A consideration of the barrier for carbocation-nucleophile combination reactions.

J. P. Richard, Tetrahedron, 1995, 51, 1535.

Key Words:
LASER FLASH-PHOTOLYSIS/SUBSTITUTED 1-PHENYL-2,2,2-TRIFLUOROETHYL CARBOCATIONS/REACTIVITY-SELECTIVITY RELATIONSHIP/ELECTRONIC GEMINAL INTERACTIONS/NITRENIUM ION CHARACTER/GENERAL BASE CATALYSIS/SIMPLE QUINONE METHIDE/CN RATE RATIOS/H-ALPHA-CN/SOLVOLYSIS REACTIONS



How does structure determine organic reactivity? Partitioning of carbocations between addition of nucleophiles and deprotonation.

J. P. Richard, T. L. Amyes, S. S. Lin, A. C. ODonoghue, M. M. Toteva, Y. Tsuji, K. B. Williams, Adv. Phys. Org. Chem., 2000, 35, 67.

Key Words:
VINYL ETHER HYDROLYSIS/ACID-CATALYZED HYDROLYSIS/SOLVOLYTIC ELIMINATION-REACTIONS/SUBSTITUTED 4-METHOXYBENZYL CARBOCATIONS/REVERSIBLE CARBON PROTONATION/LASER FLASH-PHOTOLYSIS/GENERAL BASE CATALYSIS/RATE-DETERMINING STEP/AQUEOUS-SOLUTION/REACTION-MECHANISM



Formation and stability of carbocations and carbanions in water and intrinsic barriers to their reactions.

J. P. Richard, T. L. Amyes, M. M. Toteva, Acc. Chem. Res., 2001, 34, 981.

Key Words:
SUBSTITUTED 1-PHENYLETHYL CARBOCATIONS/STRUCTURE-REACTIVITY RELATIONSHIPS/SIMPLE QUINONE METHIDE/AQUEOUS-SOLUTION/4-METHOXYBENZYL CARBOCATIONS/THERMODYNAMIC STABILITY/NUCLEOPHILIC-REAGENTS/ALPHA-SUBSTITUENTS/FLASH-PHOTOLYSIS/GENERATION



Intrinsic barriers to the formation and reaction of carbocations.

J. P. Richard, T. L. Amyes, K. B. Williams, Pure Appl. Chem., 1998, 70, 2007.

Key Words:
VINYL ETHER HYDROLYSIS/4-METHOXYBENZYL CARBOCATIONS/ALPHA-SUBSTITUENTS/PROTON-TRANSFER/CARBON ACIDS/SYNCHRONIZATION/STABILITY/PRINCIPLE