Molecular arrangements in chiral sheets of N-alkylcholamides bilayered crystals

✍ Scribed by Yukio Hishikawa; Ryousuke Watanabe; Kazuki Sada; Mikiji Miyata

• Book ID: 101295651
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 429 KB
• Volume: 10
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1998)10:7<600::aid-chir8>3.0.co;2-5

✦ Synopsis

Chiral compounds, N-methyl-, N-ethyl-, and N-n-propylcholamides, form crystalline inclusion compounds with water or small organic substances. The compounds were analyzed by X-ray diffraction methods. It was found that the crystals have bilayered structures accumulated by chiral molecular sheets. The chiral molecules associate in a unique head-to-head/tail-to-tail and right-to-left motif to give chiral and amphiphilic sheets. Such sheets stack by adhesions between the hydrophilic sides and between the lipophilic sides. The alkyl groups of the amides prompt the formation of a hydrogen-bonding network between the tails instead of a cyclic one between the head and tail. The guest molecules are accommodated into small cavities between the steroidal side chains. Chirality 10: 600-618, 1998.