayden^*, Stephen P. Fletcher, S. J M Rowbottom, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

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

12 Citations (Scopus)

Abstract

The favored (RS*,M*) diastereoisomer of 2-aryl-pyridine 1 in the solution state results from intramolecular dipole-dipole interactions. In the crystalline state, intermolecular interactions dominate, and the conformation switches reversibly to (RS*,P*). Only racemic 1 exhibits this switching property: enantiomerically pure 1 exists as the (RS*,M*) diastereoisomer in both the solution and crystalline state.

Original language	English
Pages (from-to)	2313-2316
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	11
Early online date	12 May 2009
DOIs	https://doi.org/10.1021/ol9006635
Publication status	Published - 4 Jun 2009

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Organic & Biological

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title = "Conformational preferences of a polar biaryl: A phase- and enantiomeric purity-dependent molecular hinge",

abstract = "The favored (RS*,M*) diastereoisomer of 2-aryl-pyridine 1 in the solution state results from intramolecular dipole-dipole interactions. In the crystalline state, intermolecular interactions dominate, and the conformation switches reversibly to (RS*,P*). Only racemic 1 exhibits this switching property: enantiomerically pure 1 exists as the (RS*,M*) diastereoisomer in both the solution and crystalline state.",

author = "Jonathan Clayden and Fletcher, \{Stephen P.\} and Rowbottom, \{S. J M\} and Madeleine Helliwell",

year = "2009",

month = jun,

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doi = "10.1021/ol9006635",

language = "English",

volume = "11",

pages = "2313--2316",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Conformational preferences of a polar biaryl

T2 - A phase- and enantiomeric purity-dependent molecular hinge

AU - Clayden, Jonathan

AU - Fletcher, Stephen P.

AU - Rowbottom, S. J M

AU - Helliwell, Madeleine

PY - 2009/6/4

Y1 - 2009/6/4

N2 - The favored (RS*,M*) diastereoisomer of 2-aryl-pyridine 1 in the solution state results from intramolecular dipole-dipole interactions. In the crystalline state, intermolecular interactions dominate, and the conformation switches reversibly to (RS*,P*). Only racemic 1 exhibits this switching property: enantiomerically pure 1 exists as the (RS*,M*) diastereoisomer in both the solution and crystalline state.

AB - The favored (RS*,M*) diastereoisomer of 2-aryl-pyridine 1 in the solution state results from intramolecular dipole-dipole interactions. In the crystalline state, intermolecular interactions dominate, and the conformation switches reversibly to (RS*,P*). Only racemic 1 exhibits this switching property: enantiomerically pure 1 exists as the (RS*,M*) diastereoisomer in both the solution and crystalline state.

UR - https://www.scopus.com/pages/publications/66149161664

U2 - 10.1021/ol9006635

DO - 10.1021/ol9006635

M3 - Article (Academic Journal)

C2 - 19435372

AN - SCOPUS:66149161664

SN - 1523-7060

VL - 11

SP - 2313

EP - 2316

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Conformational preferences of a polar biaryl: A phase- and enantiomeric purity-dependent molecular hinge

Abstract

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