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

Rodrigo Antonio Cormanich; Michael Buehl; Roberto Rittner

doi:10.1039/C5OB01296A

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

Rodrigo Antonio Cormanich, Michael Buehl, Roberto Rittner

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

Abstract

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.

Original language	English
Pages (from-to)	9206-9213
Number of pages	8
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	35
Early online date	21 Jul 2015
DOIs	https://doi.org/10.1039/C5OB01296A
Publication status	Published - 21 Sept 2015

Keywords

Dipeptide models

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10.1039/C5OB01296A

pubRodrigo_AcAlaNHMe_1_
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
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title = "Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study.",

abstract = "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.",

keywords = "Dipeptide models",

author = "Cormanich, {Rodrigo Antonio} and Michael Buehl and Roberto Rittner",

note = "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.). ",

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doi = "10.1039/C5OB01296A",

language = "English",

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T1 - Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study.

AU - Cormanich, Rodrigo Antonio

AU - Buehl, Michael

AU - Rittner, Roberto

N1 - 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.).

PY - 2015/9/21

Y1 - 2015/9/21

N2 - 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.

AB - 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.

KW - Dipeptide models

UR - http://www.rsc.org/suppdata/c5/ob/c5ob01296a/c5ob01296a1.pdf

U2 - 10.1039/C5OB01296A

DO - 10.1039/C5OB01296A

M3 - Article

SN - 1477-0520

VL - 13

SP - 9206

EP - 9213

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 35

ER -

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

Abstract

Keywords

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