title: Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.
abstract: In contrast to observations with carbohydrates, experiments with 4-alkoxy-substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by up to 20-fold compared to substrates without an alkoxy group. The acceleration of ionization in more flexible acetals can be up to 200-fold when compensated for inductive effects.
authors.affiliation: Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA).
authors.forename: Angie
authors.initials: A
authors.lastname: Garcia
authors.forename: Douglas A L
authors.initials: DA
authors.lastname: Otte
authors.forename: Walter A
authors.initials: WA
authors.lastname: Salamant
authors.forename: Jillian R
authors.initials: JR
authors.lastname: Sanzone
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000838:Anions / Q000737:chemistry*; D006868:Hydrolysis; D055672:Static Electricity
chemical_list: D000080:Acetals; D000838:Anions
keywords: carbocations; carbohydrates; electrostatic effects; hydrolysis; kinetics