Lone pair-π vs π-π interactions in 5-fluoro-1-hexyluracil and 1-hexyluracil: a combined crystallographic and computational study

被引:40
作者
Barcelo-Oliver, Miquel [1 ]
Estarellas, Carolina [1 ]
Garcia-Raso, Angel [1 ]
Terron, Angel [1 ]
Frontera, Antonio [1 ]
Quinonero, David [1 ]
Molins, Elies [2 ]
Deya, Pere M. [1 ]
机构
[1] Univ Illes Balears, Dept Quim, E-07122 Palma de Mallorca, Baleares, Spain
[2] CSIC, Inst Ciencia Mat, E-0183 Barcelona, Spain
来源
CRYSTENGCOMM | 2010年 / 12卷 / 02期
关键词
SLIDES;
D O I
10.1039/b913111f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The simple substitution of a hydrogen atom by a fluorine atom in 1-hexyluracil has an enormous consequence on the solid state structure due to the increment in the pi-acidity of the ring.
引用
收藏
页码:362 / 365
页数:4
相关论文
共 25 条
  • [1] Interaction of anions with perfluoro aromatic compounds
    Alkorta, I
    Rozas, I
    Elguero, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) : 8593 - 8598
  • [2] [Anonymous], 1998, C H PI INTERACTION E
  • [3] A QUANTUM-THEORY OF MOLECULAR-STRUCTURE AND ITS APPLICATIONS
    BADER, RFW
    [J]. CHEMICAL REVIEWS, 1991, 91 (05) : 893 - 928
  • [4] Anion-π, Lone-Pair-π, π-π and Hydrogen-Bonding Interactions in a CuII Complex of 2-Picolinate and Protonated 4,4′-Bipyridine: Crystal Structure and Theoretical Studies
    Biswas, Chaitali
    Drew, Michael G. B.
    Escudero, Daniel
    Frontera, Antonio
    Ghosh, Ashutosh
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (15) : 2238 - 2246
  • [5] SIR2004:: an improved tool for crystal structure determination and refinement
    Burla, MC
    Caliandro, R
    Camalli, M
    Carrozzini, B
    Cascarano, GL
    De Caro, L
    Giacovazzo, C
    Polidori, G
    Spagna, R
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2005, 38 : 381 - 388
  • [6] STEREOELECTRONIC EFFECTS OF DEOXYRIBOSE O4' ON DNA CONFORMATION
    EGLI, M
    GESSNER, RV
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (01) : 180 - 184
  • [7] Lone pair-aromatic interactions: To stabilize or not to stabilize
    Egli, Martin
    Sarkhel, Sanjay
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (03) : 197 - 205
  • [8] Energetic vs Synergetic Stability: A Theoretical Study
    Estarellas, Carolina
    Frontera, Antonio
    Quinonero, David
    Alkorta, Ibon
    Deya, Pere M.
    Elguero, Jose
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (13) : 3266 - 3273
  • [9] Farrugia L. J., 1999, Journal of Applied Crystallography, V32, P837, DOI [DOI 10.1107/S0021889812029111, 10.1107/S0021889899006020, DOI 10.1107/S0021889899006020]
  • [10] Anion binding involving π-acidic heteroaromatic rings
    Gamez, Patrick
    Mooibroek, Tiddo J.
    Teat, Simon J.
    Reedijk, Jan
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (06) : 435 - 444