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

Aston Pharmacy School

Research output: Contribution to journal › Article

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-HO hydrogen bond.

Original language	English
Pages (from-to)	156-166
Number of pages	11
Journal	Spectroscopy letters
Volume	42
Issue number	3
Early online date	25 Mar 2009
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

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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-HO hydrogen bond.",

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",

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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-HO hydrogen bond.

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-HO hydrogen bond.

KW - amides

KW - crystal structure

KW - glyoxalylamides

KW - indole

KW - intramolecular hydrogen bond

KW - nuclear magnetic resonance

KW - rotamers

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Conformational Evaluation of Indol-3-yl-N-alkyl-glyoxalylamides and Indol-3-yl-N,N-dialkyl-glyoxalylamides

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