Engineering polar crystal structures by π-π stacking of N-perfluoroarylbenzimidazoles

被引:9
作者
Althagbi, Hanan I. [1 ]
Lane, Joseph R. [1 ]
Saunders, Graham C. [1 ]
Webb, Samantha J. [1 ]
机构
[1] Univ Waikato, Sch Sci, Hamilton 3240, New Zealand
关键词
Benzimidazole; Polyfluoroarene; pi-pi Stacking; Polar crystal structure; ARENE-PERFLUOROARENE INTERACTIONS; 1/1; COMPLEXES; SINGLE-CRYSTAL; HEXAFLUOROBENZENE; OCTAFLUORONAPHTHALENE; BENZENE; THERMOCHEMISTRY; FLUORINE; PHASE; VAN;
D O I
10.1016/j.jfluchem.2014.07.024
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1-(4-Nitrilo-2,3,5,6-tetrafluorophenyl)benzimidazole, 2, and 1-(2,3,5,6-tetrafluoropyridyl)-2-methyl-benzimidazole, 4, crystallize in the polar space groups Cc and Pca2(1), respectively. Both structures arise from pi-pi stacking interactions. For 2 the stacking gives rise to columns of alternating complementary rings that are approximately orthogonal. For 4 the stacking leads to parallel columns, with the polarity arising from the arrangement of the resulting sheets of molecules, between which there are no pi-pi stacking interactions. The syntheses of2 and 4 and related perfluoroarylbenzimidazoles are also reported. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:88 / 95
页数:8
相关论文
共 50 条
[1]   Synthesis of polyfluorodibenz[b,f][1,4]oxazepines by the cyclization of 2-[(polyfluorobenzylidene)amino]phenols [J].
Allaway, CL ;
Daly, M ;
Nieuwenhuyzen, M ;
Saunders, GC .
JOURNAL OF FLUORINE CHEMISTRY, 2002, 115 (01) :91-99
[2]  
[Anonymous], 1996, SADABS, Program for empirical absorption correction
[3]  
[Anonymous], 1998, SAINT NT
[4]   X-ray diffraction and theoretical studies for the quantitative assessment of intermolecular arene-perfluoroarene stacking interactions [J].
Bacchi, S ;
Benaglia, M ;
Cozzi, F ;
Demartin, F ;
Filippini, G ;
Gavezzotti, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3538-3546
[5]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[6]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[7]   STRUCTURES OF POLYFLUOROAROMATIC COMPOUNDS .3. STATISTICAL COMPARISON OF 2 DETERMINATIONS OF THE CRYSTAL-STRUCTURE OF 2,3,4,5,6-PENTAFLUOROBIPHENYL, A MOLECULE FORMING MIXED STACKS IN THE SOLID-STATE [J].
BROCK, CP ;
NAAE, DG ;
GOODHAND, N ;
HAMOR, TA .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1978, 34 (DEC) :3691-3696
[8]   The preparation and properties of polyfluoro aromatic and heteroaromatic compounds [J].
Brooke, GM .
JOURNAL OF FLUORINE CHEMISTRY, 1997, 86 (01) :1-76
[9]   Mechanisms of reactions of halogenated compounds Part 7. Effects of fluorine and other groups as substituents on nucleophilic aromatic substitution [J].
Chambers, Richard D. ;
Martin, Peter A. ;
Sandford, Graham ;
Williams, D. Lyn H. .
JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (10) :998-1002
[10]   The molecular quadrupole moment: solid state architectures containing organic and organometallic molecules [J].
Clyburne, JAC ;
Hamilton, T ;
Jenkins, HA .
CRYSTAL ENGINEERING, 2001, 4 (01) :1-9