Revisiting the spectroscopy of xanthine derivatives: theobromine and theophylline

被引：9

作者：

Camiruaga, Ander ^{[1
]}

Usabiaga, Imanol ^{[1
]}

D'mello, Viola C. ^{[2
]}

Garcia, Gustavo A. ^{[3
]}

Wategaonkar, Sanjay ^{[2
]}

Fernandez, Jose A. ^{[1
]}

机构：

[1] Univ Basque Country, Fac Sci & Technol, Dep Phys Chem, UPV EHU, Barrio Sarriena S-N, Leioa 48940, Spain

[2] Tata Inst Fundamental Res, Dept Chem Sci, Mumbai 400005, Maharashtra, India

[3] Synchrotron SOLEIL, St Aubin BP 48, F-91192 Gif Sur Yvette, France

来源：

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | 2019年 / 21卷 / 48期

关键词：

PHOTOELECTRON-SPECTROSCOPY; DENSITY FUNCTIONALS; ELECTRONIC-SPECTRA; EXCITED-STATES; BASIS-SETS; GAS-PHASE; AB-INITIO; ADENINE; DYNAMICS; NUCLEOBASES;

D O I：

10.1039/c9cp05068j

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We explore the influence of the relative position of the methyl substituent on the photophysics of theophylline and theobromine, two molecules that are structurally related to the DNA bases. Using a combination of spectroscopic techniques and quantum mechanical calculations, we show that moving the methyl group from N1 in theophylline to N7 in theobromine causes significant differences in their excited state properties, i.e., it produces pyramidalization of N7 in the excited state of the latter. Paradoxically, this modification seems to have little effect on the structural properties of the cation and the ionization process. It is suggested that similar effects may exist in the excited state properties of DNA bases.

引用

页码：26430 / 26437

页数：8

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