Hydrogen bonding in crystalline arylazonaphthols

✍ Scribed by Alan R. Monahan; John B. Flannery Jr.

• Book ID: 103014568
• Publisher: Elsevier Science
• Year: 1972
• Tongue: English
• Weight: 373 KB
• Volume: 17
• Category: Article
• ISSN: 0009-2614
• DOI: 10.1016/0009-2614(72)85092-9

✦ Synopsis

The electronic and vibrational spcctrs of trufzs-hydrosyazo~ronlatics show profound differences betvveen the preferred species in solution and those prevalent in the crystalliw solids. The hydrazone + azo tautomers dominate the respective electronic spectra of neutral solutions of these compounds. On the other hand, the lorvest energy clectronic transition of crystalline hydrosyuzo compounds is strongly red-shifted (= 1000 A) relative to that for the dissolved species. Support for the thesis that this anomalous absorption characteristic of crystalline azo compounds has its origin in intermolecularly hydrogen-bonded hydrazone-like agge,oates is found in infrared and Raman spectroscopic studies of the solids, in electronic spectroscopy of solutions in acidic media, and comparison spectra of the amorphous solid compounds.