Three Polymorphic Forms of the Co-Crystal 4,4′-Bipyridine/Pimelic Acid and their Structural, Thermal, and Spectroscopic Characterization

被引:67
作者
Braga, Dario [1 ]
Palladino, Giuseppe [1 ]
Polito, Marco [1 ]
Rubini, Katia [1 ]
Grepioni, Fabrizia [1 ]
Chierotti, Michele R. [2 ]
Gobetto, Roberto [2 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Univ Turin, Dipartimento Chim IFM, I-10125 Turin, Italy
关键词
co-crystals; hydrogen bonds; NMR spectroscopy; polymorphism; solid-state structures;
D O I
10.1002/chem.200801051
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three crystal forms of the co-crystal 4,4'-bipy/pimelic acid (bipy: bipyridine), [NH4C5-C5H4N]center dot[HOOC-(CH2)(5)COOH], have been prepared and their relationship investigated by single-crystal X-ray diffraction, variable-temperature X-ray powder diffraction, differential scanning calorimetry and solid-state NMR spectroscopy. Both X-ray and NMR spectroscopic results indicate that no proton transfer takes place, that is, the three crystal forms are true co-crystals of neutral molecules. Forms I and II both convert into Form III at high temperature, Forms II and III being the thermodynamically stable forms at room and high temperature, respectively.
引用
收藏
页码:10149 / 10159
页数:11
相关论文
共 80 条
[11]   Hydrogen bonding interactions between ions: A powerful tool in molecular crystal engineering [J].
Braga, D ;
Maini, L ;
Polito, M ;
Grepioni, F .
SUPRAMOLECULAR ASSEMBLY VIA HYDROGEN BONDS II, 2004, 111 :1-+
[12]   Supramolecular complexation of alkali cations through mechanochemical reactions between crystalline solids [J].
Braga, D ;
Maini, L ;
Giaffreda, SL ;
Grepioni, F ;
Chierotti, MR ;
Gobetto, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3261-3269
[13]   Solid-state versus solution preparation of two crystal forms of [HN(CH2CH2)3NH][OOC(CH2)COOH]2.: Polymorphs or hydrogen bond isomers? [J].
Braga, D ;
Maini, L .
CHEMICAL COMMUNICATIONS, 2004, (08) :976-977
[14]   Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo [2.2.2] octane and dicarboxylic acids of variable chain length: An x-ray diffraction and solid-state NMR study [J].
Braga, D ;
Maini, L ;
de Sanctis, G ;
Rubini, K ;
Grepioni, F ;
Chierotti, MR ;
Gobetto, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (22) :5538-5548
[15]   Assembly of hybrid organic - Organometallic materials through mechanochemical acid-base reactions [J].
Braga, D ;
Maini, L ;
Polito, M ;
Mirolo, L ;
Grepioni, F .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) :4362-4370
[16]   Solvent effect in a "solvent free" reaction [J].
Braga, Dario ;
Giaffreda, Stefano Luca ;
Grepioni, Fabrizia ;
Chierotti, Michele R. ;
Gobetto, Roberto ;
Palladino, Giuseppe ;
Polito, Marco .
CRYSTENGCOMM, 2007, 9 (10) :879-881
[17]   Cis-trans isomerization in crystalline [(η5-C5H5)Fe(μ-CO)(CO)]2 [J].
Braga, Dario ;
Chierotti, Michele R. ;
Garino, Nadia ;
Gobetto, Roberto ;
Grepioni, Fabrizia ;
Polito, Marco ;
Viale, Alessandra .
ORGANOMETALLICS, 2007, 26 (09) :2266-2271
[18]   Making crystals from crystals:: three solvent-free routes to the hydrogen bonded co-crystal between 1,1′-di-pyridyl-ferrocene and anthranilic acid [J].
Braga, Dario ;
Giaffreda, Stefano Luca ;
Rubini, Katia ;
Grepioni, Fabrizia ;
Chierotti, Michele R. ;
Gobetto, Roberto .
CRYSTENGCOMM, 2007, 9 (01) :39-45
[19]   Polymorphism in crystalline cinchomeronic acid [J].
Braga, Dario ;
Maini, Lucia ;
Fagnano, Concezio ;
Taddei, Paola ;
Chierotti, Michele R. ;
Gobetto, Roberto .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (04) :1222-1230
[20]   Solid-state preparation of hybrid organometallic-organic macrocyclic adducts with long chain dicarboxylic acids [J].
Braga, Dario ;
Giaffreda, Stefano Luca ;
Grepioni, Fabrizia .
CHEMICAL COMMUNICATIONS, 2006, (37) :3877-3879