Conformational evaluation of indol-3-yl-N-alkyl-glyoxalylamides and indol-3-yl-N, N-dialkyl-glyoxalylamides

David Mansell; Simon D. Brandt; Sabiya Nasima; Nicola Turvey; John F. Alder; Sally Freeman; Carl H. Schwalbe

doi:10.1080/00387010902772336

Conformational evaluation of indol-3-yl-N-alkyl-glyoxalylamides and indol-3-yl-N, N-dialkyl-glyoxalylamides

David Mansell, Simon D. Brandt, Sabiya Nasima, Nicola Turvey, John F. Alder, Sally Freeman, Carl H. Schwalbe

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

Abstract

Restricted rotation in indol-3-yl-N-alkyl- and indol-3-yl-N,N-dialkyl-glyoxalylamides can in principle give the syn-periplanar and anti-periplanar rotamers. In asymmetrically disubstituted glyoxalylamides, steric effects lead to the occurrence of both rotamers, as observed by NMR spectroscopy. The predominant peak corresponds with the anti rotamer, in which the bulkier alkyl group is orientated trans to the amide carbonyl group. In monoalkylated glyoxalylamides, only one set of peaks is observed, consistent with the presence of only one rotamer. Crystal structures of 5-methoxyindole-3-yl-N-tert-butylglyoxalylamide, indole-3-yl-N-tert-butylglyoxalylamide, and indole-3-yl-N-isopropylglyoxalylamide reported here reveal a syn conformation held by an intramolecular N-H...O hydrogen bond. © Taylor & Francis Group, LLC.

Original language	English
Pages (from-to)	156-166
Number of pages	10
Journal	Spectroscopy Letters
Volume	42
Issue number	3
DOIs	https://doi.org/10.1080/00387010902772336
Publication status	Published - Apr 2009

Keywords

Amides
Crystal structure
Glyoxalylamides
Indole
Intramolecular hydrogen bond
Nuclear magnetic resonance
Rotamers

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10.1080/00387010902772336

CCDC 670830: Experimental Crystal Structure Determination
Mansell, D. (Contributor), Brandt, S. D. (Contributor), Nasima, S. (Contributor), Turvey, N. (Contributor), Alder, J. F. (Contributor), Freeman, S. (Contributor) & Schwalbe, C. H. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccqj1py, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqj1py&sid=DataCite
Dataset
CCDC 670832: Experimental Crystal Structure Determination
Mansell, D. (Contributor), Brandt, S. D. (Contributor), Nasima, S. (Contributor), Turvey, N. (Contributor), Alder, J. F. (Contributor), Freeman, S. (Contributor) & Schwalbe, C. H. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccqj1r0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqj1r0&sid=DataCite
Dataset
CCDC 670831: Experimental Crystal Structure Determination
Mansell, D. (Contributor), Brandt, S. D. (Contributor), Nasima, S. (Contributor), Turvey, N. (Contributor), Alder, J. F. (Contributor), Freeman, S. (Contributor) & Schwalbe, C. H. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccqj1qz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqj1qz&sid=DataCite
Dataset

Cite this

@article{e83068f0f5c943998a84ede5f27baa3b,

title = "Conformational evaluation of indol-3-yl-N-alkyl-glyoxalylamides and indol-3-yl-N, N-dialkyl-glyoxalylamides",

abstract = "Restricted rotation in indol-3-yl-N-alkyl- and indol-3-yl-N,N-dialkyl-glyoxalylamides can in principle give the syn-periplanar and anti-periplanar rotamers. In asymmetrically disubstituted glyoxalylamides, steric effects lead to the occurrence of both rotamers, as observed by NMR spectroscopy. The predominant peak corresponds with the anti rotamer, in which the bulkier alkyl group is orientated trans to the amide carbonyl group. In monoalkylated glyoxalylamides, only one set of peaks is observed, consistent with the presence of only one rotamer. Crystal structures of 5-methoxyindole-3-yl-N-tert-butylglyoxalylamide, indole-3-yl-N-tert-butylglyoxalylamide, and indole-3-yl-N-isopropylglyoxalylamide reported here reveal a syn conformation held by an intramolecular N-H...O hydrogen bond. {\textcopyright} Taylor & Francis Group, LLC.",

