Testing the limits of synthon engineering: salts of salicylic and sulfosalicylic acid with nucleobases and derivatives

被引：29

作者：

de Vries, Elise J. C. ^{[1
]}

Kantengwa, Sylvia ^{[1
]}

Ayamine, Alban ^{[1
]}

Bathori, Nikoletta B. ^{[1
]}

机构：

[1] Cape Peninsula Univ Technol, Fac Sci Appl, Dept Chem, POB 652, ZA-8000 Cape Town, South Africa

来源：

CRYSTENGCOMM | 2016年 / 18卷 / 39期

基金：

新加坡国家研究基金会;

关键词：

HYDROGEN-BONDING INTERACTIONS; ORGANIC-CRYSTAL STRUCTURES; PROTON-TRANSFER COMPOUNDS; 5-SULFOSALICYLIC ACID; SOLID-STATE; CYTOSINIUM; PATTERNS; PROBABILITIES; DYNAMICS; DATABASE;

D O I：

10.1039/c6ce01534d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthon engineering concepts were tested by using nucleobases and derivatives, namely adenine, cytosine, benzimidazole and fluorocytosine when crystallized with salicylic acid and 5-sulfosalicylic acid. These bases were selected to investigate how the hydrogen bond donor and acceptor groups would influence the crystal structure. Salicylic acid was selected to investigate N-H center dot center dot center dot O hydrogen bonding and synthon formation, while its derivative, 5-sulfosalicylic acid, was selected to see how the sulfonate group would enhance or disrupt these features. Each of the seven complexes obtained was characterized by single crystal X-ray diffraction, which showed that acid-base pairing favored salt formation. All the salicylic acid complexes adopt similar hetero supramolecular synthons, while 5-sulfosalicylic acid forms more complex structures with more than one type of synthon present. Crystal formation using cytosine or fluorocytosine did not result in the predicted synthon formation. This unexpected outcome highlights the current limitations of synthon engineering.

引用

页码：7573 / 7579

页数：7

共 41 条

[1] THE HYDROGEN-BOND AND CRYSTAL ENGINEERING [J].