35558-36-2

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 3768-56-7 1-(trimethylsilyl)piperidine 
• 110-89-4 piperidine 
• 7471-13-8 N-(pyrid-2-ylmethylene)-p-tolylamine 
• 100-01-6 4-nitro-aniline 
• 106-49-0 p-toluidine 
• 591-19-5 m-Bromoaniline 
• 2237-30-1 m-cyanoaniline 
• 29202-20-8 N-m-methoxyphenylpicolinaldimine 
• 373647-96-2 [(4-trifluoromethylphenyl)imino methyl]pyridine 
• 67912-40-7 2-<(4-nitrophenyl)iminomethyl>pyridine 
• 400756-02-7 C₁₃H₉N₃ 
• 7032-25-9 2-(phenyliminomethyl)pyridine 
• 26930-67-6 N-(pyrid-2-ylmethylene)-p-methoxyphenylamine 

Downstream Products

• 122713-65-9 piperidino-3 phenyl-2 (pyridyl-2)-3 propionate de methyle 
• 1121-60-4 pyridine-2-carbaldehyde 

Relevant academic research and scientific papers

Quantitative Reactivity Scales for Dynamic Covalent and Systems Chemistry

Dynamic covalent chemistry (DCC) has become a powerful tool for the creation of molecular assemblies and complex systems in chemistry and materials science. Herein we developed for the first time quantitative reactivity scales capable of correlation and prediction of the equilibrium of dynamic covalent reactions (DCRs). The reference reactions are based upon universal DCRs between imines, one of the most utilized structural motifs in DCC, and a series of O-, N-, and S- mononucleophiles. Aromatic imines derived from pyridine-2-carboxyaldehyde exhibit capability for controlling the equilibrium through distinct substituent effects. Electron-donating groups (EDGs) stabilize the imine through quinoidal resonance, while electron-withdrawing groups (EWGs) stabilize the adduct by enhancing intramolecular hydrogen bonding, resulting in curvature in Hammett analysis. Notably, unique nonlinearity induced by both EDGs and EWGs emerged in Hammett plot when cyclic secondary amines were used. This is the first time such a behavior is observed in a thermodynamically controlled system, to the best of our knowledge. Unified quantitative reactivity scales were proposed for DCC and defined by the correlation log K = SN (RN + RE). Nucleophilicity parameters (RN and SN) and electrophilicity parameters (RE) were then developed from DCRs discovered. Furthermore, the predictive power of those parameters was verified by successful correlation of other DCRs, validating our reactivity scales as a general and useful tool for the evaluation and modeling of DCRs. The reactivity parameters proposed here should be complementary to well-established kinetics based parameters and find applications in many aspects, such as DCR discovery, bioconjugation, and catalysis.

Trimethylsilylamines III: mise en evidence du compose d'addition sur les aldehydes; preparation d'aminals et de β-dialkylamino β-arylesters en milieu aprotique

Dialkylaminotrimethylsilanes react with aromatic aldehydes using trimethylsilyltriflate and tetrabutylammonium fluoride as catalysts and lead quantitatively to the corresponding aminals in aprotic media.The intermediate silylated hemiaminal can be characterized in many cases, mainly with pyridinecarbaldehydes.Aminals are obtained from aliphatic aldehydes using fluoride ion as catalyst.A one-pot synthesis of some β-dialkylamino β-arylesters from these reagents is described.