Conformational preferences of Ac-Gly-NHMe in solution

Author(s)

Cormanich, R. A. ^{[1, 2]} ; Rittner, R. ^[1] ; Buehl, M. ^[2]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Univ St Andrews, EastChem Sch Chem, St Andrews KY16 9ST, Fife - Scotland

• Document type: Journal article
• Source: RSC ADVANCES; v. 5, n. 17, p. 13052-13060, 2015.
• Web of Science Citations: 7

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 H-1 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. (AU)

• FAPESP's process: 11/01170-1 - Physicochemical studies of organic compounds: long range inractions and conformational analysis of organofluorine compounds.
• Grantee: Rodrigo Antonio Cormanich
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/03933-5 - Conformational equilibria and intramolecular interactions for a series of amino-acids: theoretical and experimental approaches
• Grantee: Roberto Rittner Neto
• Support Opportunities: Regular Research Grants