Conformational preferences of Ac-Gly-NHMe in solution

Rodrigo Antonio Cormanich; Roberto  Rittner; Michael Buehl

doi:10.1039/C4RA16472E

Conformational preferences of Ac-Gly-NHMe in solution

Rodrigo Antonio Cormanich, Roberto Rittner, Michael Buehl

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

Abstract

The conformational behaviour of Ac-Gly-NHMe in nonpolar, polar and polar protic solutions was systematically studied in this work by theoretical calculations and experimental infrared and ¹H NMR spectroscopies. Ac-Gly-NHMe prefers a gauche conformer with a strong seven-membered intramolecular hydrogen bond for the isolated compound and in nonpolar solvents, but such preference changes in polar and polar protic solvents. Elucidation of Ac-Gly-NHMe preferences was also supported by studying the conformers of its CF₃-C(O)-Gly-NHMe and Ac-Gly-N(Me)₂ derivatives in solution.

Original language	English
Pages (from-to)	13052-13060
Journal	RSC Advances
Volume	5
Issue number	16
Early online date	13 Jan 2015
DOIs	https://doi.org/10.1039/C4RA16472E
Publication status	Published - 2015

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10.1039/C4RA16472E

pubRodrigo-AcGlyNHMe-revised
© Royal Society of Chemistry 2015. No further copies may be made or distributed. 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 http://dx.doi.org/10.1039/C4RA16472E
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title = "Conformational preferences of Ac-Gly-NHMe in solution",

abstract = "The conformational behaviour of Ac-Gly-NHMe in nonpolar, polar and polar protic solutions was systematically studied in this work by theoretical calculations and experimental infrared and 1H NMR spectroscopies. Ac-Gly-NHMe prefers a gauche conformer with a strong seven-membered intramolecular hydrogen bond for the isolated compound and in nonpolar solvents, but such preference changes in polar and polar protic solvents. Elucidation of Ac-Gly-NHMe preferences was also supported by studying the conformers of its CF3-C(O)-Gly-NHMe and Ac-Gly-N(Me)2 derivatives in solution.",

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

note = "The authors thank a Grant # 2012/03933-5, S{\~a}o Paulo Research Foundation (FAPESP) for providing financial support for this research and a scholarship to RAC #2011/01170-1 (FAPESP). CNPq is also acknowledged, such as for fellowships (to RR) and a studentship (to RAC). ",

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language = "English",

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T1 - Conformational preferences of Ac-Gly-NHMe in solution

AU - Cormanich, Rodrigo Antonio

AU - Rittner, Roberto

AU - Buehl, Michael

N1 - The authors thank a Grant # 2012/03933-5, São Paulo Research Foundation (FAPESP) for providing financial support for this research and a scholarship to RAC #2011/01170-1 (FAPESP). CNPq is also acknowledged, such as for fellowships (to RR) and a studentship (to RAC).

PY - 2015

Y1 - 2015

N2 - The conformational behaviour of Ac-Gly-NHMe in nonpolar, polar and polar protic solutions was systematically studied in this work by theoretical calculations and experimental infrared and 1H NMR spectroscopies. Ac-Gly-NHMe prefers a gauche conformer with a strong seven-membered intramolecular hydrogen bond for the isolated compound and in nonpolar solvents, but such preference changes in polar and polar protic solvents. Elucidation of Ac-Gly-NHMe preferences was also supported by studying the conformers of its CF3-C(O)-Gly-NHMe and Ac-Gly-N(Me)2 derivatives in solution.

AB - The conformational behaviour of Ac-Gly-NHMe in nonpolar, polar and polar protic solutions was systematically studied in this work by theoretical calculations and experimental infrared and 1H NMR spectroscopies. Ac-Gly-NHMe prefers a gauche conformer with a strong seven-membered intramolecular hydrogen bond for the isolated compound and in nonpolar solvents, but such preference changes in polar and polar protic solvents. Elucidation of Ac-Gly-NHMe preferences was also supported by studying the conformers of its CF3-C(O)-Gly-NHMe and Ac-Gly-N(Me)2 derivatives in solution.

U2 - 10.1039/C4RA16472E

DO - 10.1039/C4RA16472E

M3 - Article

SN - 2046-2069

VL - 5

SP - 13052

EP - 13060

JO - RSC Advances

JF - RSC Advances

IS - 16

ER -

Conformational preferences of Ac-Gly-NHMe in solution

Abstract

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