Electron distribution in 1-organo-1H-tetrazole-5-thiols. Crystal and molecular structure of 1-methyl-1H-tetrazole-5-thiol and its potassium (18-crown-6) salt

✍ Scribed by Raymundo Cea-Olivares; Omar Jiménez-Sandoval; Simón Hernández-Ortega; Mónica Sánchez; Rubŕn Alfredo Toscano; Ionel Haiduc

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 682 KB
• Volume: 6
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520060118

✦ Synopsis

Abstract

The crystal and molecular structures of both neutral and anionic 1‐methyl‐1H‐tetrazole‐5‐thiol, as its potassium(18‐crown‐6) salt, are reported. In the solid state, the molecular thiotetrazole adopts a planar, dimeric arrangement, in which two neighboring molecules are hydrogen bridged. Each monomeric unit exhibits considerable π electron delocalization over the CN~2~S fragment. The anionic form displays extensive, but not uniform, π electron delocalization within the ring, which also extends to the exocyclic carbon–sulfur bond, the structure being best described as a hybrid. The potassium cation is coordinated to the macrocyclic 18‐crown‐6 ether as expected, but it also interacts with the NCS fragment of the tetrazolethiolate ring.