Acceleration of acetal hydrolysis by remote alkoxy groups: Evidence for electrostatic effects on the formation of oxocarbenium ions

Angie Garcia; Douglas A.L. Otte; Walter A. Salamant; Jillian R. Sanzone; K. A. Woerpel

doi:10.1002/anie.201410043

Acceleration of acetal hydrolysis by remote alkoxy groups: Evidence for electrostatic effects on the formation of oxocarbenium ions

Angie Garcia, Douglas A.L. Otte, Walter A. Salamant, Jillian R. Sanzone, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	3061-3064
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	10
DOIs	https://doi.org/10.1002/anie.201410043
State	Published - Mar 2 2015

Keywords

Carbocations
Carbohydrates
Electrostatic effects
Hydrolysis
Kinetics

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201410043

Cite this

@article{d45b158615d74ce38fa5548aa1bffb63,

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.",

keywords = "Carbocations, Carbohydrates, Electrostatic effects, Hydrolysis, Kinetics",

author = "Angie Garcia and Otte, {Douglas A.L.} and Salamant, {Walter A.} and Sanzone, {Jillian R.} and Woerpel, {K. A.}",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2015",

month = mar,

day = "2",

doi = "10.1002/anie.201410043",

language = "English (US)",

volume = "54",

pages = "3061--3064",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "10",

}

TY - JOUR

T1 - Acceleration of acetal hydrolysis by remote alkoxy groups

T2 - Evidence for electrostatic effects on the formation of oxocarbenium ions

AU - Garcia, Angie

AU - Otte, Douglas A.L.

AU - Salamant, Walter A.

AU - Sanzone, Jillian R.

AU - Woerpel, K. A.

PY - 2015/3/2

Y1 - 2015/3/2

N2 - 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.

AB - 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.

KW - Carbocations

KW - Carbohydrates

KW - Electrostatic effects

KW - Hydrolysis

KW - Kinetics

UR - http://www.scopus.com/inward/record.url?scp=84923368406&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84923368406&partnerID=8YFLogxK

U2 - 10.1002/anie.201410043

DO - 10.1002/anie.201410043

M3 - Article

C2 - 25614209

AN - SCOPUS:84923368406

SN - 1433-7851

VL - 54

SP - 3061

EP - 3064

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

Acceleration of acetal hydrolysis by remote alkoxy groups: Evidence for electrostatic effects on the formation of oxocarbenium ions

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this