A mechanistic study of thioester hydrolysis with heavy atom kinetic isotope effects.
J Org Chem
; 80(3): 1905-8, 2015 Feb 06.
Article
in En
| MEDLINE
| ID: mdl-25545007
ABSTRACT
The carbonyl-C, carbonyl-O, and leaving-S kinetic isotope effects (KIEs) were determined for the hydrolysis of formylthiocholine. Under acidic conditions, (13)k(obs) = 1.0312, (18)k(obs) = 0.997, and (34)k(obs) = 0.995; for neutral conditions, (13)k(obs) = 1.022, (18)k(obs) = 1.010, and (34)k(obs) = 0.996; and for alkaline conditions, (13)k(obs) = 1.0263, (18)k(obs) = 0.992, and (34)k(obs) = 1.000. The observed KIEs provided helpful insights into a qualitative description of the bond orders in the transition state structure.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Sulfur Compounds
/
Thiocholine
/
Isotopes
Type of study:
Qualitative_research
Language:
En
Journal:
J Org Chem
Year:
2015
Document type:
Article
Affiliation country:
United States