Influence of neighboring phenyl participation on the $alpha$-deuterium isotope effect on solvolysis rates. Neophyl esters

Journal Article · Sat Jan 31 23:00:00 EST 1976 · J. Am. Chem. Soc., v. 98, no. 3, pp. 862-864

DOI:https://doi.org/10.1021/ja00419a051· OSTI ID:4052661

Shiner, Jr, V J; Seib, R C

The isotope effects of deuterium on substituted neophyl ester solvolysis rates were studied to determine the influence of phenyl participation on isotope effects, and to determine the relationship of transition state structure to solvent, substituent, and leaving group. The $alpha$-d isotope effects and the solvolysis rates for the acetolysis and trifluoroacetolysis of several neophyl esters were tabulated. It was determined that the isotope effects were lower in reactions where the phenyl ring participated in the rate determining ionization than in reactions where participation was absent. (DDA)

• Research Organization: Indiana Univ., Bloomington
• Sponsoring Organization: USDOE
• NSA Number: NSA-33-028486
• OSTI ID: 4052661
• Journal Information: J. Am. Chem. Soc., v. 98, no. 3, pp. 862-864, Journal Name: J. Am. Chem. Soc., v. 98, no. 3, pp. 862-864; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

*DEUTERIUM-- ISOTOPE EFFECTS
*ESTERS-- SOLVOLYSIS
400302* --Chemistry--Organic Chemistry--Isotope Effects
ACETIC ACID
ACETOLYSIS
AROMATICS
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
ETHANOL
N40220* --Chemistry--Inorganic
Organic
& Physical Chemistry--Isotopic Effects
ORGANIC BROMINE COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
SPECTROPHOTOMETRY
SULFONIC ACID ESTERS