On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding

Dana Marcovici-Mizrahi; Hugo E. Gottlieb; Vered Marks; Abraham Nudelman

doi:10.1021/jo961446u

On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding

Dana Marcovici-Mizrahi, Hugo E. Gottlieb, Vered Marks, Abraham Nudelman

Department of Chemistry

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Abstract

The syn-rotamers of carbamate derivatives of α-amino acids are shown to be stabilized by the formation of H-bond complexes with carboxylic acid moieties in solution. This effect is, as expected, concentration and temperature dependent. Thermodynamic parameters (both ΔG° and ΔG‡) for N-Boc-alanine were determined by NMR in the ±60 °C range.

Original language	English
Pages (from-to)	8402-8406
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	61
Issue number	24
DOIs	https://doi.org/10.1021/jo961446u
State	Published - 29 Nov 1996

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abstract = "The syn-rotamers of carbamate derivatives of α-amino acids are shown to be stabilized by the formation of H-bond complexes with carboxylic acid moieties in solution. This effect is, as expected, concentration and temperature dependent. Thermodynamic parameters (both ΔG° and ΔG‡) for N-Boc-alanine were determined by NMR in the ±60 °C range.",

author = "Dana Marcovici-Mizrahi and Gottlieb, {Hugo E.} and Vered Marks and Abraham Nudelman",

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AU - Marcovici-Mizrahi, Dana

AU - Gottlieb, Hugo E.

AU - Marks, Vered

AU - Nudelman, Abraham

PY - 1996/11/29

Y1 - 1996/11/29

N2 - The syn-rotamers of carbamate derivatives of α-amino acids are shown to be stabilized by the formation of H-bond complexes with carboxylic acid moieties in solution. This effect is, as expected, concentration and temperature dependent. Thermodynamic parameters (both ΔG° and ΔG‡) for N-Boc-alanine were determined by NMR in the ±60 °C range.

AB - The syn-rotamers of carbamate derivatives of α-amino acids are shown to be stabilized by the formation of H-bond complexes with carboxylic acid moieties in solution. This effect is, as expected, concentration and temperature dependent. Thermodynamic parameters (both ΔG° and ΔG‡) for N-Boc-alanine were determined by NMR in the ±60 °C range.

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On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding

Abstract

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