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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Cormanich, Rodrigo A. [1] ; Buehl, Michael [2] ; Rittner, Roberto [1]
Total Authors: 3
[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
[2] Univ St Andrews, EastChem Sch Chem, St Andrews KY16 9ST, Fife - Scotland
Total Affiliations: 2
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 13, n. 35, p. 9206-9213, 2015.
Web of Science Citations: 9

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 H-1 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. (AU)

FAPESP's process: 14/25903-6 - Molecular structure of some amino acids and dipeptides
Grantee:Roberto Rittner Neto
Support type: Regular Research Grants
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 type: Scholarships in Brazil - Doctorate