Issue 66, 2013
From the journal:

Chemical Communications

Gas-phase infrared spectrum and acidity of the radical cation of 9-methylguanine†

Linda Feketeová,ab   George N. Khairallah,ab   Bun Chan,bc   Vincent Steinmetz,d   Philippe Maître,*d   Leo Radom*bc  and  Richard A. J. O'Hair*ab  

* Corresponding authors

a School of Chemistry, Bio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, Victoria 3010, Australia
E-mail: rohair@unimelb.edu.au

b ARC Centre of Excellence for Free Radical Chemistry and Biotechnology,

c School of Chemistry, The University of Sydney, NSW 2006, Australia

d Laboratoire de Chimie Physique, Université Paris Sud, Orsay, France

Abstract

Oxidative damage to DNA yields guanine radical cations. Their gas-phase IR spectroscopic signature and acidity have been modelled by the radical cation of 9-methylguanine. Comparisons with quantum chemistry calculations suggest that radical cation formation produces the ground-state keto tautomer, which has an N–H acidity enhanced by ∼470 kJ mol−1.

Graphical abstract: Gas-phase infrared spectrum and acidity of the radical cation of 9-methylguanine

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Article information

DOI
https://doi.org/10.1039/C3CC43244K
Article type
Communication
Submitted
02 May 2013
Accepted
03 Jul 2013
First published
15 Jul 2013

Chem. Commun., 2013,49, 7343-7345

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Gas-phase infrared spectrum and acidity of the radical cation of 9-methylguanine

L. Feketeová, G. N. Khairallah, B. Chan, V. Steinmetz, P. Maître, L. Radom and R. A. J. O'Hair, Chem. Commun., 2013, 49, 7343 DOI: 10.1039/C3CC43244K

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