Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

Thomas Adler; Josep Bonjoch; Jonathan Clayden; Mercè Font-Bardía; Mark Pickworth; Xavier Solans; Daniel Solé; Lluís Vallverdú

doi:10.1039/b507202f

Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

Thomas Adler
, Josep Bonjoch
, Jonathan Clayden
, Mercè Font-Bardía
, Mark Pickworth
, Xavier Solans
, Daniel Solé
, Lluís Vallverdú

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

Abstract

N-Acylated 2-substituted anilines undergo slow Ar-N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar-N bond rotation by NMR. 2-Iodoanilides bearing a branched N-substituent demonstrate sufficient enantiomeric stability to be resolvable, either by HPLC or by formation of diastereoisomeric lactanilide derivatives. For the first time, the rates of Ar-N rotation in 2-substituted N,N-diarylureas have been established: they mainly fall in the region of 50-70 kJ mol-1 with a relatively weak dependence on substituent size. © The Royal Society of Chemistry 2005.

Original language	English
Pages (from-to)	3173-3183
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	3
Issue number	17
DOIs	https://doi.org/10.1039/b507202f
Publication status	Published - 7 Sept 2005

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10.1039/b507202f

CCDC 273163: Experimental Crystal Structure Determination
Adler, T. (Contributor), Bonjoch, J. (Contributor), Clayden, J. (Contributor), Font-Bardía, M. (Contributor), Pickworth, M. (Contributor), Solans, X. (Contributor), Solé, D. (Contributor) & Vallverdú, L. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2006
DOI: 10.5517/cc957qd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc957qd&sid=DataCite
Dataset

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title = "Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines",

abstract = "N-Acylated 2-substituted anilines undergo slow Ar-N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar-N bond rotation by NMR. 2-Iodoanilides bearing a branched N-substituent demonstrate sufficient enantiomeric stability to be resolvable, either by HPLC or by formation of diastereoisomeric lactanilide derivatives. For the first time, the rates of Ar-N rotation in 2-substituted N,N-diarylureas have been established: they mainly fall in the region of 50-70 kJ mol-1 with a relatively weak dependence on substituent size. {\textcopyright} The Royal Society of Chemistry 2005.",

author = "Thomas Adler and Josep Bonjoch and Jonathan Clayden and Merc{\`e} Font-Bard{\'i}a and Mark Pickworth and Xavier Solans and Daniel Sol{\'e} and Llu{\'i}s Vallverd{\'u}",

year = "2005",

month = sep,

day = "7",

doi = "10.1039/b507202f",

language = "English",

volume = "3",

pages = "3173--3183",

journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

AU - Adler, Thomas

AU - Bonjoch, Josep

AU - Clayden, Jonathan

AU - Font-Bardía, Mercè

AU - Pickworth, Mark

AU - Solans, Xavier

AU - Solé, Daniel

AU - Vallverdú, Lluís

PY - 2005/9/7

Y1 - 2005/9/7

N2 - N-Acylated 2-substituted anilines undergo slow Ar-N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar-N bond rotation by NMR. 2-Iodoanilides bearing a branched N-substituent demonstrate sufficient enantiomeric stability to be resolvable, either by HPLC or by formation of diastereoisomeric lactanilide derivatives. For the first time, the rates of Ar-N rotation in 2-substituted N,N-diarylureas have been established: they mainly fall in the region of 50-70 kJ mol-1 with a relatively weak dependence on substituent size. © The Royal Society of Chemistry 2005.

AB - N-Acylated 2-substituted anilines undergo slow Ar-N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar-N bond rotation by NMR. 2-Iodoanilides bearing a branched N-substituent demonstrate sufficient enantiomeric stability to be resolvable, either by HPLC or by formation of diastereoisomeric lactanilide derivatives. For the first time, the rates of Ar-N rotation in 2-substituted N,N-diarylureas have been established: they mainly fall in the region of 50-70 kJ mol-1 with a relatively weak dependence on substituent size. © The Royal Society of Chemistry 2005.

U2 - 10.1039/b507202f

DO - 10.1039/b507202f

M3 - Article

SN - 1477-0520

VL - 3

SP - 3173

EP - 3183

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines

Abstract

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Datasets

CCDC 273163: Experimental Crystal Structure Determination

Cite this