Molecular electrostatic potential dependent selectivity of hydrogen bonding

被引:82
作者
Aakeroey, Christer B. [1 ]
Wijethunga, Tharanga K. [1 ]
Desper, John [1 ]
机构
[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
关键词
SUPRAMOLECULAR CHEMISTRY; ENZYMATIC CATALYSIS; DICARBOXYLIC-ACIDS; SOLID-STATE; COCRYSTALS; CAPSULES; CRYSTALS; SURFACES; DESIGN;
D O I
10.1039/c4nj01324g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of co-crystallizations between four biimidazole based compounds (1,1'-bis(pyridin-4-ylmethyl)-2,2'-biimidazole A1, 1,1'-bis(pyridin-3-ylmethyl)-2,2'-biimidazole A2, 1,1'-bis(pyridin-2-ylmethyl)-2,2'-biimidazole A3 and 1,1'-dibenzyl-2,2'-biimidazole A4) and nine symmetric aliphatic di-acids were carried out in order to determine if a ranking based on calculated molecular electrostatic potential surfaces (MEPS) can be used to effectively assign selectivity in hydrogen-bond based intermolecular interactions. Acceptors A1-A3 are asymmetric ditopic acceptors where two types of nitrogen atoms (pyridine and imidazole) are present, while A4 is a control molecule with only one type of acceptor to rule out any influence of steric factors in the observed structures. 28 of 36 experiments (78% yield) produced a co-crystal, as indicated by relevant changes in the corresponding infrared spectra. Twelve crystal structures of co-crystals of A1-A3 were obtained and every single one displayed primary OH center dot center dot center dot N hydrogens bonds that could be rationalized using the ranking based upon electrostatic potential maps. One crystal structure of A4 was obtained the result of which indicate that the patterns of behaviour established in this family of compounds is not a result of sterics or crystal packing; a simple electrostatic view of hydrogen-bond strength provides a reliable tool for predicting the most likely interactions in a competitive system.
引用
收藏
页码:822 / 828
页数:7
相关论文
共 55 条
[1]   Improving success rate of hydrogen-bond driven synthesis of co-crystals [J].
Aakeroey, Christer B. ;
Desper, John ;
Fasulo, Meg E. .
CRYSTENGCOMM, 2006, 8 (08) :586-588
[2]   The structural landscape of heteroaryl-2-imidazoles: competing halogen- and hydrogen-bond interactions [J].
Aakeroey, Christer B. ;
Wijethunga, Tharanga K. ;
Haj, Mohammad Abul ;
Desper, John ;
Moore, Curtis .
CRYSTENGCOMM, 2014, 16 (31) :7218-7225
[3]   Practical crystal engineering using halogen bonding: A hierarchy based on calculated molecular electrostatic potential surfaces [J].
Aakeroey, Christer B. ;
Wijethunga, Tharanga K. ;
Desper, John .
JOURNAL OF MOLECULAR STRUCTURE, 2014, 1072 :20-27
[4]   Ranking Relative Hydrogen-Bond Strengths in Hydroxybenzoic Acids for Crystal-Engineering Purposes [J].
Aakeroey, Christer B. ;
Epa, Kanishka ;
Forbes, Safiyyah ;
Schultheiss, Nathan ;
Desper, John .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (44) :14998-15003
[5]   Establishing Supramolecular Control over Solid-State Architectures: A Simple Mix and Match Strategy [J].
Aakeroey, Christer B. ;
Panikkattu, Sheelu V. ;
DeHaven, Baillie ;
Desper, John .
CRYSTAL GROWTH & DESIGN, 2012, 12 (05) :2579-2587
[6]   Cyanooximes as effective and selective co-crystallizing agents [J].
Aakeroey, Christer B. ;
Salmon, Debra J. ;
Smith, Michelle M. ;
Desper, John .
CRYSTENGCOMM, 2009, 11 (03) :439-443
[7]   Cyanophenyloximes:: Reliable and versatile tools for hydrogen-bond directed supramolecular synthesis of cocrystals [J].
Aakeröy, CB ;
Salmon, DJ ;
Smith, MM ;
Desper, J .
CRYSTAL GROWTH & DESIGN, 2006, 6 (04) :1033-1042
[8]   Toward high-yielding supramolecular synthesis:: Directed assembly of ditopic imidazoles/benzimidazoles and dicarboxylic acids into cocrystals via selective O-H•••N hydrogen bonds [J].
Aakeröy, CB ;
Desper, J ;
Leonard, B ;
Urbina, JF .
CRYSTAL GROWTH & DESIGN, 2005, 5 (03) :865-873
[9]   Is conformational flexibility in a supramolecular reagent advantageous for high-yielding co-crystallization reactions? [J].
Aakeröy, CB ;
Desper, J ;
Urbina, JF .
CRYSTENGCOMM, 2005, 7 :193-201
[10]   Crystal engineering of hydrogen-bonded assemblies -: A progress report [J].
Aakeröy, CB ;
Beatty, AM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (07) :409-+