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Conformation and charge distribution of bicyclic β‐lactams: Structure–activity relationships
Author(s) -
Fernández Berta,
Carballiera Luís,
Ríos Miguel A.
Publication year - 1992
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360320112
Subject(s) - chemistry , heptane , octane , ethylene , bicyclic molecule , ab initio , computational chemistry , derivative (finance) , charge (physics) , charge density , gaussian orbital , stereochemistry , organic chemistry , physics , quantum mechanics , financial economics , economics , catalysis
The structures of 7‐oxo‐1‐azabicyclo[3.2.0] heptane and its 4‐oxa, 3‐ethylene‐4‐oxa, and 3‐ethylene‐6‐methyl‐4‐oxa derivatives, and of 8‐oxo‐1‐azabicyclo[4.2.0] octane and its 5‐oxa derivative, were studied by ab initio methods. Conformations were refined without constraints using the 4‐21G and the 4‐21G* basis sets, and energies and charge distributions were improved by single‐point 6‐31G*/4‐21G* calculations. The results are interpreted in terms of structural trends related to β‐lactamase inhibitor capability.