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

Autor(es)

Cormanich, Rodrigo A. ^[1] ; Buehl, Michael ^[2] ; Rittner, Roberto ^[1]

Afiliação do(s) autor(es)

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

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

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 13, n. 35, p. 9206-9213, 2015.
• Citações Web of Science: 9

Resumo

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)

• Processo FAPESP: 11/01170-1 - Estudos físico-químicos de compostos orgânicos: interações de longa distância e análise conformacional de compostos organofluorados
• Beneficiário: Rodrigo Antonio Cormanich
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 14/25903-6 - Estudos de estrutura molecular de alguns aminoácidos e dipeptídios
• Beneficiário: Roberto Rittner Neto
• Modalidade de apoio: Auxílio à Pesquisa - Regular