Hydrogen Bonding and Stacking π−π Interactions in Solid 6-Thioguanine and 6-Mercaptopurine (Antileukemia and Antineoplastic Drugs) Studied by NMR-NQR Double Resonance Spectroscopy and
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- 作者：J. N. Latosiska ; J. Seliger ; V. agar ; D. V. Burchardt
- 刊名：Journal of Physical Chemistry A
- 出版年：2009
- 出版时间：July 30, 2009
- 年：2009
- 卷：113
- 期：30
- 页码：8781-8790
- 全文大小：367K
- 年卷期：v.113,no.30(July 30, 2009)
- ISSN：1520-5215
文摘
A chemotherapeutic drug 6-thioguanine (2-amino-1,7-dihydro-6H-purine-6-thione, 6-TG) has been studied experimentally in the solid state by NMR-NQR double resonance and theoretically by the density functional theory. Fourteen resonance frequencies on 14N have been detected and assigned to particular nitrogen sites in the 6-TG molecule. A valid assignment of NQR frequencies for 6-mercaptopurine (6-MP) has been proposed. The effects of molecular aggregations, related to intermolecular hydrogen bonding and stacking π−π interactions on the NQR parameters have been analyzed within the DFT and AIM (atoms in molecules) formalism for 6-TG and 6-mercaptopurine (6-MP). The so-called global reactivity descriptors have been calculated to compare the properties of molecules of 6-TG and 6-MP, to check the effect of −NH2 group as well as to identify the differences in crystal packing.