Continuing the search for a non-classical ethyl cation stabilized by organic molecules; the triethyloxonium ion

✍ Scribed by Zagorevskii, D. V.; Sirois, M.; Cao, J. R.; George, M.; Holmes, J. L.; Ross, C. W.

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 730 KB
• Volume: 31
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(199601)31:1<55::aid-jms254>3.0.co;2-3

✦ Synopsis

Triethyloxonium ions, (C,H,),O+, and their deuterated analogues were produced in a tandem mass spectrometer and a Fourier transform ion cyclotron resonance mass spectrometer by ion-molecule reactions in mixtures of ethyl iodide and diethyl ether. Three ion-molecule reactions were identified as the sources of (C,H,),O+, namely (C,H,),O+' + C,H,I + (C,H,),O+ + I' (l), (C,H,),OH+ + C,H,I + (C,H,),O+ + HI (2) and C,H,I+' + (C2H,),0 -+ (C2H5),0+(*C,H,) + 1-(3). Reactions (1) and (3) produced stable intermediate adducts; (2) did not. Metastable (C5HS),0+ ions formed by all these reactions lost C,H,. Ions from reactions (1) and (3) were proposed to have the classical Structure, and this isomer was also generated by the dissociation of the ionized adduct, [(C,H,),O'IC,H,JJ+'. Only C,H, loss from ions produced by reaction (3) showed H-D mixing in the ethyl group originally attached to iodine atom. No firm evidence was found for the participation of a non-classical H-bridged ion.