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Issue 35, 2015
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Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study

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Abstract

The conformational behaviour of Ac-Ala-NHMe was studied in the gas-phase and in solution by theoretical calculations (B3LYP-D3/aug-cc-pVDZ level) and experimental 1H NMR. The conformational preferences of this compound were shown to result from a complex interplay between the strengths of possible intramolecular hydrogen bonds, steric interactions, hyperconjugation, entropy effects and the overall dipole moments. The Ac-Ala-N(Me)2 derivative was studied in addition, to design a system akin to Ac-Ala-NHMe, but with disrupted intramolecular hydrogen bonds involving the -NHMe group, mimicking the effect of polar protic solvents.

Graphical abstract: Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study

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Publication details

The article was received on 25 Jun 2015, accepted on 21 Jul 2015 and first published on 21 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01296A
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Org. Biomol. Chem., 2015,13, 9206-9213

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    Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study

    R. A. Cormanich, M. Bühl and R. Rittner, Org. Biomol. Chem., 2015, 13, 9206
    DOI: 10.1039/C5OB01296A

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