Dimer self-association via hydrogen bonding: Measurement and comparison of binding constants with 2-amidopyrimidine derivatives

Autor:	K. Wade Elliott, Jeffrey N. Woodford, Emily Byrd, Victor Bednar
Rok vydání:	2012
Předmět:	Chloroform Hydrogen bond Stereochemistry Dimer General Physics and Astronomy Crystallography chemistry.chemical_compound chemistry Proton NMR Peptide bond Density functional theory Physical and Theoretical Chemistry Constant (mathematics) Equilibrium constant
Zdroj:	Chemical Physics Letters. 547:24-29
ISSN:	0009-2614
Popis:	A method based on 1H NMR was used to measure the self-assembly equilibrium constants for three acylated derivatives of 2-aminopyrimidine: 2-acetamidopyrimidine (1), 2-isopropylamidopyrimidine (2), and 2-neopentylamidopyrimidine (3). The synthesis of the latter two compounds is described. The self-association constant decreases from 1 to 2 to 3, which is attributed to the syn/anti conformational preference of the amide bond. For 1, complexation with chloroform must be included in order to explain the observed chemical shift values. Complementary density functional theory calculations (MP2/cc-pVTZ//B3LYP-D/cc-pVDZ) suggest a direct relationship between conformational preference of the amide bond and the self-assembly constant.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bcac757a6da7c812b9d65c2076219ba3 https://doi.org/10.1016/j.cplett.2012.07.044 Zobrazit plný text záznamu Full Text from ScienceDirect