Water-Assisted Alkaline Hydrolysis of Monobactams: A Theoretical Study

6533b7d3fe1ef96bd1260966

RESEARCH PRODUCT

Water-Assisted Alkaline Hydrolysis of Monobactams: A Theoretical Study

Estanislao Silla Natalia Díaz Dimas Suárez Tomás L. Sordo Iñaki Tuñón

subject

Molecular Structure Hydrolysis Organic Chemistry Inorganic chemistry Substituent Water General Chemistry Catalysis Ion Solvent Structure-Activity Relationship Hydrolysis chemistry.chemical_compound Models Chemical chemistry Hydroxides Solvents Azetidines Thermodynamics Molecule Solvent effects Monobactams Alkaline hydrolysis Monobactams

description

A theoretical study of the water-assisted alkaline hydrolysis of 2-azetidinone, 3-formylamino-2-azetidinone and 3-formylamino-2-azetidine-1-sulfonate ion is carried out at the B3LYP/6-31+G* level. The effect of bulk solvent is taken into account using the PCM solvation model while specific solvent effects are represented by the inclusion of an ancillary water molecule along the reaction profile. The calculated free energy barriers in solution are in reasonable agreement with experimental values. The observed substituent effects due to the presence of the 3-formylamino and the SO(3) groups attached to the beta-lactam ring are crucial factors determining the hydrolysis of monobactam antibiotics.

year	journal	country	edition	language
2002-02-15	Chemistry - A European Journal

https://doi.org/10.1002/1521-3765(20020215)8:4<859::aid-chem859>3.0.co;2-i

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