47301-29-1Relevant articles and documents
A novel type of hydrogen-bonded assemblies based on the melamine·cyanuric acid motif
Arduini, Maria,Crego-Calama, Mercedes,Timmerman, Peter,Reinhoudt, David N.
, p. 1097 - 1106 (2003)
This paper reports the formation of novel hydrogen-bonded assemblies 13·CA obtained upon mixing cyanuric acid (CA) with melamine derivatives 1, in which two of the three possible H-bonding arrays have been blocked. The four components are held together by 9 hydrogen bonds and form a rigid planar structure in which a central CA (three ADA motifs: A = acceptor, D = donor) is hydrogen bonded to three peripheral melamine derivatives (DAD motif). Furthermore, the synthesis and assembly studies are described of hydrogen-bonded assemblies 2-4·CA, comprised of three melamine derivatives that are covalently connected, and CA. The overall thermodynamic stability of assemblies 2-4·CA is superior to 13·CA (ITm = 9 vs 3.6). The presence of the 2·CA complex in chloroform was confirmed by 1H NMR spectroscopy and MALDI-TOF mass spectrometry. Substitution of the trimelamines with chiral or fluorescent groups (R3) enabled the study of the assemblies by CD and fluorescence spectroscopy. Titration experiments revealed strongly enhanced stabilities even in the presence of polar solvents, such as THF and CH3OH. Depending on the polarity of the solvent, stacking between the planar assembly units was observed.
Hindered C–N bond rotation in triazinyl dithiocarbamates
Jung, Taesub,Do, Hee-Jin,Son, Jongwoo,Song, Jae Hee,Cha, Wansik,Kim, Yeong-Joon,Lee, Kyung-Koo,Kwak, Kyungwon
, p. 215 - 222 (2017/10/06)
The substituent and solvent effects on the rotation around a C–N amide bond were studied for a series of triazine dibenzylcarbamodithioates. The Gibbs free energies (ΔG?) were measured to be 16–18 kcal/mol in DMSO-d6 and toluene-d8 using variable-temperature nuclear magnetic resonance (VT-1H NMR) spectroscopy. Density functional theory (DFT) calculations reproduced the experimental observations with various substituents, as well as solvents. From the detailed analysis of the DFT results, we found that the electron donating dibenzyl amine group increased the electron population on the triazinyl ring, which decreased the rotational barrier of the C–N bond in the dithiocarbamate group attached to the triazinyl ring. The higher electron population on the triazine moiety stabilizes the partial double bond character of the S–C bond, which competitively excludes the double bond character of the C–N bond. Therefore, the rotational dynamics of the C–N bond in dithiocarbamates can be a sensitive probe to small differences in the electron population of substituents on sulfur.
Self-assembly of a [2 x 2] hydrogen bonded grid
Lipkowski, Piotr,Bielejewska, Anna,Kooijman, Huub,Spek, Anthony L.,Timmerman, Peter,Reinhoudt, David N.
, p. 1311 - 1312 (2007/10/03)
Formation of 24 cooperative hydrogen bonds drives the spontaneous assembly of a rigid bifunctional trimelamine and bis(barbituric acid) to give selectively the [2 x 2] hydrogen-bonded grid, in preference to the corresponding [1 x 1] or polymeric assemblie