Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study.
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The conformational behaviour of Ac-Ala-NHMe was studied for the compound in the gas-phase and in solution by theoretical calculations and experimental 1H NMR. The conformational preferences of this compound showed to be resultant 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 used in order to simulate the effect of polar protic solvents in disrupting intramolecular hydrogen bonds involving the -NHMe group in Ac-Ala-NHMe.
Cormanich , R A , Buehl , M & Rittner , R 2015 , ' Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study. ' Organic & Biomolecular Chemistry , vol 13 , no. 35 , pp. 9206-9213 . DOI: 10.1039/C5OB01296A
Organic & Biomolecular Chemistry
Copyright 2015 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C5OB01296A
The authors thank EaStCHEM, CNPq and FAPESP for the studentship (to R.A.C. #2011/01170-1, FAPESP), as is CNPq for the fellowship (R.R.).