Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.3/235677

Title

Photoelectron spectra of some antibiotic building blocks: 2-azetidinone and thiazolidine-carboxylic acid

Author(s)

Ahmed, Marawan;  Ganesan, Aravindhan;  Wang, Feng;  Feyer, Vitaliy;  Plekan, Oksana;  Prince, Kevin C.

Abstract

X-ray photoelectron spectra of the core and valence levels of the fundamental building blocks of β-lactam antibiotics have been investigated and compared with theoretical calculations. The spectra of the compounds 2-azetidinone and the 2- and 4-isomers of thiazolidinecarboxylic acid are interpreted in the light of theoretical calculations. The spectra of the two isomers of thiazolidinecarboxylic acid are rather similar, as expected, but show clear effects due to isomerization. Both isomers are analogues of proline, which is wellknown\ to populate several low energy conformers in the gas phase. We have investigated the low energy conformers of thiazolidine-4-carboxylic acid theoretically in more detail and find some spectroscopic evidence that multiple conformers may be present. The measured valence levels are assigned for all three compounds, and the character of the frontier orbitals is identified and analyzed.

Publication type

Journal article

Research centre

Swinburne University of Technology. Faculty of Life and Social Sciences

Source

Journal of Physical Chemistry A, Vol. 116, no. 33 (Aug 2012), pp. 8653-8660

Publication year

2012

FOR Code(s)

0202 Atomic, Molecular, Nuclear, Particle and Plasma Physics;  0306 Physical Chemistry (Incl. Structural);  0307 Theoretical and Computational Chemistry

Keyword(s)

2-azetidinone;  Antibiotics;  Isomers;  Photoelectron Spectra;  Thiazolidine-carboxylic acid

Publisher

American Chemical Society

ISSN

1089-5639

Publisher URL

http://dx.doi.org/10.1021/jp302950y

Copyright

Copyright © 2012 American Chemical Society.

Peer reviewed