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Water‐Assisted Alkaline Hydrolysis of Monobactams: A Theoretical Study
Author(s) -
Díaz Natalia,
Suárez Dimas,
Sordo Tomás L.,
Tuñón Iñaki,
Silla Estanislao
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020215)8:4<859::aid-chem859>3.0.co;2-i
Subject(s) - hydrolysis , solvation , alkaline hydrolysis , chemistry , solvent , sulfonate , substituent , ring (chemistry) , molecule , computational chemistry , stereochemistry , organic chemistry , sodium
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 β ‐lactam ring are crucial factors determining the hydrolysis of monobactam antibiotics.