Observation of two N2‐isobutyrylguanine tautomers by NMR spectroscopy. (20th November 2012)

• Record Type: Journal Article
• Authors: Yang, Lijing; Li, Jia; Simionescu, Razvan; Yan, Hongbin
• Is Part Of: Magnetic resonance in chemistry. Volume 51:Number 1(2013:Jan.)
• Page Start: 60
• Page End: 64
• Publication Date: 2012-11-20
• Subjects: Nuclear magnetic resonance spectroscopy -- Periodicals; Chemistry, Organic -- Periodicals; Magnetic resonance -- Periodicals; 538.36
• DOI: 10.1002/mrc.3901
• Languages: English
• ISSNs: 0749-1581

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <italic>N</italic> ₂‐Isobutyrylguanine was prepared by treatment of guanine with isobutyryl chloride. Two tautomers, 1, 7‐dihydro‐2‐(isobutyroyl)amino‐6<italic>H</italic>‐purin‐6‐one and 1, 9‐dihydro‐2‐(isobutyroyl)amino‐6<italic>H</italic>‐purin‐6‐one, were identified in almost 1 : 1 ratio in dichloromethane–dimethyl sulfoxide (1 : 1 v/v) by NMR spectroscopy. By using the selective‐inversion experiments, enthalpy, entropy, and free energy for activation were determined. This work represents the first report of guanine tautomers observed directly by NMR spectroscopy. Copyright © 2012 John Wiley &amp; Sons, Ltd.</p> </abstract>