keywords = "Amides, Crystal structure, Glyoxalylamides, Indole, Intramolecular hydrogen bond, Nuclear magnetic resonance, Rotamers",

author = "David Mansell and Brandt, {Simon D.} and Sabiya Nasima and Nicola Turvey and Alder, {John F.} and Sally Freeman and Schwalbe, {Carl H.}",

year = "2009",

month = apr,

doi = "10.1080/00387010902772336",

language = "English",

volume = "42",

pages = "156--166",

journal = "Spectroscopy Letters",

issn = "0038-7010",

publisher = "Taylor & Francis",

number = "3",

}

TY - JOUR

T1 - Conformational evaluation of indol-3-yl-N-alkyl-glyoxalylamides and indol-3-yl-N, N-dialkyl-glyoxalylamides

AU - Mansell, David

AU - Brandt, Simon D.

AU - Nasima, Sabiya

AU - Turvey, Nicola

AU - Alder, John F.

AU - Freeman, Sally

AU - Schwalbe, Carl H.

PY - 2009/4

Y1 - 2009/4

N2 - Restricted rotation in indol-3-yl-N-alkyl- and indol-3-yl-N,N-dialkyl-glyoxalylamides can in principle give the syn-periplanar and anti-periplanar rotamers. In asymmetrically disubstituted glyoxalylamides, steric effects lead to the occurrence of both rotamers, as observed by NMR spectroscopy. The predominant peak corresponds with the anti rotamer, in which the bulkier alkyl group is orientated trans to the amide carbonyl group. In monoalkylated glyoxalylamides, only one set of peaks is observed, consistent with the presence of only one rotamer. Crystal structures of 5-methoxyindole-3-yl-N-tert-butylglyoxalylamide, indole-3-yl-N-tert-butylglyoxalylamide, and indole-3-yl-N-isopropylglyoxalylamide reported here reveal a syn conformation held by an intramolecular N-H...O hydrogen bond. © Taylor & Francis Group, LLC.

AB - Restricted rotation in indol-3-yl-N-alkyl- and indol-3-yl-N,N-dialkyl-glyoxalylamides can in principle give the syn-periplanar and anti-periplanar rotamers. In asymmetrically disubstituted glyoxalylamides, steric effects lead to the occurrence of both rotamers, as observed by NMR spectroscopy. The predominant peak corresponds with the anti rotamer, in which the bulkier alkyl group is orientated trans to the amide carbonyl group. In monoalkylated glyoxalylamides, only one set of peaks is observed, consistent with the presence of only one rotamer. Crystal structures of 5-methoxyindole-3-yl-N-tert-butylglyoxalylamide, indole-3-yl-N-tert-butylglyoxalylamide, and indole-3-yl-N-isopropylglyoxalylamide reported here reveal a syn conformation held by an intramolecular N-H...O hydrogen bond. © Taylor & Francis Group, LLC.

KW - Amides

KW - Crystal structure

KW - Glyoxalylamides

KW - Indole

KW - Intramolecular hydrogen bond

KW - Nuclear magnetic resonance

KW - Rotamers

U2 - 10.1080/00387010902772336

DO - 10.1080/00387010902772336

M3 - Article

SN - 0038-7010

VL - 42

SP - 156

EP - 166

JO - Spectroscopy Letters

JF - Spectroscopy Letters

IS - 3

ER -

Conformational evaluation of indol-3-yl-N-alkyl-glyoxalylamides and indol-3-yl-N, N-dialkyl-glyoxalylamides

Abstract

Keywords

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Datasets

CCDC 670830: Experimental Crystal Structure Determination

CCDC 670832: Experimental Crystal Structure Determination

CCDC 670831: Experimental Crystal Structure Determination

Cite this