Aminolysis of Y-Substituted Phenyl X-Substituted Benzoates with Piperidine: Effect of Nonleaving Group Substituent
The Journal of Organic Chemistry2006Vol. 71(15), pp. 5800–5803
Citations Over TimeTop 10% of 2006 papers
Abstract
The title reaction has been suggested to proceed through a zwitterionic tetrahedral intermediate with a change in the rate determining step on the basis of the curved Brønsted-type plots obtained. The curvature center of the curved Brønsted-type plots is at pKa = 6.4 regardless of the electronic nature of the substituent X in the benzoyl moiety.
Related Papers
- → Potent pyrimidinetrione-based inhibitors of MMP-13 with enhanced selectivity over MMP-14(2005)59 cited
- → Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: influence on topoisomerase I-targeting activity and cytotoxicity(2004)34 cited
- → Substituent-Modulated Conformation and Supramolecular Assembly of Tetronamides(2016)7 cited
- The Effect of Acyl Substituent on the α-Effect in the Aminolysis of p-Nitrophenyl X-Substituted Benzoates(2018)
- → ChemInform Abstract: The Triphenylmethyl Group — A Kinetically Stabilizing Substituent and Protecting Group in Organophosphorus Chemistry(2000)